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45 Fun & Best Things to Do in Chicago, Illinois

The City of Chicago is a multicultural metropolis full of Midwestern hospitality, deep-dish pizza, a love of Lake Michigan, and a deep appreciation for art and culture. As the country’s third largest city, Chicago is often glossed over for the ritzier New York City or the more glamorous Los Angeles. But the Windy City is every bit as fascinating and well worth a visit.

The city is well-known for its magnificent architecture, historical places, and museums, as well as its food. Chicago is also a city dedicated to its blue-collar roots. While we may be a major city, neighborhoods throughout Chicago are like their own little towns. We have a dedication to our neighbors, building a community, and making Chicago the greatest city in the world.

From Millennium Park, the Chicago Symphony Orchestra, the Crown Fountain, the Navy Pier Beer Garden, and the Art of the Architecture walking tour, Chicago is a masterpiece.

These are some of our favorite things to do in Chicago, no matter if you are a first-timer or a frequent visitor. Once you’ve experienced this magnificent city, you’ll understand why its residents love it so much.

Table of Contents


  • Most significant landmark – Millennium Park
  • Best free activity – Lincoln Park Zoo
  • Best activity for kids – Shedd Aquarium
  • Best activity for adults – Garfield Conservatory
  • Best food – Deep dish pizza
  • Best all-around activity – Lake Michigan tour
  • Best all-around accommodation – Kimpton Gray Hotel Chicago

Fun & Best Things to Do in Chicago, Illinois

1. Check Out Millennium Park

The amphitheater space at Millennium Park
CK Foto / Shutterstock

If you’re in Chicago, make sure to see Millennium Park. This public park in downtown Chicago is one of the most visited places in the city. Visitors flock here for photos while locals come by for events like Broadway in the Park or Chicago Symphony Orchestra special concerts.

The giant reflective sculpture known as Cloud Gate or The Bean, as well as the Crown Fountain by Jaume Plensa, are the most visited tourist attractions in Millennium Park. Plus during the wintertime, you can ice skate here or visit the city’s Christmas tree.

The Chicago Jazz Festival is one of the most iconic jazz festivals in the United States and is located right in the heart of Millennium Park. It is a free event that takes place every year in late August or early September. Jazz has a significant history in Chicago, which is recognized by the festival that celebrates acclaimed artists as well as up-and-comers.

Like the Statue of Liberty for New Yorkers, Millennium Park is a similar figure for Chicagoans. We generally don’t go out of our way to come here unless people are visiting from out of town or an event is going on.

2. Take Photos of the Chicago Skyline

Best Things to Do in Chicago

The city skyline in Chicago is one of the most famous in the world and for good reason. Chicago architecture and the design of the city are truly unique and iconic. With the Chicago River running through the skyscrapers, you’ll be hard-pressed to not find a gorgeous view from any angle.

Chicago’s skyline has been featured in countless movies and TV shows which makes it such an iconic view. The best way to get a good view of the Chicago skyline is from one of the many observation decks in the city, such as the Willis Tower or 360 Chicago. Or if you are out by Shedd Aquarium, the view of the city from the walkway near the aquarium is one of the best.

You can even take a cruise on Lake Michigan or the Chicago River to get an up-close and personal view of the skyline. If you want to enjoy the skyline during your stay, check out the Radisson Blu at the Aqua Building or the historic Chicago Athletic Association.

See Related: Best Places to Travel in Your 20s in the US

3. Get Wild at Lincoln Park Zoo

A Polar Bear at Lincoln Park Zoo

Address: 2400 N. Cannon Drive, Chicago, IL 60614

Lincoln Park Zoo is one of the oldest zoos in North America. Founded in 1868, this free Chicago zoo is home to over 1,200 animals, which makes it an excellent place to visit with children. Especially at Christmastime when the zoo does its annual ZooLights event, there’s never a bad time to visit.

With its own restaurants, cafes, and food stands throughout the zoo, it’s easy to spend an entire day here. It is one of my favorite spots in the city to bring visitors, especially my friends with little kiddos in tow.

The Lincoln Park Zoo also offers educational programs and different events throughout the year, making it a great way to learn more about the animal kingdom. Some of those seasonal events include beer, wine, and cocktail-focused programs for zoo-loving adults around the city.

Staying in the neighborhood is a piece of cake too. Near the zoo is the charming, European-style Villa D’Citta. This cozy B&B is a brief walk from other Lincoln Park establishments, plus it’s in a great, central location to access other areas of the city as well.

4. Visit the Museum Campus of Chicago

The interior of the Field Museum
Jim Lambert / Shutterstock

Address: 337 E Randolph St, Chicago, IL 60601

Are you looking for a unique way to experience the cultural and educational offerings of the Windy City? The Museum Campus of Chicago is one of the city’s most popular tourist destinations on the lakefront at Grant Park. Unsurprisingly, this is where you’ll find many Chicago museums.

The campus is home to the Adler Planetarium, The Shedd Aquarium, the Field Museum of Natural History, and Soldier Field. If you’ve never seen Shedd or the Field Museum before, be prepared to be wowed. These buildings are works of art containing some of the best exhibits in the country.

You may be surprised to see some of the architecture around the campus in Chicago. They look like they’ve been transported from elsewhere in the world. We’re so proud to be home to so many incredible museums all in one place.

See Related: Best Museums in the US to Visit

5. The Field Museum of Natural History

Entrance to Field Museum of Natural History, Chicago
Susan Montgomery /

Address: 1400 S Lake Shore Dr, Chicago, IL 60605

The Field Museum of Natural History is one of the most popular tourist destinations in Chicago and is probably the best natural history museum in the country. It is home to some of the most impressive natural history exhibits in the world, with over 4.6 billion years of history on display.

Commonly referred to simply as The Field Museum, this space also features special exhibits on Ancient China, the Qing Dynasty, an interactive fossil lab where visitors can learn about dinosaurs and other ancient creatures, and Dioramas Hall which features realistic recreations of worldwide habitats.

In addition to these displays, there are also rotating temporary exhibitions on topics ranging from climate change to wildlife conservation. Plus, nighttime events bring the museum to life in new ways for locals who have been here countless times – like Dozin’ with the Dinos which includes a museum sleepover!

The Field Museum is a great place to learn about the history of our planet and the various cultures that have inhabited it. With so much to see and do, the Field Museum is sure to please everyone in the family.

6. Cloud Gate at Millennium Park

Cloud Gate a Millennium Park

Address: 201 E Randolph St, Chicago, IL 60602

The star of Millennium Park is, undoubtedly, the enormous public sculpture by Anish Kapoor. Cloud Gate was created in 2006 by the artist and is known as “The Bean” because it resembles a bean. Its round arch includes 161 reflective stainless steel plates which people love to take selfies in front of.

This sculpture is hugely popular with tourists. It has also been used as the backdrop for various fashion shoots and television commercials. In 2012, Cloud Gate was surveyed as part of the Art in Chicago Public Art Survey and now even has a sibling sculpture in New York City. It is also a popular spot for many of the city’s best walking tours.

Although Cloud Gate is the star attraction of Millennium Park, there are other things to appreciate here as well. If you visit Millennium Park in the summertime, expect to wait a while to get your photo with Cloud Gate if you want a certain angle. Crowds around the sculpture are always huge in the summer.

My favorite accommodation downtown which is beyond luscious for any traveler is the Kimpton Gray Hotel. Housed in a historic building, the Kimpton Gray is chic, right by some of the city’s theaters that host touring shows, and right in the heart of downtown.

7. Take a Boat Cruise on Lake Michigan

Boat cruising off the Lake Michigan shoreline in Chicago
Vladislav Gajic / Shutterstock

Lake Michigan is one of the five Great Lakes of North America and the only one located entirely within the United States. At its deepest point, it is 1,333 feet (406 m) deep. While it is a lake, visitors are often astounded at its size. But something you have to know about Chicago is that Chicagoans love Lake Michigan.

Many Chicago marinas and tour companies offer boat cruises, as well as other excellent water activities in Chicago. Swimming, fishing, kayaking, and windsurfing are also popular at one of our many beaches.

Take a moment to unwind and relax while a captain takes you up and down the Lake Michigan shoreline, highlighting landmark buildings and examining a rich historical city. If you want more insights into Chicago’s unique landscape, consider taking an architecture river cruise along the Chicago River which feeds from the lake. (You read that correctly, our river runs backward from the lake.)

8. Try Chicago-Style Hot Dogs

Chicago Dog

Chicago is well-known for many things, from its Prohibition-era speakeasies to its championship sports teams. But one of Windy City’s most iconic exports is Chicago-style hot dogs.

This all-beef frankfurter is served on a poppyseed bun and topped with a plethora of toppings, including yellow mustard, onions, relish, tomato, sport peppers, and a dill pickle spear. It is not, however, ever covered in ketchup. Chicagoans have a lot of opinions about ketchup on hot dogs.

While this may sound like a mouthful, the Chicago Dog is surprisingly easy to eat – and even more delicious. So when you’re in Chicago, be sure to swing by a local hot dog stand and give this classic dish a try — just don’t ask us for ketchup.

See Related: Strange Foods in America You Should Try

9. Eat World-Famous Deep Dish Pizza

Milly's Pizza in the Pan, Chicago Deep Dish

Chicagoans and New Yorkers have a bone to pick with one another about pizza. New Yorkers like their easy-to-eat-while-walking thin crust while Chicagoans clamor for deep-dish. Our type of pizza is different than your average pizza because it has a deep crust that is usually stuffed with gooey cheese.

The deep-dish pizza was invented in the 1940s at Pizzeria Uno and has been a Chicago staple ever since. If you’re looking for a cheesy, filling meal, deep-dish pizza is the way to go. Just don’t call it a casserole to a local.

And, if you’re in Chicago, you might as well try the world-famous deep-dish pizza from Pizzeria Uno, Giordano’s, or Lou Malnati’s. If you ask me, Giordano’s is the best, though locals get pretty heated about whether Lou’s is better than Giordano’s or vice versa. Obviously, we have a lot of strong food-based opinions.

10. The Art Institute of Chicago

The Art Institute of Chicago with one of its lion statues
Brent Hofacker / Shutterstock

Address: 111 S Michigan Ave, Chicago, IL 60603

The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It was founded in 1879 and is located in the Loop downtown off Michigan Avenue. Chicago’s Art Institute is one of the city’s shining gems.

A world-class art museum, with the world’s greatest collection of Impressionist Art outside of France, the Institute is a staple in the city’s cultural community. The Art Institute of Chicago is also one of only three American museums with a Vincent van Gogh painting in their permanent collection. Some other popular exhibits at the Art Institute of Chicago include:

  • Ancient Egyptian Art
  • American Art
  • Art of the Ancient Americas
  • Asian Art

The Art Institute of Chicago is open from 10:30 am to 5 pm Sunday through Thursday and 10:30 am to 8 pm on Friday and Saturday. Admission is paid but free for children under 14. Grab a skip-the-line ticket to avoid the lines and make the most of your visit to this world-class art museum.

See Related: Best Walking Tours in Chicago

11. Catch a Baseball Game or Concert at Wrigley Field

Statue In Front of Wrigley Field in Chicago
FiledIMAGE / Shutterstock

Address: 1060 W Addison St, Chicago, IL 60613

The Chicago Cubs play at the second-oldest baseball stadium after Boston’s Fenway Park. Opened in 1914, Wrigley Field, often known as “Friendly Confines” after legendary Ernie Banks, is renowned for its ivy-covered outfield walls and a manually-operated scoreboard.

It may come as a surprise that it’s located in a residential neighborhood, aptly known as Wrigleyville, surrounded by brownstone townhomes rooftops, bars, and restaurants. During baseball season, visiting fans can watch as the Cubs battle it out with their opponents—or enjoy some hotdogs and beer while soaking up the atmosphere of this legendary stadium.

Besides baseball, Wrigley Field also hosts concerts for popular music artists. Previous performers have included Paul McCartney, The Rolling Stones, Lady Gaga, Bruce Springsteen, and Elton John. If you are in Chicago during summer, make sure to check out the concert schedule and catch a game or two at this historic ballpark.

If you aren’t up for a game, you can take a guided tour of Wrigley Field. On non-game days, tours include the press box, bleachers, locker rooms, dugouts, and sometimes (not always) a chance to walk on the baseball field.

12. John Hancock Center

Titled viewing area at John Hancock Observatory
Alex Cimbal / Shutterstock

Address: 875 N Michigan Ave, Chicago, IL 60611

The John Hancock Center is a 100-story Chicago skyscraper and is one of the tallest buildings in the world, as well as the ninth-tallest building in the United States. It was officially renamed 875 North Michigan Avenue in 2018. Though just like with Willis Tower, which we still refer to as Sears Tower, Chicagoans still call it The John Hancock.

The center’s 360 Chicago observation deck is on the 94th floor of the building and provides panoramic views over the city. The view deck climbs 1,390 feet, giving visitors the chance to see four neighboring states, including Indiana and Wisconsin. You can also relax at the bar while watching the sunset after spending time in the John Hancock observatory areas.

At the base of the building, there are several chain restaurant locations including The Cheesecake Factory and Benihana. You’re also just a few blocks away from The Art Institute since 875 North Michigan Avenue is in the heart of downtown Chicago.

See Related: Best Family Vacations on a Budget

13. Witness World-Renowned Theater

The Chicago Theatre at night
Triyansh Gill / Unsplash

Address: 175 N State St, Chicago, IL 60601

Whenever people ask me why I chose Chicago over New York as a theater writer and lover, I tell them: Chicago is where great theater is born. Chicago is home to over 200 theater companies and year after year creates some of the grittiest theatrical work in the world.

Whether you’re seeing a great performance at the iconic Chicago Theatre, bopping to Broadway at the Cadillac Palace Theatre, or experiencing the classics at Chicago Shakespeare Theater, you’re seeing the best of Chicago. Though our storefront scene is what makes our theater truly special.

Chicago’s storefront theaters are what truly set us apart from theater anywhere else. These intimate spaces, where you are sometimes only inches from the performers, will give you a whole new perspective on life. So while The Den down in Wicker Park or the Tony Award-winning Court Theatre in Hyde Park might be small compared to the Chicago Theatre, they are still mighty.

14. Frolic in the Sand at North Avenue Beach

North Avenue Beach in Chicago
f11photo / Shutterstock

Address: 1600 N Lake Shore Dr, Chicago, IL 60613

You might be surprised to find out that one of the best things to do in Chicago in the summertime is hanging out at the beach. North Avenue Beach is one of the most popular beaches in Chicago and a great place to enjoy the sun, swim, and just relax.

This beach offers many activities, such as jet skiing, parasailing, kayaking, and more. If relaxation is more your speed, then no worries; you can rent lounge chairs right on the water’s edge so you can kick back and soak up some sun without any distractions.

The beach is easily reached from downtown Chicago, located just a few blocks north of the Magnificent Mile. Once you’re there, you’ll find plenty of space to spread out your towel and relax in the sun.

If you’re looking to cool off, North Avenue Beach has a designated swimming area with a lifeguard on duty. And when you’re ready to grab a bite to eat or drink, there are plenty of options along the beach too.

15. Dine in the Ultimate Chicago Skyline Experience at The Signature Room

A view from a table at The Signature room
The Signature Room at the 95th / Facebook

Address: 875 N Michigan Ave, Chicago, IL 60611

If you’re looking for an incredible place to enjoy a drink and an amazing view of Chicago, the Signature Room at the 95th is definitely worth a visit. Located on the 95th floor of the former John Hancock Center, the Signature Room offers an unparalleled 360-degree view of the city.

The atmosphere is upscale but relaxed, making it perfect for a date night or happy hour with friends, though they do have a business casual dress code. They request no gym shoes, beachwear, or ripped jeans, and shorts and sandals are not allowed at dinner. However, The Signature Lounge at the 96th is more casual.

In addition to an impressive selection of cocktails, the Signature Room also offers an extensive menu of small plates and entrees. Whether you’re looking to enjoy a few drinks or have a full meal, the Signature Room is one of the best spots to grab a bite with a view.

16. Visit the Spirit Statue and Catch a Game at the United Center

The Spirit Statue Outside United Center

Address: 1901 W Madison St, Chicago, IL 60612

The Spirit is a statue of Michael Jordan located on the Near West Side outside the United Center. Unveiled on November 1, 1994, the Spirit Statue has since become one of the most recognizable landmarks in Chicago. Jordan’s bronze and granite statue is a must-see for any fan of Chicago’s legendary basketball player.

The Spirit statue is situated in a plaza that also features a statue of Jerry Reinsdorf, the owner of the Chicago Bulls and Chicago White Sox. The plaza is located just outside the main entrance to the United Center, and it is a popular spot for fans to take pictures before or after Bulls games.

At the base the statue has a quote from the film A River Runs Through It: “At that moment I knew, surely and clearly, that I was witnessing perfection. He stood before us, suspended above the earth, free from all its laws like a work of art, and I knew, just as surely and clearly, that life is not a work of art, and that the moment could not last.”

17. The Historic 63rd Street Beach

People at the 63rd Street Beach in Chicago

Address: 6300 S. Lake Shore Dr, Chicago, IL 60637

The 63rd Street Beach is one of the oldest beaches in Chicago, established in 1913. It’s a popular spot for destination weddings and other special events. The 63rd Street Beach House is a historical landmark and features an auditorium, gymnasium, as well as public locker rooms.

The beach is also a great spot for swimming, sunbathing, and picnicking. Visitors can also enjoy fishing, volleyball, and basketball. It’s simply the perfect place to enjoy the breathtaking views of Lake Michigan.

On the southern end of the beach, visitors can also use non-motorized water vehicles. That includes canoes, kayaks, and paddleboards. Although it can be busy in the summer, it’s still often less crowded than North Avenue. This is definitely one of the lesser-known things to do in Chicago.

18. Take in the Chicago Food Truck Scene

Pastrami Sandwich in Chicago

Chicago is a food lover’s paradise, and one of the best ways to experience the city’s culinary scene is to check out the food trucks. Chicago’s food trucks offer various cuisines, from hot dogs and pizza to Vietnamese and Mexican. And Chicagoans love their food trucks – you’ll often see long lines at popular trucks like Chicago Lunchbox and Tamale Spaceship.

You’ll find most of the food trucks in Chicago’s downtown Loop area, though they disperse elsewhere throughout the week. Other areas that food trucks love are also in neighborhoods like Hyde Park and Lincoln Park.

If you’re looking to experience the best of Chicago’s food truck scene, be sure to check out the Chicago Food Truck Fest. Held annually in June, the fest features some of the city’s best food trucks, as well as live music and entertainment. It’s the perfect way to sample the best of what Chicago has to offer.

19. The Amazing Concerts at Hyde Park

Band Playing in Hyde Park of Chicago

From the Hyde Park Jazz Festival to Summerfest, this neighborhood is always alive with arts and culture. Major events like the festivals aside, there are smaller community concerts that give you a real glimpse into the spirit of Hyde Park.

For example, the concerts at Rockefeller Chapel and Bond Chapel at the University of Chicago are not to be missed. Often in the classical vein, you can hear students and professionals fill the chapels with musical serenity. It’s also the perfect excuse to experience the stunning beauty of the chapels.

Chapel concerts are held in the summer and are free for the public. When you’re finished listening to music anywhere in Hyde Park, you should explore this incredible neighborhood. Find out why so many artists and Nobel Prize winners have called it home.

20. Wander Around Navy Pier

An aerial view of Navy Pier
f11photo / Shutterstock

Address: 600 E Grand Ave, Chicago, IL 60611

Navy Pier is a stunning landmark along the lake In Chicago. It’s a great place to visit for tourists and offers a wonderful view of the city’s skyline. This 3300-foot pier juts out into Lake Michigan and features an array of activities such as carnival rides, fireworks shows, boat tours, and sightseeing cruises.

There are also many cultural programs available at Navy Pier, as well as amazing food options, making it one of the most fun things to do in Chicago with kids. If you want something even more exciting, take a spin on the Centennial Wheel for panoramic views of downtown Chicago. There are plenty of attractions for both children and adults, as well as delicious food choices.

A visit to Navy Pier wouldn’t be complete without a stop at one of the many restaurants and shops inside the pier building. Plus, if you’re searching for a romantic destination, Navy Pier is a must-see. You can even see a show at Chicago Shakespeare which resides on the pier.

If you’re looking for a place to stay along Navy Pier, the lovely Sable at Navy Pier Chicago is your best option. This hotel has some of the best views of the lake of any accommodation in the city. After all, you’re right on the water!

21. See the Fishes at Shedd Aquarium

People at the Carribbean Reef exhibit at Shedd Aquarium
James Kirkikis / Shutterstock

Address: 1200 S Dusable Lk Shr Dr, Chicago, IL 60605

Shedd Aquarium is rightly located on the shores of Lake Michigan and is one of the world’s largest indoor aquariums. It was founded in 1930 and built as Neptune’s Temple in the style of a Grecian temple. If the architecture reminds you of The Field Museum, that makes sense since the same firm designed them.

Its tanks house over 32,000 animals from over 1,500 species, including sharks, jellyfish, sea horses, penguins, and more. This historic aquarium, with its octagonal original floorplan, is one of the most open aquariums you’ll ever experience. It is one of Chicago’s finest institutions and is a favorite among Chicagoans.

Plus, visitors can get up close with animals during encounters like Stingray Touch or Penguin Encounters! You can even feed the stingrays or touch sturgeon and sea stars! Plus, who wouldn’t want to meet a penguin?

22. Check Out Sweet Mandy B’s Cupcakes

Multicolored cupcakes in a row at Sweet Mandy B's
Sweet Mandy B’s / Facebook

Addresses: 1208 W Webster Ave and 254 E Ontario St

Sweet Mandy B’s Cupcakes is a must-visit for anyone in the area. The cupcakes are old-fashioned and homemade, and the shops have bright, colorful décor that is sure to attract children. In addition to the great taste and fun atmosphere, Sweet Mandy B’s offers a wide variety of flavors and toppings.

They currently have two locations. One in Lincoln Park off Webster Ave and the other in the Streeterville neighborhood on Ontario. If you’re staying downtown, the Streeterville location will likely be the closest for you.

So whether you’re looking for a classic vanilla cupcake or something more adventurous like a chocolate-covered strawberry, Sweet Mandy B’s is sure to have something to satisfy your sweet tooth. Next time you’re in town, be sure to stop by Sweet Mandy B’s Cupcakes for an unforgettable treat.

23. Indulge in the Chicago Diner Scene (Especially the Shakes)

A Mint Hopper concrete custard treat from Lickety Split
Lickety Split / Facebook

Out-of-towners may think that Chicago is most recognized for its architecture, deep-dish pizza, and meat-heavy cuisine. What many visitors to the Windy City are unaware of, though, is our city’s fantastic diner scene.

While there are many great options to choose from, The Chicago Diner is a must-visit for anyone looking for a delicious, hearty meal. The Chicago Diner is an all-vegetarian establishment, which may come as a surprise to some. However, what they lack in the meat, they more than make up for in flavor.

Other diners all over the city have equally incredible offerings, especially on the ice cream treat front. Lickety Split is my personal favorite. They serve custard which you’ll find all over the Midwest. Custard has a richer consistency and flavor than ice cream because it’s made with eggs and Midwesterners love custard.

24. Shop and Dine Along the Magnificent Mile

Cars zooming along the road on the Magnificent Mile
dibrova / Shutterstock

The Magnificent Mile is home to some of the most recognizable landmarks in Chicago like Tribune Tower and the Wrigley Building. This stretch of Michigan Avenue along the Chicago River is known for its upscale stores, iconic landmarks, and stunning views. Whether you’re visiting for a day or a weekend, The Magnificent Mile is at the top of things to do in Chicago for shoppers.

The Magnificent Mile is a six-block stretch of Michigan Avenue in downtown Chicago. Some of the shops you’ll find on the Magnificent Mile include high-end retailers like Saks Fifth Avenue and Neiman Marcus, as well as more budget-friendly stores like H&M and Uniqlo.

Along the Magnificent Mile, you’ll find 275 eateries and over 450 retail stores, ranging from flagship locations for Nike and Zara to some of the Windy City’s most well-known boutique shops. You could even take a stroll along the riverwalk along the Chicago River in summer to take in the beautiful river scenes.

25. See the Chicago Bears at Soldier Field

An aerial view of Soldier Field
Felix Mizioznikov / Shutterstock

Address: 1410 Special Olympics Dr, Chicago, IL 60605

Soldier Field is a football stadium located on the South Side of Chicago. No trip to Chicago would be complete without catching a game of the Chicago Bears — until 2033 when the team will likely leave for their new home in Arlington Heights. This iconic football team has been playing since 1919 and is one of the oldest teams in NFL history.

Soldier Field is one of the Windy City’s most famous landmarks and was built to promote sports in the area. The stadium has a capacity of more than 100,000 people and has hosted several concerts, thrill shows, fireworks shows, and other events.

If you’re looking for a fun thing to do in Chicago, take a look at potential events and tickets for a show at Soldier Field. It’s a marvelous stadium that offers excellent views of Windy City.

26. Take a Photo Break at Buckingham Fountain

The Buckingham Fountain at dusk
Vlad G / Shutterstock

Address: 301 S Columbus Dr, Chicago, IL 60605

The centerpiece of Grant Park is the Grant Garden, which provides stunning vistas of the city. One of the must-see attractions in Grant Park is Buckingham Fountain, an awe-inspiring Chicago landmark located at the park’s center. Folks can forget it exists, but seeing it is one of my favorite things to do in Chicago with out-of-towners.

Built in 1927, this fountain was designed by Edward Bennett and financed by Kate Sturges Buckingham as a memorial to her brother. It features four sets of sea horses representing Lake Michigan and the four states bordering it (Illinois, Wisconsin, Indiana, and Michigan) and an impressive central jet that shoots water 136 feet into the air every hour.

The Buckingham Fountain was erected in Georgia pink marble in 1928 and is almost 8 meters tall with more than 200 jet engines measuring 85 meters across. There’s no better way to get a panoramic view of Grant Park than from Buckingham Fountain.

See Related: Best Places to Visit in the US

27. Marvel at the DuSable Bridge

DuSable Bridge opening with a sailboat going under it
Mark Baldwin / Shutterstock

Address: 333 Michigan Ave, Chicago, IL 60601

The DuSable Bridge, formerly known as the Michigan Avenue Bridge, is a bascule, or moveable bridge, linking the north and south sides of Chicago over the Chicago River. This bridge is also one of the top things to see in Chicago because you get incredible views of the river from it and an artistic representation of the city’s history.

DuSable Bridge is a magnificent piece of architecture built by the best engineers of its time, especially due to its mechanical power. It is built in the Beaux Arts style, much like the 1909 plans for Chicago which were largely Parisian. The bridge is meant to mirror the aesthetic of the Alexander III Bridge in Paris.

The bridge’s four houses on each corner showcase a different momentous time in Chicago’s history. These houses depict the arrival of James Marquette and Louis Joliet, first settlers Jean Baptiste Point du Sable and John Kinzie, The Battle of Fort Dearborn, and the rebuilding of the city after the Chicago Fire of 1871.

28. Visit the Book Cellar

Book Cellar in Chicago

Address: 4736 N Lincoln Ave, Chicago, IL 60625

The Book Cellar is a community-based, independent bookstore in Chicago that has been around for over twenty years. It’s located in the heart of the Lincoln Park neighborhood, and it’s definitely worth a visit if you’re in the area.

The Book Cellar has an extensive selection of both new and used books, and they also host a variety of events, including readings, signings, and discussions. There are so many genres of books at this beloved Lincoln Park institution that you will have to try not to find something to your liking.

In addition to being a great place to find your next read, the Book Cellar is also home to a cozy cafe, so you can enjoy a cup of coffee or tea while you browse the shelves. Whether you’re a lifelong reader or just looking for a new place to relax, the Book Cellar is definitely worth checking out.

29. Try an Italian Beef Sandwich

Italian Beef Sandwich

We’ve already dedicated a lot of time to Chicago’s food scene, but we aren’t done. We haven’t even talked about Italian beef yet! Italian beef is a sandwich originating from Chicago, made of thinly sliced roast beef simmered in a seasoned broth and served on an Italian roll or Italian-style bread.

The sandwich’s creation is often attributed to Italian immigrants who settled in Chicago’s Little Italy in the early 1900s. Italian immigrants were known for bringing their culinary traditions with them when they settled in new areas, and the Italian beef sandwich is thought to be a product of this migration.

The sandwich became popular among Italian-American immigrants as a way to stretch their meager food budgets and soon became a favorite among the wider population of Chicago. Today, the Italian beef sandwich is a staple of the city’s food culture and can be found at most restaurants, cafes, and delis.

30. Experience the Museum of Science and Industry

The Museum of Science and Industry in Chicago from the Lake
Thomas Barrat / Shutterstock

Address: 5700 S Dusable Lake Shore Dr, Chicago, IL 60637

The Chicago Museum of Science and Industry is one of the largest science museums in the world. With over 35,000 artifacts on display, it is a veritable feast for the eyes of technology lovers and history buffs alike. The museum is dedicated to inspiring the inventive genius in all of us, and it certainly succeeds in this goal.

Plus the building itself is a historic artifact. Originally built for the 1893 World’s Fair in Chicago as the Palace of Fine Arts, this is one of the only remaining pieces left from the fair. During the fair, it housed all kinds of artwork, which is a bit ironic now that it houses scientific discoveries instead.

From its world-famous Hindenburg exhibit to hands-on learning labs, the Museum of Science and Industry is a must-visit for any Chicago traveler with a curiosity about the world around them. So whether you’re looking to explore the inner workings of a steam engine or learn about the latest advances in robotics, be sure to add the Museum of Science and Industry to your Chicago itinerary.

31. Reach for the Stars at Adler Planetarium

The exterior of Adler Planetarium
Henryk Sadura / Shutterstock

Address: 1300 S Dusable Lk Shr Dr, Chicago, IL 60605

Adler Planetarium is a world-renowned astronomical museum on Lake Michigan’s shores. The Adler Planetarium houses three theaters, a vast collection of scientific instruments, and enough exhibit space to accommodate large-scale exhibitions. Adler Planetarium offers visitors a chance to explore our universe through numerous interactive exhibits.

It was founded in 1930 by astronomer Max Adler as part of The Century Of Progress International Exposition World’s Fair celebration honoring Chicago’s centennial anniversary, and it’s been teaching people about astronomy ever since. The Adler is one of the few places where visitors can see planets, stars, and galaxies up close and offers an array of educational programs that are sure to enlighten and entertain visitors of all ages.

You can explore space topics like black holes and galaxies or take a virtual field trip through our solar system in the Grainger Sky Theater. This planetarium is one of the most unique things to do in Chicago, especially for anyone interested in astronomy or space exploration.

32. Experience the Stunning Chicago Cultural Center

Inside the Chicago Cultural Center

Address: 78 E Washington St, Chicago, IL 60602

The Chicago Cultural Center is a hub for all kinds of cultural events, including art exhibitions. What attracts the most visitors here are the two beautiful stained-glass domes and galleries, which make the hall look magnificent. If you are planning to organize an event in Chicago, then the Chicago Cultural Center will be the best choice for you.

When it opened in 1897, the cultural center became the country’s first free municipal cultural center. It was designed in the neoclassical style with touches of Italian Renaissance as well. It is truly one of the most beautiful spots in the city.

It is still free to visit and is open every day from 10 am to 5 pm. Holidays are the only days the museum is closed. Though you could spend all day gazing at the art around the center, this is also a spot you could visit in just an hour too.

33. Enjoy the Chicago Lakefront Trail

Chicago Lakefront Trail on Lake Michigan
James Kirkikis / Shutterstock

Chicago’s Lakefront Trail is one of the city’s most popular attractions. The 18.5-mile linear park offers stunning views of Lake Michigan, as well as a variety of activities for visitors to enjoy. Whether you’re looking to take a leisurely stroll or go for a jog, the Chicago Lakefront Trail is the perfect place to do it.

Because it runs so far through the city, zigzagging through different neighborhoods, it offers easy access to some of the best the Windy City has to offer. It’s best visited during the warmer months, though be careful if it’s a very windy day. Getting smacked in the face by lake water mist at a high speed hurts!

And if you’re visiting Chicago during the summer, be sure to cool off with a swim on one of the many beaches along the trail. Whether you’re a local or a visitor, the Chicago Lakefront Trail is sure to provide an enjoyable experience.

34. The Chicago Water Tower

The Water Tower at nighttime
Rudy Balasko / Shutterstock

Address: 806 Michigan Ave, Chicago, IL 60611

The Chicago Water Tower is one of the best-known landmarks in the Windy City. Built between 1867-1869 in the Gothic Revival Style, it was originally designed to house a large water pump that drew and regulated water from Lake Michigan. The Water Tower was one of the buildings that survived the Chicago Fire and became the most iconic of the surviving structures.

Today, the Water Tower is home to an art gallery called The City Gallery and is a popular tourist stop. It is a small gallery, but it’s well worth a stop on any Chicago itinerary. Even if it’s just to explore the historic building.

Visitors can enjoy stunning views of the city from the top of the tower, and the gallery features a rotating selection of artwork from local artists. Together, the Water Tower and City Gallery are must-see Chicago attractions for anyone visiting, especially if you’re downtown.

35. Visit the University of Chicago

Library at The University of Chicago

Address: 5801 S Ellis Ave, Chicago, IL 60637

The University of Chicago is one of the world’s premier research universities, offering an education combining the best American and German systems. The University was founded in 1890, and since then it has been at the forefront of intellectual inquiry. Some of its notable alumni include Thomas Sowell, Roger Ebert, Carl Sagan, and Marilu Henner.

Today, the University offers programs in nearly every field of study, making it one of the best places to get a comprehensive education. If you are planning to study abroad, the University of Chicago should definitely be on your list of schools to consider.

What makes the University of Chicago such an interesting place to visit is that its architecture has such a wide range of aesthetics. From Gothic to Contemporary styles, the campus reflects the school’s varied specialties. You can even take a walking tour of the campus to learn more about the campus and its incredible beauty.

See Related: Most Famous Historical Landmarks in the USA

36. See the City from Above at Willis Tower

Willis Tower and Skyline at NIght

Address: 233 S Wacker Dr, Chicago, IL 60606

Willis Tower, formerly known as the Sears Tower, is one of Chicago’s most iconic landmarks. Standing 110 stories tall, it was once the tallest building in the world, though dozens of skyscrapers now hold titles above it. But even today, it’s still pretty remarkable as it towers tall over the city of Chicago.

Chicagoans still call Willis Tower by its old name, Sears Tower, because we haven’t gotten over the name change. Willis Tower is best known for the Skydeck Chicago, which provides visitors with incredible 360-degree views of the city. On a clear day, you can see up to 50 miles away from the Skydeck.

The Skydeck is also home to the popular Ledge, a glass-enclosed balcony that extends four feet outside of the building, offering visitors a truly unique and thrilling experience. If you’re looking for an unforgettable view of Chicago, be sure to add the Willis Tower to your list of places to visit in the Windy City.

37. Get to Know the City at the Chicago History Museum

Chicago History Museum
Thomas Barrat /

Address: 1601 N Clark St, Chicago, IL 60614

Chicago’s history is rich and fascinating, and there’s no better place to learn about it than at the Chicago History Museum. It is the city’s oldest cultural institution since the Chicago Historical Society’s original museum came about in 1856. That original museum was a victim of the Chicago Fire and the society, unfortunately, suffered a second fire that destroyed much of its remaining collections.

Although missing much of the original collection, the museum features exhibits on a wide range of topics, from the city’s role in the American Revolution to the Great Chicago Fire. Some of their permanent collections include Chicago: Crossroads of America, Lincoln’s Chicago, and Facing Freedom in America.

There’s also a large collection of artifacts on display, including pieces from the 1893 World’s Exposition. Whether you’re a Chicagoan or just visiting, the Chicago History Museum is always worth a visit.

38. Stroll Around Grant Park

Grant Park in Chicago, Illinois

Address: 337 E Randolph St, Chicago, IL 60601

As far as cities go, Chicago is a very green one since we have so many gorgeous parks. Grant Park is one of the most beautiful outdoor spaces we have. This expansive city park is home to several world-renowned festivals, including Lollapalooza and the Taste of Chicago.

Nicknamed Chicago’s Front Yard, Grant Park is also a great place to simply stroll around and take in the sights and sounds of the city. The more than 300 acres of lush landscaping and towering skyline provide a welcome respite from the hustle and bustle of downtown Chicago.

Grant Park is so large that the Museum Campus and Art Institute both reside on park property. There is so much acreage to the park that you may not even realize you’re there while you’re visiting. Just be sure you stop by to see Buckingham Fountain while you’re here, it’s a must!

39. Take a History Tour of the Wrigley Building and Tribune Tower

Wrigley Building at Night with Michigan Avenue Bridge
Tinnaporn Sathapornnanont / Shutterstock

Address: 400-410 Michigan Ave and 435 N Michigan Ave

Begin your journey at the historic Tribune Tower. Former home to The Chicago Tribune newspaper turned condos and retail space, this stunning example of Gothic architecture has long since been part of Chicago’s skyline. Built between 1923 and 1925 along the Chicago River, this monumental behemoth is only steps from the Chicago Riverwalk.

Across the street from the tower is the Wrigley Building – look for its two towers connected by an archway. Clearly from this building and Wrigley Field, you can tell that Wrigley Gum is a Chicago success story. William Wrigley Jr. started out selling soap and baking powder in 1891. But a year later, Wrigley started packaging gum as a marketing gimmick for its original products – soon, Wrigley Gum made the Wrigley family quite wealthy.

This elaborate white terra cotta building built between 1920 and 1924 once housed Wrigley headquarters. Now the building is home to various companies while the ground level houses a Walgreens, Peet’s Coffee, and a few other retail businesses as well.

40. Head North to Montrose Beach

Montrose Beach in Uptown, Chicago
James Andrews1 / Shutterstock

Address: 4400 N Lake Shore Dr, Chicago, IL 60640

Montrose Beach is located along the northern shoreline of Lake Michigan near Uptown, Chicago. This beautiful beach stretches for nearly two miles and features plenty of space for relaxing or participating in sports such as sand volleyball or soccer.

The beach also features concessions where visitors can purchase food and drinks and restrooms for convenience. Montrose Beach is a great spot for families looking to spend a day outdoors because it also includes playgrounds for kids.

Besides the recreational area of the beach, south of that part is a migratory bird refuge. This area, known as Montrose Point, is a wonderful place for bird-watching. Over 300 species of birds have been recorded as visiting the refuge. Piping Plovers are famous visitors to the area and bring tons of visitors to see them when they migrate during mating season.

See Related: Best Beaches in the US to Visit

41. Take an Architecture Cruise on the Chicago River

Chicago Architecture River Cruise

The architecture of Windy City is one-of-a-kind and truly historic. From immense Art Deco beauties to towering modern skyscrapers, Chicago has it all. Take a cruise down the Chicago River to get a unique view of some of the most famous buildings in the city. The cruise will pass by some of the city’s iconic skyscrapers, like the Willis Tower.

You’ll also get an up-close look at some of Chicago’s beautiful bridges and other architectural gems along the way. Enjoy learning about the history and stories behind these structures while you take in this incredible view from the water.

Visitors walking the Chicago Riverwalk wave as architecture river cruise boats pass by. You’ll see tons of boats on the Chicago River because there are several cruise companies in the city. You can enjoy the sights during sunset, with brunch, or just a casual no-frills history cruise.

42. Spend a Rainy Day at Garfield Park Conservatory

The interior of Garfield Park Conservatory
Nagel Photography / Shutterstock

Address: 300 N Central Park Ave, Chicago, IL 60624

Visiting Garfield Park Conservatory is a great way to spend your day. Whether you just want to take a leisurely stroll or explore the many attractions and exhibits, there’s something for everyone. This conservatory has been showcasing the wonders of flora to the public since 1908.

The botanic garden is full of lush greenery, colorful flowers, and exotic plants from around the world. The conservatory also features seasonal displays, such as the Orchid Show or holiday-themed decorations that make it a popular attraction throughout the year. It’s especially great for escaping Chicago winters.

There are plenty of activities to keep visitors entertained, such as educational programs, art exhibits, and other special events. With its unique architecture and beautiful gardens, Garfield Park Conservatory provides an unforgettable experience that no one should miss out on when visiting Chicago.

43. Enjoy an Afternoon at the Chicago Children’s Museum

Entrance to the Chicago Children's Museum

Address: 700 E Grand Ave, Chicago, IL 60611

The Chicago Children’s Museum is one of the coolest museums to visit with kids. Located at Navy Pier, the museum offers many interesting exhibits for children and adults alike. From interactive play areas to educational activities, there’s so much to explore and experience at the Chicago Children’s Museum.

Some of their fan-favorite exhibits include the climbing Cloud Buster, Play It Safe and Kids Town. There are even activities for the tiniest learners with things appropriate for babies and toddlers.

The museum also offers a range of special events throughout the year, such as family workshops and kid-friendly movie screenings. With so many things to do with kids, the Chicago Children’s Museum is sure to be a great day out for all ages.

44. Bring Your Kids to Maggie Daley Park

Aerial View of Maggie Daley Park
f11photo / Shutterstock

Address: 337 E Randolph St, Chicago, IL 60601

Maggie Daley Park is a great place to bring your kids for some outdoor activities. It is part of the larger Grant Park and has many recreational opportunities. Kids can explore the park’s unique features such as an ice-skating ribbon, a climbing wall, two playgrounds, and more.

Although there is so much for families to do together, the park is still free with no admission costs. It is open until 9 pm each day. However, guests under the age of 18 are required to be with an adult if at the park after 6 pm.

There are also plenty of picnic areas for families to utilize. The park also offers educational programs that teach about nature, science, and more. Maggie Daley Park is a great way to spend time with your family while visiting Chicago.

45. Tour the Chicago Theatre

The interior of the Chicago Theatre
Nagel Photography / Shutterstock

Address: 175 N State St, Chicago, IL 60601

The Chicago Theatre is one of the city’s most iconic landmarks and a great place to visit. Built in 1921, this historic theater is still a popular destination for locals and tourists alike looking to see a show. The original lavish movie palace set the bar for all other movie palaces that came after it.

Designed in the French Baroque style, the exterior of the Chicago Theatre features a miniature replica of Paris’ Arc de Triomphe. The interior design of the theater is also something special to experience – with its ornate ceiling, grand chandeliers, and luxurious decor, it’s easy to feel transported back in time when you step inside.

Currently, the theater still showcases some of the world’s greatest minds and talents. Its first few decades featured performers such as John Phillip Sousa, Duke Ellington, and Benny Goodman. So why not take a tour of this incredible piece of Chicago and American history?


What are some good shopping areas in Chicago?

Some of the best shopping areas in Chicago include The Magnificent Mile, State Street, Wicker Park, and Logan Square.

How do I get around Chicago?

The best way to get around Chicago is by using public transportation. The Chicago Transit Authority (CTA) operates the city’s bus and train system. You can purchase a Ventra Card, which allows you to use the CTA buses and trains, at any CTA station. If you’re planning on taking the train frequently, you may want to purchase a 7-day or 30-day pass. The Ventra app also works on card-reading terminals, so you don’t have to buy a physical pass anymore. There are even a few Chicago River ferries as well.

What are some of the most popular tourist attractions in Chicago?

Some of the most popular tourist attractions in Chicago include Millennium Park, Navy Pier, The Art Institute of Chicago, The Field Museum, and Shedd Aquarium. The Chicago Riverwalk along the downtown Chicago River is also a popular spot for photos and relaxing in the city.

What are some good places to eat in Chicago?

Some good places to eat in Chicago include Al’s Beef, Portillo’s, Giordano’s, Lou Malnati’s Pizzeria, and The Purple Pig.

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