Select Page

52 Best Things to do in Chicago

Illinois

As one of the truly great cities in the United States, Chicago stands tall as the cultural hub of the Midwest with plenty to do and see. Bordering Lake Michigan, Chicago’s waterfront location gives it a dramatic feel and the weather blowing in from the lake has given it the nickname “Windy City”. With so many great public recreation spaces like the artistic Millennium Park, the interactive Navy Pier, and the attractions in Lincoln Park. There are also a plethora of world-class museums including the Field Museum, and the Art Institute of Chicago. There is truly something for everyone here in the “Windy City”. Check out our guide to the best things to do in Chicago and get inspired to plan your next trip to Chicago.

If you are visiting with children, you’ll be glad to know that there are a variety of fun things to in Chicago with kids, like visiting the underwater magic of the Shedd Aquarium, seeing the amazing animals at the Brookfield Zoo, or playing in the imaginative kid’s structures in Maggie Daley Park. If you are visiting Chicago on a budget, then check out our guide to the top 27 Free Things to Do in Chicago.

Millennium Park
By John Lupu

1. Millennium Park

Millennium Park is quickly vying to become Chicago’s number one destination for tourists and it’s easy to see why. As part of the larger Grant Park, this special park is near the Lake Michigan shoreline and covers over 25 acres. Millennium Park is best known for its massive outdoor art installations that are spread throughout the park’s various themed sections of Cloud Gate, Jay Pritzker Pavilion, and the Crown Fountain among others.

When the weather is nice, this is a fantastic park to enjoy the scenery and appreciate the amazing art. As the centerpiece of the park, the Jay Pritzker Pavilion is a massive outdoor theater that can hold more than 7,000 people and is the best outdoor concert venue in Chicago. Don’t miss out on all the things to see and do here in Millenial Park – it’s at the top of our list of best things to do in Chicago.

Chicago Bean
By f11photo

2. Chicago Bean (Cloud Gate)

The Chicago Bean is a nickname given to the famous Cloud Gate sculpture that can be seen in Millennium Park. It’s actually one of the most photographed pieces of public art in the world and you too can snap a selfie in front of this mesmerizing sculpture. Designed by Chicago artist, Sir Anish Kapoor, this sculpture was designed to resemble liquid mercury and from a distance, it does indeed look like molten metal.

It’s fun to walk around the Chicago Bean to see your reflection change and warp depending on what side of the sculpture you’re standing on. It’s truly an amazing and unique piece of art and well worth a visit, especially if you’re already exploring Millennium Park.

Navy Pier
By f11photo

3. Navy Pier

If you want to experience Chicago’s most visited destination, then you’ll want to make your way down to the Navy Pier. This huge pier is bustling with activity and covers over 50 acres of space out over Lake Michigan. The Navy Pier is packed with fun for the whole family with amusement rides, gardens, parks, restaurants, shops, event spaces and so much more.

Originally built in 1916, the Navy Pier was originally called the Municipal Pier and used as a traditional loading spot that managed freight and passenger boat traffic, and through the years it has developed into more of a multi-dimensional entertainment and cultural center of Chicago. We think this is one of the top things to do in Chicago with kids and offers something for the whole family!

Skydeck Chicago
Courtesy of Wikipedia

4. Skydeck Chicago

Ready to test your fear of heights? The Chicago Skydeck offers a thrilling way to test your tolerance for high places with a glass floor balcony that juts out from the 103rd floor of the Willis Tower in downtown Chicago. The Skydeck was originally opened in 1974 and gives visitors incredible views of the city and on clear days you can even see locations far away in Indiana, Michigan, and Wisconsin. Another factor that can make the Skydeck an unforgettable experience is that you can feel the entire Willis Tower swaying on windy days, and giving a new dimension to the whole experience. We think Skydeck is a must-see destination and one of our favorite things to do in Chicago.

Shedd Aquarium
By James Kirkikis

5. Shedd Aquarium

For an incredible thing to do in Chicago with kids, you can explore the sprawling Shedd Aquarium. This massive facility features over 32,000 animals in tanks holding over 5,000,000 gallons of water. When it first opened in 1930, the Shedd Aquarium was the largest indoor aquarium in the whole world and is impressively large. The aquarium is a favorite spot for locals as well as tourists, and sees over 2 million visitors per year.

Of the permanent exhibits, some of the most popular permanent exhibits are the Wild Reef exhibit which features a 400,000-gallon tank holding many species of sharks and rays, and the Oceanarium – a 2,000,000 gallon tank that features beluga whales, dolphins, otters, and penguins. There are many more permanent and rotating exhibits throughout the aquarium and we think you’ll have a great time exploring this beloved Chicago aquarium.

Magnificent Mile
By Tupungato

6. Magnificent Mile

For an upscale shopping and dining experience, you can stroll Chicago’s famous Magnificent Mile near downtown Chicago. The Magnificent Mile is an upscale section of Michigan Avenue and features some of the most swanky retail stores and restaurants and has been compared to other famous shopping destinations, like Rodeo Drive in Beverly Hills, or 5th Avenue in New York. There are also many famous hotels and buildings lining the Magnificent Mile, and even if you won’t be shopping here, it’s worth walking this fancy district just to experience Chicago’s main luxury district. There are also typically interesting street performers showing off their unusual skills and this makes for an entertaining stroll along one of Chicago’s most famous streets.

Willis Tower
By Rudy Balasko

7. Willis Tower

Towering above the Chicago skyline, the Willis Tower (Also known as the Sears Tower) is one of the most impressive man-made structures in all of North America. Standing at 1,450 feet tall, this incredible office building features 110 floors of office, retail, and event space and when it was completed in 1973, it held the title for the tallest building in the world for over 24 years. A visit to Chicago would not be complete without experiencing the view from the top of the Willis Tower – The best way to do this is by walking out on the glass observation lookout at Skydeck Chicago on the 103rd floor. The Willis Tower is one of our favorite buildings to experience we think it earns the right as one of the top thing to do in Chicago during your visit.

Lincoln Park Zoo
By Matthew J Davis

8. Lincoln Park Zoo

Another fantastic thing to do in Chicago with kids, the Lincoln Park Zoo offers an amazing zoo experience that you and your kids will absolutely love. Being one of the oldest zoos in America, it is also free to visit, making it one of the few major zoos in the United States that doesn’t charge an admission fee. The Zoo houses over 1,100 different animals including zoo favorites like penguins, gorillas, monkeys, lions, and polar bears. The zoo also has some rare animals, like the endangered pygmy hippopotamus, and the West African Dwarf Crocodile. We think you’ll agree that the Lincoln Park Zoo as one of the absolute best free things to do in Chicago.

Grant Park
By Tomas Kulaja

9. Grant Park

Affectionately known as “Chicago’s front yard”, Grant Park is an epic urban park and a breath of fresh air in the heart of bustling downtown Chicago. This truly massive park features many themed areas, event spaces, and gardens across its huge 319-acre footprint. Inside Grant Park, you can visit the famous Millennium Park art installations, stroll through the beautifully landscaped Maggie Daley Park, witness the water fountain show at the Buckingham Fountain, among many other activities and destinations you can enjoy within the park. There are so many things to do and see here at Grant Park, it would truly take days to explore it all, and that’s why Grant Park is a top outdoor thing to do in Chicago in summer, spring and fall months.

Lake Michigan Cruise
By Vladislav Gajic

10. Lake Michigan Cruise

For a unique experience in Chicago, we’d recommend that you look into a Lake Michigan cruise during your visit. There are many different types of cruises you can book, like a short day cruise that gives you awesome views of the Chicago harbor and skyline, or for a romantic thing to do in Chicago, you can check out a Lake Michigan dinner cruise where you can see the Sunset over the city from the water. No matter what type of cruise you do, they all offer a relaxing way to experience Chicago and Lake Michigan, and we’d highly recommend booking some sort of cruise during your visit. It’s just such a great way to see Chicago from a unique perspective.

Adler Planetarium
By f11photo

11. Adler Planetarium

For another fun thing to do in Chicago with kids, you can visit the Adler Planetarium. This unique facility opened to the public in 1930 and features many different themed areas, such as the Space Visualization Laboratory that showcases many interactive astronomy exhibits. Another area is the Webster Institute for the History of Astronomy, which features a massive collection of science-related artifacts, instruments, artwork, and more to promote the preservation of the science of Astronomy and is one of the largest astronomy artifact collections in the world. For a fun thing to do in Chicago at Night, you can check out “Adler After Dark” – a 21+ event that happens throughout the month, where you can have a more “adult” experience of the planetarium with drinks and food and nighttime exhibits and entertainment.

Buckingham Fountain
By Vlad G

12. Buckingham Fountain

Located in the very heart of Grant Park, the Buckingham Fountain is one of the main attractions in the park and mesmerizing to watch. With the fountain water show starting every 20 minutes, you can see the fountain in action – with a timed water show that’s a truly relaxing experience. This huge fountain was dedicated way back in 1927 and holds a staggering 1,500,000 gallons of water. Since the park is open all day and into the night, you can see the fountain water show from April to October, and the fountain can be experienced from 8 am to 11 pm at night. If you watch the show at night, the water is lit up with colored lights to go along with the water display, and we think that watching the show at night is the best way to experience of Buckingham Fountain.

Lurie Garden
By Thomas Barrat

13. Lurie Garden

Lurie Garden is a beautifully crafted garden that’s a great place to relax and maybe even enjoy a picnic on a warm day. This exquisite garden is located in the Millennium Park and actually is a “rooftop garden” as it sits on the roof of the Lakefront Millennium Parking Garage below. Lurie Garden is split into 2 sides, with one side featuring thousands of colorful blooming flowers and the other side features flowers and plants under the shade of the surrounding shade trees. There is also a running stream that flows through the center of the garden and borders the wooden boardwalk that takes visitors through the heart of the garden. This garden is yet another great reason to visit Chicago’s famous Millennium Park.

Field Museum
By Jim Lambert

14. Field Museum

If you want to visit one of the premier natural history museums in North America, you can visit Chicago’s Field Museum. This massive museum is home to one of the most wide-ranging collections of complete dinosaur specimens, including the world’s largest and most complete Tyrannosaurus skeleton affectionately named “Sue”. With many great permanent exhibits, such as “Evolving Planet”, “Inside Ancient Egypt”, and “The Ancient Americas”, The Field museum offers an entertaining and educational experience that’s unmatched and that’s why the Field Museum sees over 2 million visitors each year. Learn more about the exhibits and schedule at the Field Museum website.

Chicago Deep Dish Pizza
By KameronA

15. Chicago Deep Dish Pizza

No visit to Chicago would be complete without indulging in one of this great city’s best inventions – Deep Dish Pizza. The pizza that you can find here in Chicago is unlike any other pizza you’ve tried with layer upon layer of cheese, sauce and other toppings, this legendary style of pizza is a decadent and distant cousin from what you normally think of when you order Pizza. These pizza slices are so thick that you typically don’t need much more than a single slice to be completely full. With multiple Chicago deep dish pizza shops vying for the top spot on the Chicago Deep Dish Pizza hierarchy, we’ll try to give a solid list of places to visit during your stay. One of the most classic deep dish spots is Giordanos – well known for their incredibly deep pizza pies. Other popular spots include The Art of Pizza, and Nancy’s Pizza among many others.

The Art Institute of Chicago
By AnjelikaGr

16. The Art Institute of Chicago

If you want to check out Chicago’s most cutting-edge art museum, you need to visit The Art Institute of Chicago. Located within Grant Park, this huge museum features over 300,000 rare and iconic works of art spread out within many permanent exhibits. This collection of art showcases pieces from all around the world and from a wide range of time periods, from early Japanese masters to contemporary American art icons. We’d recommend visiting this special museum if you are an art lover or are just visiting Grant Park and want to experience all that the park has to offer. See more about the exhibits and ticket information at The Art Institute of Chicago website

Oak Street Beach
By Thomas Barrat

17. Oak Street Beach

Oak Street Beach is considered one of Chicago’s best man-made beaches and is located right on the edge of downtown Chicago. This beach is a great place to relax, and enjoy the water and it can get very crowded on warm summer days. You’ll find people playing volleyball at the official volleyball courts, and you can order some food at the beachside restaurants. For a great thing to do in Chicago in the summer months, we think an afternoon at Oak Street Beach is a great option and should be near the top of your sunny day list.

Museum of Science and Industry
By ImagineerInc

18. Museum of Science and Industry

For another great thing to do in Chicago with kids, the Museum of Science and Industry is an awesome place to visit any time of the year. This huge facility is located in a historic and beautiful building that originally was home to the “Palace of Fine Arts” and is full of interesting exhibits that kids will love.

The museum features a wide variety of exhibits that will fascinate the imagination, like a full-size German submarine, a massive and detailed model train set that recreates the old city of Chicago, the first diesel-powered stainless steel passenger train, and even a full-scale replica of a coal mine. These are just a few of the fun and educational exhibits found in this incredible museum. Don’t miss the opportunity to take your kids to the Chicago Museum of Science and Industry – We know they’ll love it!

Wrigley Field
By Christopher Penler

19. Wrigley Field

To enjoy one of Chicago’s finest sporting event venues, you need to catch a Chicago Cubs baseball game at Wrigley Field. This beloved baseball stadium is located just north of downtown Chicago and can hold a crowd of over 41,000 fans. Wrigley Field is one of the most iconic and well-known baseball stadiums in the United States and has become synonymous with the deep heritage of American Baseball. We think a visit to Chicago is incomplete without trying to see a Cubs game while you’re there.

Lincoln Park Conservatory
Courtesy of Wikipedia

20. Lincoln Park Conservatory

The Lincoln Park Conservatory is a great place to visit and also an unusual thing to do in Chicago for a few reasons. The main conservatory building is a unique Victorian-style glasshouse that was built in the late 1800s and has multiple themed garden rooms for showcasing beautiful and rare plants and flowers. Surrounding the building are other gardens as well as many sculptures throughout the Lincoln Park Conservatory grounds. If you are thinking about visiting the Lincoln Park Zoo, you should also make plans to stop by this unique conservatory – it’s well worth spending an hour or two walking the peaceful grounds.

Chicago Riverwalk
By welcomia

21. Chicago Riverwalk

A really fun thing to do while you’re in Chicago is exploring the Chicago Riverfront – Also known as Chicago’s “Second Waterfront”. This winding path follows along the downtown portion of the Chicago River and has been built up over time to include shops, boat facilities, gardens, and parks. For a fun and unique way to experience Chicago, walking the Chicago Riverfront is among the top ways to see the city and explore downtown.

Chicago Water Tower
By City of Chicago

22. Chicago Water Tower

The Chicago Water Tower is an iconic building in Downtown Chicago that served as a water-pumping station to pull water in from Lake Michigan. The building has survived many city catastrophes including the great Chicago Fire and now serves as an art gallery for historic photographs and films from local Chicago artists that are now on display. If you want to see what the historic city of Chicago was like throughout the years, you’ll want to explore this special museum that now lives in the historic Chicago Water Tower.

Crown Fountain, Chicago
By Sharkshock

23. Crown Fountain

For another unusual thing to do in Chicago – you can visit the famous Crown Fountain. This public art piece is located in Millennium Park and features two 50-foot towers that project digital images onto their sides to create interesting visual expressions. Also, since this is a fountain, it’s a fun place for kids to splash around in the shallow water between the towers. While Chicago seems to be full of public art installations, we have to say that Crown fountain is one of our favorites given its unique and imaginative design. If you’re going to be visiting Millennium Park, don’t miss out on this special fountain.

Frank Lloyd Wright Home and Studio
By littlenySTOCK

24. Frank Lloyd Wright Home and Studio

For all you architecture nerds, the Frank Lloyd Wright Home and Studio in Chicago is a special destination. This is the home that the famous architect Frank Lloyd Wright built and raised his 6 children in. The house has now become a historical landmark on the National Register of Historic Places and has been lovingly restored to its original condition. The house is quite interesting architecturally and shows many of Frank Lloyd Wright’s famous design elements and also displays many sculptures on the exterior that were designed by Frank’s collaborator, Richard Boch. This home is worth a visit if you appreciate modern architecture and especially if you are a fan of Frank Lloyd Wright’s work.

Jay Pritzker Pavilion
Deatonphotos / Shutterstock

25. Jay Pritzker Pavilion

The Jay Pritzker Pavilion is a massive outdoor concert and event space located in the heart of Millennium Park and features many concerts, events, and shows throughout the year. The design of the Jay Pritzker Pavilion is very unique and was designed by the famous architect Frank Gehry and opened in 2004. The stage area of the pavilion is designed out of a mesmerizing & flowing walls of metal that are meant to project the sound from the stage out over the audience. There is fixed concert seating for 4,000 people in the pavilion and beyond that there is a grass amphitheater that can hold 7,000, making this venue able to hold over 11,000 people at maximum capacity. It is a real treat to see a concert at this special venue, so be sure to review the Jay Pritzker Pavilion event calendar to see what’s playing during your visit.

Maggie Daley Park
Courtesy of Wikipedia

26. Maggie Daley Park

If you are looking for a park that has it all, you might want to visit the extraordinary Maggie Daley Park. This 20-acre park in Chicago’s greater Grant Park is fun for the whole family and a great thing to do in Chicago with kids. Maggie Daley Park was first opened in 2014 and has tennis courts, picnic lawns, themed gardens, huge play areas for kids, Ice skating rink, and rock climbing walls, and so much more. If you are looking for a park that can keep your kids busy all, day, we think Maggie Daley Park is your best option.

Museum of Contemporary Art
4kclips / Shutterstock.com

27. Museum of Contemporary Art

If you looking for a unique and unusual art experience, you can visit the Chicago Museum of Contemporary Art. This museum is located in the heart of downtown and features a massive collection of post-World War 2 visual art in many styles such as surrealism, minimalist, and conceptual art among many other styles. The exhibits are mainly temporary with new exhibits rotating through the museum. If you are a fan of modern art or are just looking for an unusual thing to do in Chicago, we think you’ll be entertained and challenged in your conception of art by visiting this special museum.

Lakefront Trail
JW_PNW / Shutterstock.com

28. Lakefront Trail

If you are wanting to get out for some exercise, then the Lakefront Trail should be high on your list of destinations. This nearly 20-mile-long pathway snakes along the western Lake Michigan shore, connecting many of the lakefront parks, beaches, and waterfront recreation areas. It’s a popular spot for bicycling, running, skateboarding, and walking, and it can get crowded on warm summer days. On some extra busy days, this trail is known to see over 70,000 visitors. For a great way to see the city and to get some exercise, we’d highly recommend you enjoy the scenery from the popular Lakefront Trail.

North Avenue Beach
elesi / Shutterstock.com

29. North Avenue Beach

For another popular beach destination in Chicago, you can enjoy the sun, sand and water from the North Avenue Beach. This broad beach is located right next to downtown and also right next door from Oak Street Beach. Many consider this the top beach in Chicago due to its abundance of sand and also because it has the largest lifeguard staff. North Avenue Beach hosts a large international volleyball tournaments each year and you will often find serious volleyball matches in progress on most sunny afternoons. This beach can also get quite crowded on warm summer days, so be prepared to get there early to lock in your spot on the sand.

The Bloomingdale Trail
Carlos Yudica / Shutterstock.com

30. The Bloomingdale Trail

The Bloomingdale Trail is an interesting path to visit in Chicago as it is built on top of a reclaimed raised railway. The city of Chicago decided to turn on old raised train line called the Bloomingdale Rail Line into a community path and “greenway” that could be enjoyed as a unique recreational destination. The trail fully opened to the public in 2015 and is 2.7 miles long and features a paved pathway and landscaped areas along the trail. The Bloomingdale is now enjoyed by joggers, bike riders, and is loved by the residents that live in the surrounding neighborhoods and is a fun path to experience as you are up high above the city streets below.

Chicago River Tour
Con Katz / Shutterstock.com

31. Chicago River Tour

One great way to experience downtown Chicago is to enjoy a fun Chicago River cruise. Since the Chicago river runs through the heart of Downtown, experience the city by boat is actually a great way to get to know the city. There are many different themed cruises you can book, like a Chicago River Dinner cruise, a Chicago River Architecture Tour, or even a speedboat tour of the Chicago River. We’d recommend looking into some sort of river tour and we think that Wendella offers some of the best Chicago River tours available so check out their website for more details.

Northerly Island
By James Andrews1

32. Northerly Island

Northerly Island is a manmade peninsula that juts out into Lake Michigan and is the home to the Adler Planetarium, a concert venue, and a winding system of pathways throughout the open nature areas. With a lagoon in the center of the island, visitors can often see many types of birds, butterflies, and other wildlife while walking the miles of pathways that traverse this 90-acre island. Northerly Island pathways are open at night until 11 pm and walking the trails here is a fun thing to do in Chicago at night, but make sure you bring a flashlight as these paths aren’t lit.

Michigan Avenue Bridge
By Mark Baldwin

33. Michigan Avenue Bridge

This unique and iconic bridge was important to the expansion of the city of Chicago. The Michigan Avenue Bridge was the link that finally connected North and South Chicago together on one straight boulevard through the heart of the city. The design of the bridge is interesting for a few reasons. First, it is a bridge that is built in two pieces so that it can lift up to let tall boats through – and it does this twice per week in the spring and fall. Second, this bridge is built with 2 separate levels – a double-deck bridge that lets faster traffic go on the top level and slower commercial traffic travel on the bottom level.

It is thought that this is the first bridge of this kind to ever be constructed to have vehicle traffic on both levels. To learn more about this amazing bridge you can visit the McCormick Bridgehouse which sits on the south side of the bridge and is now a museum that celebrates the history and design of the Michigan Avenue Bridge.

Chicago Food Tours
By Chicago Food Planet

34. Chicago Food Tours

For another fun and unusual thing to do in Chicago, you can go on one of the many themed Chicago Food Tours that are offered by many different tour companies. Tours ranging from the serious to even wacky – with titles like “Underground Donut Tour“, to “Chicago Beer Experience” Tours, to a “Bikes Bites and Brews“, to even a chef-led “Chef Driven Food Tours“. It seems there is no end of creative tours you can take of the rich Chicago culinary scene and we think this is one of the best and most enjoyable ways to experience the Windy City. So, after reviewing what’s out there, book your very own Chicago food tour and eat and drink your way around town!

BP Pedestrian Bridge
By Devon Neff

35. BP Pedestrian Bridge

The BP Pedestrian Bridge, or BP Bridge for short, is an interesting snakelike curving pedestrian bridge that crosses over Columbus Drive and connects visitors between Millennium Park and Maggie Daley Park. The bridge is constructed out of stainless-steel plates for the outside shell, and the walkway itself is made from Brizillion hardwood boards, so its a bridge that feels more like a beach boardwalk. With its unique design, it is truly half public art-piece and part bridge and well worth a visit if you are exploring one of the surrounding parks. We think the BP Pedestrian Bridge is actually one of the highlights of the downtown parks and should definitely be on your Chicago itinerary.

Oz Park
By James Andrews1

36. Oz Park

OZ Park is a sprawling and fun park in the North Chicago Lincoln Park neighborhood that has many great features for kids. Among the many features, this park is “Wizard of OZ” themed and showcases many statues of characters from the movie, like the Tin Man, Cowardly Lion, Scarecrow, and of course, Dorothy and Toto throughout the park grounds. Oz Park features large play areas for kids, a winding walking path, and athletic courts for basketball, volleyball, and tennis. If you are visiting or staying in or around the Lincoln Park neighborhood and you have kids, then OZ Park is a must-see and another fun thing to do in Chicago with Kids.

Maggie Daley Park ice skating ribbon
Courtesy Of Wikipedia

37. Maggie Daley Park Ice Skating Ribbon

For a fantastic outdoor experience in the wintertime, we suggest you visit the Maggie Daley Park Ice Skating Ribbon in Maggie Daley Park. This outdoor ice path winds through the park and is one quarter-mile long and gives you the impression that you are ice skating on a river. And if you are visiting Chicago in the summer, you can still enjoy this part of the Maggie Daley park as it is converted into a rollerblade and roller-skating path for warmer weather enjoyment. We think the Maggie Daley Park Ice Skating Ribbon is one of the most unique and fun features of the greater Grant Park area and we think you’ll love it too.

Chicago Sports Museum
Courtesy of Wikipedia

38. Chicago Sports Museum

Even if you aren’t a sports fan, we think that the Chicago Sports Museum is at the top of the list of Chicago’s best museums. This destination is much more than a stuffy museum, it’s an interactive, high-tech experience where you can experience sports and test your skills like never before. You can test your hockey scoring skills alongside Chicago’s great hockey players, or shoot hoops with Chicago Bull’s team members, or even test your racecar-driving skills on the Chicago Speedway! In addition to all the interactive exhibits, there are thousands of artifacts and memorabilia from famous events and players. Don’t miss this special museum during your visit.

Humboldt Park
Thomas Barrat / Shutterstock.com

39. Humboldt Park

Humboldt Park is an interesting park on Chicago’s west side that is known for its interesting architectural, and natural features. Spread out over nearly 200 acres, Humboldt Park has many interesting and fun areas to explore. There are many great areas of this park, including recreation facilities for various sports, an inland beach at one of the manmade lakes, flower gardens, famous bronze sculptures, and multiple large playground areas for kids throughout the park. Also, there are multiple historic buildings on the property include the famous Boathouse Pavilion and the Humboldt Park Stables to new a couple. We think this is one of the great historic parks of Chicago and it’s a great place to explore during your visit.

American Writers Museum
Courtesy of American Writers Museum

40. American Writers Museum

For another unusual museum to visit, you can check ou the American Writers Museum – a museum that celebrates Americal literature. This museum was opened in 2017 and features many exhibits that educate the visitor on the writing tradition and focus on different aspects of the creative writing process. In addition to exhibits like “Word Waterfall”, “Chicago: A City of Writers”, “Surprise Bookshelf”, and “American Voices” among others, there are also interactive areas for kids that will inspire a new generation of writers. We think that a visit to the American Writers Museum is a great option for writing fans, or if you are just looking for unusual things to do in Chicago.

Logan Arcade
Credit: Sean Rioux

41. Logan Arcade

For an entertaining thing to do, you can visit the Logan Arcade to play their incredible collection of pinball machines and other vintage video games. It’s not every day that you get to play these mechanical games in our increasingly digital world and that gives this arcade a certain nostalgic charm and atmosphere. Logan arcade does serve alcohol, making this a 21+ venue, so be sure to plan accordingly. We definitely love the Logan arcade and it’s near the top of our list of unusual things to do in Chicago.

42. Centennial Wheel

If you are visiting the Navy Pier in Chicago, then you need to take a ride on the gigantic Centennial Wheel. This massive Ferris wheel features inclosed glass gondolas that allow you to take in amazing views of the Chicago skyline and at the peak, you are sitting 200 feet in the air. We think riding the Centennial Wheel is a great thing to do in Chicago at night to see all the city lights and also one of the more romantic things to do in Chicago. So, if you are visiting the Navy Pier area, head on over to the giant Ferris Wheel to enjoy the views.

Chicago Theatre
Songquan Deng / Shutterstock.com

43. Chicago Theatre

If you want to visit Chicago’s most historic and theatre, then head on over to The Chicago Theater. This iconic theater is located in the Loop district of Chicago and was originally opened way back in 1921. It was a big hit with Chicago residents and became the main theater operation in Chicago for many years. It eventually fell into decline until recent ownership changes have brought it back as one of Chicago’s main destinations for world-class stage performances, magic shows, stand up comedy, and music concerts among many other events that are now held here. For an authentic Chicago night at the theater, we can think of no better place to see a show than the acclaimed Chicago Theater.

Alfred Caldwell Lily Pool
By James Andrews1

44. Alfred Caldwell Lily Pool

For an interesting thing to visit within Lincoln Park, you can check ou the Alfred Caldwell Lily Pool. This peaceful pond is a great place to sit and relax and watch the wildlife gathering all around you. Visitors can see chipmunks, butterflies, turtles, and singing birds in their natural habitat around the pond. As it’s such a picturesque location in Lincoln Park, you can also often see photographers here doing photo shoots with couples or families. We think this a great stop on your tour of Lincoln Park, so don’t miss the opportunity to relax and enjoy nature at the Alfred Caldwell Lily Pool.

Chicago Pedway
By Don Harder

45. Chicago Pedway

Like other cities in the colder regions of North America, the winter weather in Chicago can be blisteringly cold and the streets nearly impossible to navigate during the common winter storms. That’s where the Chicago Pedway comes in. The Chicago Pedway is a massive system of underground tunnels, enclosed bridges, and shopping areas that connect a majority of Chicago’s downtown business district and enables workers and visitors to connect between subways and most of the buildings around downtown without facing the weather. Visiting the Chicago Pedway is a fun way to travel around downtown in the wintertime. Learn more about the Chicago Pedway here.

Chinatown Chicago
Kristopher Kettner / Shutterstock.com

46. Chinatown

For a taste of China right in the middle of Chicago, you can stroll the foreign streets of Chicago’s Chinatown district. As Chicago was one of the first and largest settlement of Chinese immigrants in the United States, it is no wonder that it now is home to nearly 100,000 Chinese people to this day. Walking the streets of Chinatown makes you feel as if you’ve transported halfway around the world, with authentic Chinese shops, restaurants, boutiques, and grocery stores lining the streets. We think a trip to Chinatown in Chicago is a great cultural experience for anyone and a fun place to visit especially if you enjoy authentic Chinese food.

Brookfield Zoo
Joe Hendrickson / Shutterstock.com

47. Brookfield Zoo

For another zoo option in Chicago, you can visit the Brookfield Zoo. This zoo is located to the west of Chicago in the suburbs and covers a massive 216 acres and features over 2,300 animals throughout the thoughtfully designed grounds. Some of the highlights of the Brookfield Zoo are its indoor dolphin show and exhibit and the fantastic indoor rain forest where you feel completely transported to a tropical jungle. With so many animals parklike atmosphere, we know that the Brookfield Zoo is a top thing to do in Chicago with kids. You can learn more about hours and tickets and the Brookfield Zoo website.

Taste of Chicago Festival
By ChooseChicago

48. Taste of Chicago Festival

To see what it’s like to visit the world’s largest food festival, you can explore the Taste of Chicago – a yearly 5-day festival held in Grand Park in early July. This tasty festival showcases the broad variety of foods found in the Chicago food scene as well as features cooking shows and demonstrations, art exhibits, concerts, and play areas for kids. To go along with all the great food, there are also top music artists on hand to provide entertainment throughout the festival. Another great thing about this festival is that it’s absolutely free, and so we vote this as one of the top free things to do in Chicago if you are visiting during July.

Chicago Jazz Festival
Courtesy of Wikipedia

49. Chicago Jazz Festival

Another great free thing to do in Chicago, the Chicago Jazz Festival is a popular 4-day event that’s held in Millennium Park. This festival showcases many internationally famous jazz icons and talented local jazz artists and you can hear many different types of jazz music on various stages throughout the park. Thousands of jazz fans come from around the world to experience this immersive celebration of jazz and you can too, for free! The Chicago Jazz Festival is another reason why Chicago has become a cultural center of the midwest.

Chicago Shakespeare Theater
By Chicago Shakespeare Theater

50. Chicago Shakespeare Theater

For yet another reason why you should visit the Navy Pier, you can see incredible stage performances at the Chicago Shakespeare Theater. This renowned theater on the pier has weekly performances of its own Shakespeare play series and gives over 600 performances each year. The theater is actually a complex of multiple theaters of varying sizes used for different types of performances. You can learn more about upcoming performances and events at the Chicago Shakespeare Theater website.

Related Travel Guides

14 Best Things to do in Springfield IL

A city where President Abraham Lincoln practiced law and met his wife, Springfield, Illinois, is a perfect place to visit for both nature lovers and history buffs. With a population of about 100,000 residents, this small state capital is home to many interesting...

17 Best Things to do in Chicago at Night

While there is so much to explore in Chicago during the day, there are just as many great things to do in Chicago at night. You can visit Millennium Park and the Giant Chicago Bean sculpture surrounded by the city lights, or you can see a Cubs game at the famous...

26 Things to do in Chicago With Kids

If you're bringing your kids to Chicago, then you'll be happy to know that there are some truly amazing things to do in Chicago with kids - and many of them are free. For example, you can visit the sprawling themed play structures in Maggie Daley Park, or explore the...

27 Free Things to do in Chicago

If you are visiting Chicago and are looking for some great ways to see the city on a budget, then we've got a great list for you. Check out the top free things to do in Chicago - Things like snapping a selfie at the famous Chicago Bean sculpture, or seeing all the...

Other Travel Guides