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Chicago Travel Guide – 25 Things to do in Chicago, USA

By Two Monkeys Travel - Contributor May 13th, 2020 Posted in Central America Travel Blog, Travel Blog, Travel Guides No comments

Famed for its remarkable skyline, Chicago, is one of the largest cities in the U.S. What started as a small trading post bloomed to become a global city of international trade and commerce. It doesn’t only boast of its tall skyscrapers with great architecture but humungous parks full of art and activities and the dazzling Lake Michigan and Chicago River; Chicago is a great mix of city and nature. Chicago might be called the “Windy City,” it will feel warm as Chicago opens its arms to welcome you.

Things to do in Chicago
Photo by Pedro Lastra

With absolutely many things to do, we summed it up to the 25 things to do in Chicago to help you with your visit.

1.  Hang out at the Millennium Park

Things to do in Chicago
Photo by Lance Anderson

Millennium Park is located in the middle of the city of skyscrapers and Lake Michigan. It’s not only a park, but you can also check out an event or a free concert there. A garden is also beautiful as well as an ice rink during the winter. There’s also a bridge and a cycle center. Millennium Park is a thing to do in Boston with countless activities to choose from.

Suggested Tour: Big Bus Chicago Hop-On Hop-Off Tour

2. Have fun at the Navy Pier

Things to do in Chicago
Photo by Josh Howard

Encompassing attractions, shops, restaurants, and exhibition facilities, the Navy Pier is one of the top things to do in Chicago. It also provides a great view of Lake Michigan and downtown Chicago. The Navy Pier, especially the Ferris wheel looks excellent at night. Enjoy the day; eating, relaxing, shopping and having fun at this stop.

Suggested Tour: Signature Food Tour at Navy Pier

3. Take a picture with the Cloud Gate

Things to do in Chicago
Photo by Sawyer Bengtson

The Bean, as other’s coined it much to the artist’s dislike, is found in the Millennium Park. Cloud Gate is 33 x 66 x 42 feet and made up of 168 stainless steel plates. It was created by Sir Anish Kapoor, a British Sculptor. You can see this in films too like Transformer Series.

Suggested Tour: Food, History and Architecture Combo Tour

4. See the Museum of Science and Industry

Things to do in Chicago
Photo by Brent Payne CC BY 2.0

The MSI is the largest museum in the Western Hemisphere. It is inside the only remaining building from the World’s Fair in 1983; so it’s a must-see. From the old trains, weather to the human body;  there are over 2,000 exhibits in this museum. It has a lot of interactive exhibits too, so put your science cap on and be filled with absolute wonder.

Suggested Tour: Chicago South Side Tour with Optional River Cruise

5. Walk the Magnificent Mile

Things to do in Chicago
Photo by Teo Romera CC BY-SA 2.0

The Mag Mile is one of the world’s most magnificent avenues. It is filled with upscale department stores, top-rated hotels, world-class restaurants, and commercial buildings. With more than 400 stores, 250 restaurants and 60 hotels; you can get a one of a kind Chicago experience.

Suggested Tour: Chicago Walking Tour: The Magnificent Mile

6. Go Up the Willis Tower

Things to do in Chicago
Photo by Noel Forte on Unsplash

The Willis Tower is the 3rd tallest building in the United States. The Skydeck is on the 103rd floor of the building at 1,353 feet. You can feel the building swat and see Lake Michigan, Chicago skyline, and on a clear day the other parts of Illinois.  There are all-glass boxes where you can see the street below; so all those who are afraid of heights can conquer their fears here. This building is also featured in films like Transformers, Dark Knight and Divergent.

Suggested Tour: Skydeck Chicago Admission

7. Laugh at Second City

The Second City is an improvisational theatre troupe based in Chicago. It has been a starting point of comedians like Tina Fey, Amy Pohler, Mike Myers, Steve Carrel, and many more. Catch a show and ready yourselves for a fun-filled night.

Suggested Show: She The People at The Second City

8. See the lights at Buckingham Fountain

Things to do in Chicago
Photo by Brian Miller

One of the largest fountains in the world, Buckingham Fountain is a landmark in the center of Grant Park. It operates from April to October with color-light shows in the evening, during winters it is decorated with lights. If you want to see it in the morning, there is a show operating ever hour starting from 8:00 am. It is so big; you will be in awe.

Suggested Tour: Chicago Segway Night Tour

9. Go on an Architecture Boat tour

Things to do in Chicago
Photo by Gautam Krishnan

The city boasts of its architecture, so book a boat tour on the Chicago River.  You will see over 40 Chicago landmarks while on your seat cruising by the river. There are tour guides too who could explain the history or the style of the building. For those who visit here; it’s one of the best things to do in Chicago.

Suggested Tour: Chicago River Architecture Tour

10. Watch Sports at Chicago

Things to do in Chicago
Photo by Heather Maguire

The sports city has many sport-related clubs; Bears (Football), Cubs & White Sox (Baseball), Blackhawks (Ice Hockey), Bulls & Sky (Basketball), and Fire & Red stars (Soccer). The Wrigley Field and the United Center is a popular spot. Catch a game and cheer for the local team.

11. Appreciate Art at the Art Institute of Chicago

Things to do in Chicago
Photo by Mobilus In Mobili CC BY-SA 2.0

The Art Institute of Chicago is one of America’s oldest and largest art museums. It has about 300,000 collections of art; on Impressionism and Contemporaries. A famous art here is A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat and American Gothic by Grant Wood. You wouldn’t only appreciate the paintings too, the building’s architecture is quite beautiful.

Suggested Tour: Skip the Line Art Institute of Chicago Admission Ticket

12. Bike in Lincoln Park

Things to do in Chicago
Photo by Robert V. Ruggiero

The Lincoln Park, named after Abraham Lincoln, is a 1208-acre park along Lake Michigan. There are recreational facilities for sports ranging from baseball to archery. There are also superb gardens, artworks, museums, and a free zoo. Catch an outdoor performance during the summer.

Suggested Tour: Chicago Bike Tour

13. Eat Chicago-style Pizza

Things to do in Chicago
Photo by Jonathan J. Castellon

Pizza, especially Chicago-styled ones, should be part of your to-do list in Chicago. The deep-dish pizza has a high edge giving big space for cheese and tomato sauce. The Stuffed Pizza has surprises inside while the Thin-crust pizza is thin with a crunchy feeling. FYI: A popular topping in Chicago is sausages. There are hundreds of pizza shops in this bustling city; prepare yourself and judge which is the best.

Suggested Tour: Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour

14. See a concert at Jay Pritzker Pavilion

Things to do in Chicago
Photo by Tony Webster CC BY 2.0

The pavilion is located in Millennium Park and is home to the Grant Park Symphony Orchestra and Chorus. Try visiting when there is a Grant Park Music Festival as there is a free music concert there. If the seats are full, try sitting on the lawn and enjoy the night sky too.

15. Go inside Field Museum of Natural History

Things to do in Chicago
Photo by Heather Paul CC BY-ND 2.0

One of the world’s largest museums, The Field museum focuses on natural history. You will see fossils billions of years ago; from single-celled organisms to dinosaurs. Some scientists will show you some works and answer your questions. The museum also boasts a library with over 275,000 books and photo archives. This will be a gateway to history; check it out when you go to Chicago.

Suggested Tour: Field Museum of Natural History Admission

16. Swim at Lake Michigan

Things to do in Chicago
Photo by André Morand CC BY 2.0

Go to the beach and swim in Lake Michigan, one of the Five Great Lakes of North America. There are 24 beaches; Montrose Avenue Beach is the largest. You can also take a stroll, fish, boat or even attend a party!

17. Learn about plants in Garfield Park Conservatory

Things to do in Chicago
Photo by Ryo Chijiiwa CC BY 2.0

Garfield Park is one of the largest greenhouse conservatories in the United States; it is also known  as “landscape art under glass.” It is a hidden gem on the west side of Chicago. Enjoy walking through the striking plants, flowers, and trees and learn about them too.

Suggested Tour: Train and Walking Tour – Green Line: West Loop

18. See Chicago at John Hancock Center

Things to do in Chicago
Photo by Jonathan J. Castellon

This 1,128-foot building is located in Magnificent Mile and the 4th tallest in Chicago. On its 95th floor, there are restaurants, and you can have a 360-degree view of Chicago. The TILT is here, where you lean on a window, and it tilts to 30 degrees to see a better view of the streets. Imagine the shaky knees and the thrill of it!

Suggested Tour: 360 CHICAGO Observation Deck Admission (Hancock Center)

19. Bike along the Lakefront Trail

Things to do in Chicago
Photo by Jonathan J. Castellon

There is a 22-mile Bicycle Trail in Chicago; so find a shop to rent a bike. The trail passes by popular parks like the Millennium, Lincoln and Grant Parks. It is a great way to see Chicago; it’s environment-friendly, an excellent form of exercise, saves you transportation money, you can have your own schedule and avoid traffic too.

Suggested Tour: Chicago’s Greatest Hits Bicycle Tour

20. Check out the Chicago Theatre

Things to do in Chicago
Photo by Sawyer Bengtson

Built in 1921, the theatre was initially known as Balaban and Katz Chicago Theatre. It is famous as the “CHICAGO” sign is featured frequently in films and artwork. When there’s no show, check out the interior as it shows French Baroque influence. It looks small on the outside but is seven stories tall and fills half a block.

Suggested Tour: Chicago Theatre Marquee Behind-the-Scenes Tour

21. See the Stars at Adler Planetarium

Things to do in Chicago
Photo by looneytuneted CC BY 2.0

Adler Planetarium & Astronomy Museum founded in 1930 was the first planetarium in the US. Explores space and discover the museum through the Adler. Get to see the sun through Doane Observatory. The building architecture is quite exciting and a great view of the Chicago Skyline.

Suggested Tour: Adler Planetarium

22. Stroll along Old Town

Old Town is home to Victorian-era buildings in Northside Chicago. You can appreciate the architecture of some buildings including a Fachwerk-style building. St. Michael’s Church is also located here; it is one of the buildings that survived during the Great Chicago Fire in 1871.

Suggested Tour: Chicago Crime and Mob Tour

23. Hang out at the Wicker Park

Things to do in Chicago
Photo by Nitram242 CC BY 2.0

Find the art community, food scene, hipster culture and nightlife at Wicker Park. This is a neighborhood in the West Town of Chicago. Check out bands, gourmet-restaurants, high fashion boutiques and artsy business here.

Suggested Tour: Chicago Prohibition Tour

24. Attend Mass at Holy Name Cathedral

Things to do in Chicago
Photo by Jason Raia CC BY 2.0

The Seat of the Archdiocese of Chicago is at Holy Name Cathedral. The church was built with a Gothic style of architecture and is 233 feet tall. Appreciate the extraordinary woodwork as well as the stained glass windows. You will be lucky to hear the pipe organs playing; they are pleasant to the ears.

Suggested Tour: Big Bus Chicago Hop-On Hop-Off Tour

25. Get wet at Crown Fountain

Things to do in Chicago
Photo by Matthew T Rader

Crown Fountain is an interactive work of art in Millennium Park. The water operates from May to October, and through LED Lights, you can see diverse faces like spouting water. At night, solid colors are displayed, and people play with their silhouettes. Water also cascades so typically, people who want to get wet play there.

Suggested Tour: 2 HR History of Chicago Architecture & Art Segway Tour

26. Find accommodation in Chicago, United States

Frequently Asked Questions

1. Is it safe to travel to Chicago?

Chicago is relatively safe; generally safe for tourists. Practice caution and avoid isolated areas Chicago’s North Side is recommended. Stay in touristy and well-lit areas at night; avoid walking alone. However, in case of emergencies, dial 911.

2. Should I get travel insurance before heading to Chicago?

I always recommend buying travel insurance since we don’t know what will happen to us. Check out SafetyWing, my insurance provider.

3. Is it expensive in Chicago for tourists?

Chicago is a bit expensive but not as expensive as New York. To stick on a budget, try staying at a hotel near tourist spots to avoid transportation costs and do free things.

4. When is the best time to visit Chicago?

The best time to visit Chicago is from May to June (for Spring) and September to October (for fall) with great temperature. July is the hottest month, but winter is also a great time; however since it’s the “Windy City”, the wind will feel ice cold.

4. Where should I stay in Chicago?

You can stay at Downtown Chicago for the Loop, River North or Michigan Avenue (Mag Mile.)

5. What souvenirs should I buy in Chicago?

Try buying a building replica, a snow globe with Chicago Skyline or the bean-shaped pendant.

6. How to get to Chicago?

There is O’Hare International Airport in Chicago’s Northwest Side. It has non-stop flights to 228 destinations in North America, South America, Africa, Asia, Europe, and Oceania.

7. How to get around Chicago?

You can easily navigate Chicago by walking, public transportation (buses or trains) or taxi. A cheaper and healthier way is through biking.

We hope you have fun on your trip to Chicago and enjoy this list of 25 things to do in Chicago.

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Written by Two Monkeys Travel - Contributor

Two Monkeys Travel Group – Community Travel Blog is a travel blog and website. We quickly grew into a valuable source of inspiring travel stories, advice, itineraries and travel guides, with the aim of demonstrating how to live a sustainable life of travel, whilst living your own definition of success. If you'd like to contribute and write a guest post, contact us at [email protected]