Welcome to Chicago! I’ve found this city countless times, and it never gets old. Last year, more than 55.3 million people visited. The guide describes the core attractions but also covers the special attractions of Millennium Park and deep-dish pizza places that put Chicago on the culinary map. Chicago has wonderful artwork, huge skyscrapers, and vibrant neighborhoods. So, what are the top things to do in Chicago? You will get a sense of how to map out a memorable trip. There is so much life and history in the city, and I can’t wait to share my favorite places.
| Travel insurance– Absolutely necessary for any trip. It’s nice to be able to make a trip without worrying about any unexpected expenses. |
Things to Do in Chicago
1. Millennium Park
You certainly can’t miss this from the front of the City. It’s more than just a park. It’s an art and music venue and a brilliant piece of landscape architecture. You can attend the free concerts offered at the Pritzker Pavilion or enjoy the lawn. It’s one of the entertaining radical free things to do in Chicago. It can and should be the first stop of any Chicago visit.
- Special Feature: Jay Pritzker Pavilion hosts free concerts and events.
- Where to Stay: 12 S Michigan Ave, Chicago, IL 60603
- Hours: Open daily from 6 AM to 11 PM.
- Hidden Gem: The quiet and often-missed Lurie Garden.
2. Cloud Gate (“The Bean”)
The Bean’ is one of the most popular attractions in Chicago and no trip is complete without a selfie at the sculpture. A Chicago trip wouldn’t be complete without one of the selfies at ‘The Bean’ as this sculpture is one of the most visited in the city. Its mirror-like surface captures the city’s impressive skyline in a really cool, distorted way. Walking underneath it gives an even wilder view. It’s located right in Millennium Park.
- Special Feature: The “omphalos,” a concave chamber on the underside.
- Where to Stay: 20 S Wabash Ave, Chicago, IL 60603
- Hours: Open daily from 6 AM to 11 PM.
- Hidden Gem: Visit at sunrise for the best photos without crowds.
3. Navy Pier
A Chicago trip is not complete without visiting the Navy Pier that stretches into Lake Michigan. It is a great place for the entire family as the view is excellent from the towering Centennial Wheel and there is also a Children’s Museum. You could easily spend a couple of hours just soaking in the amazing atmosphere or in the company of friends going on a sightseeing cruise. It is a great place to hang out close to the Magnificent Mile..
- Special Feature: The 200-foot-tall Centennial Wheel with panoramic views.
- Where to Stay: 900 E Grand Ave, Chicago, IL 60611
- Hours: Open Sun–Thu 11 AM–8 PM, Fri–Sat 11 AM–9 PM.
- Hidden Gem: The Navy Pier Beer Garden for live music in the summer.
4. Skydeck Chicago at Willis Tower
For the best views, you have to visit Skydeck Chicago. On a clear day, you can see the skyline of four different states at once, so Skydeck Chicago is the place to go for the best sights. I would dare to say that one of the most memorable Chicago sights is The Ledge, the main feature of the event — a glass box that extends out from the building and makes you feel as if you are floating 1,353 feet above the city. The 103rd floor of the Willis Tower is Chicago’s skydeck, from which you can see in every direction. A true Chicago sightseeing highlight I would recommend.
- Special Feature: The Ledge, a glass balcony extending 4.3 feet out.
- Where to Stay: 20 W Adams St, Chicago, IL 60603
- Hours: Open daily 9 AM to 10 PM (hours vary by season).
- Hidden Gem: The “Pie in the Sky” pizza dinner on the 99th floor.
5. Art Institute of Chicago
The Art Institute of Chicago is one of the most popular places among travelers, where one can spend an entire day. The most visited among them is Grant Wood’s “American Gothic” and Edward Hopper’s “Nighthawks,” as the place is known for its stunning contemporary and modern masterworks. The institute also holds one of the greatest Impressionist collections outside of Paris. This is a must for any art lover visiting the area.
- Special Feature: One of the largest Impressionist art collections globally.
- Where to Stay: 17 E Monroe St, Chicago, IL 60603
- Hours: Open Mon & Thu–Sun 11 AM–5 PM (Thu until 8 PM).
- Hidden Gem: The Thorne Miniature Rooms on the lower level.
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6. Field Museum
Get ready to travel through 4.6 billion years of history here. The Field Museum contains the largest fully assembled T. rex skeleton ever discovered, SUE. It also contains Máximo the Titanosaur.. You can also see an ancient Egyptian tomb or marvel at rare gems. It’s a fantastic place for both kids and adults, and it easily counts as one of the best places to visit in Chicago.
- Special Feature: SUE, the world’s most complete T. rex skeleton.
- Where to Stay: 720 S Michigan Ave, Chicago, IL 60605
- Hours: Open daily from 9 AM to 5 PM.
- Hidden Gem: Look for actual fossils embedded in the main hall floor.
7. Shedd Aquarium
Very different in its architecture is the Shedd Aquarium, which is situated along the lakefront. Shedd Aquarium is home to thousands of aquatic species like the beluga whale, different species of penguins, and sharks. The Abbott Oceanarium offers a fantastic look at Pacific Northwest marine life. A visit here is one of the most popular things to do in Chicago, so book tickets early.
- Special Feature: The Abbott Oceanarium with beluga whales and dolphins.
- Where to Stay: 1218 S Michigan Ave, Chicago, IL 60605
- Hours: Open daily 9 AM–5 PM (weekends until 6 PM).
- Hidden Gem: The seasonal Stingray Touch experience (May–Oct).
8. Chicago Riverwalk
One of the highlights of the Riverwalk is this beautiful and leisurely promenade and collection of lovely parks along its Old Town south, and a lovely train bridge. There is a very mouthwatering selection of bars, restaurants, and tasty food shops serving ice cream and other treats. And of course, there is nothing better than a lazy afternoon sitting on the banks of the river watching the river traffic. A perfect Chicago sightseeing activity for an afternoon.
- Special Feature: Architectural boat tours depart from here.
- Where to Stay: 85 E Wacker Dr, Chicago, IL 60601
- Hours: Open daily from 6 AM to 11 PM.
- Hidden Gem: The stepped seating at The River Theater for a quiet break.
9. Michigan Avenue
Michigan Avenue attracts the most attention from visitors to the city and is best known for the section called the Magnificent Mile. The stores include the Wrigley Building and dozens of high-end shops and major department stores. For an afternoon full of city bustle, relax and wander around the avenue.
- Special Feature: The Magnificent Mile, a world-famous shopping district.
- Where to Stay: 108 E Superior St, Chicago, IL 60611
- Hours: Varies by store; generally 10 AM to 8 PM.
- Hidden Gem: The Original Billy Goat Tavern on Lower Michigan Ave.
10. Wrigley Field
Even if you’re not a baseball fan, a visit to historic Wrigley Field is a must. And bonus, it is the Home of the Chicago Cubs, it’s one of the oldest ballparks in the country. The outfield walls and hand-turned scoreboard were also charming. They made the game feel timeless. The game along with the ballpark tours is the players’ unforgettable experience and also a hallmark.
- Special Feature: Iconic ivy-covered brick outfield walls.
- Where to Stay: 3630 N Clark St, Chicago, IL 60613
- Hours: Varies based on game and tour schedules.
- Hidden Gem: The historic, hand-operated center field scoreboard.
11. The Second City
Want a good laugh? The Second City is known because of famed comedians who started there. Some of them are Bill Murray and Tina Fey. Their improv and sketch comedy is always original and witty. Seeing a show here is a great way to see future comedy icons and a perfect idea for what to do in Chicago for a weekend.
- Special Feature: The birthplace of modern improv comedy.
- Where to Stay: 1816 N Clark St, Chicago, IL 60614
- Hours: Shows typically run evenings; check the schedule online.
- Hidden Gem: Catch a show at the smaller, more intimate e.t.c. Theater.
Travel Basics & Tips
- Get a Ventra card for easy bus and ‘L’ train travel.
- Save money on the top things to do in Chicago with a CityPASS.
- The weather changes quickly; pack layers to stay comfortable.
- Many free things to do in Chicago include Millennium Park and Lincoln Park Zoo.
- Old-fashioned places such as the Green Mill are cash only.
- When doing all of the Chicago sightseeing, make sure that you are wearing comfy shoes as there is a lot of walking involved.
Conclusion
And Chicago is certainly not short of fabulous attractions. It offers The Bean, where you can see your reflection, and a historic jazz club that offers other wonderful attractions. My list is never truly finished, which is the perfect excuse to plan my next trip back. I hope this guide to the best things to do in Chicago helps you create your own great trip and you fall in love with the Windy City just like I have.
