17 Best Things to do in Chicago
Updated: Jan 23
The Top Paid and FREE Activities to Enjoy in the Windy City
Chicago, you have to go experience it for yourself. Each neighborhood has its own unique vibe. There is so much to see and do here, you are bound to love it.
From Andersonville to the Loop to Little Italy. Chicago is huge and it all deserves to be explored. Find locally owned bakeries, shop until you drop downtown, and walk more than you probably ever plan to.
If you haven't yet visited Chicago, this is your sign to go! You can eat all the delicious food you possibly can, learn about Midwestern history, admire architectural styles throughout the city, sip on coffee and devour fresh donuts.
Read Also: The Best Cafes in Chicago
If you want to visit multiple museums and attractions, save money and check out the Chicago City Pass! With a pretty limitless list of things to do, we've narrowed it down so you can see the best of the city in a short amount of time! Check out the best things to do in Chicago.
What to do in Chicago
1. Cloud Gate
You can't visit Chicago without seeing Cloud Gate, or The Bean, for yourself. This beloved, well-known sculpture sits in Millenium Park and is free to visit. Get your camera out and be ready to take fun selfies on the reflective surface of The Bean.
2. Navy Pier
While there are stores and restaurants, a children's museum, a Ferris wheel, and more to enjoy at Navy Pier, it is a fun, lively place to walk around and admire for free. If you'd like, stop for an ice cream or a hot slice of pizza at this true Chicago classic!
3. Sky Deck
Get the best view of Chicago from the top of Willis Tower in the Sky Deck! Tickets are required to be purchased in advance, but this view is totally worth it. This is also included the Chicago City Pass!
4. Magnificent Mile
This is a great street to walk down and really get a feel for the bustling vibe of Chicago. With stores up stores on the Magnificent Mile, this is the perfect spot to go shopping all day. It's also really pretty during the holidays with tons of lights and decorations.
5. Lincoln Park Zoo
A free zoo?! Yes please, let's go! The Lincoln Park Zoo has FREE admission which is perfect if you want to squeeze in a quick stroll around to admire the animals. And next door is the Lincoln Park Conservatory which is a free botanical garden!
6. Garfield Park Conservatory
If you enjoy the beauty of nature, you definitely need to head to the Garfield Park Conservatory! This is another free conservatory, although it is bigger and homes more plants than the Lincoln Park Conservatory.
7. Water Tower Place
Along with lots of shopping and dining options, Water Tower Place is a classic Chicago building. Even if you don't want to spend money in the stores, it's a pretty area to walk around. Check out the City Gallery in the Historic Water Tower right next door!
There are so many incredible museums to visit in Chicago. From history to science to art and more, the options are endless. There really is a museum for everyone to enjoy in Chicago. Check out the best museums in Chicago here!
9. Buckingham Fountain
A beautiful, and free, sight to see in Chicago is Buckingham Fountain. Located in Grant Park, this is one of the biggest fountains in the world. The details are gorgeous and it is a Chicago must-see classic.
10. Architecture River Tour
Cruise down the Chicago River, sip on cocktails, and learn all about the interesting architectural styles found throughout the city. The Architecture River Tour is a very fun way to see lots of the downtown area and learn about some Chicago history as well!
11. Montrose Beach
You can't visit Chicago without a stroll on one of its "beaches." Because it is located right on Lake Michigan, Chicago boasts some pretty lakeshore beaches, one of the best being Montrose Beach. It is free to walk down and has some beautiful views! Another great option is Fullerton Beach.
12. Alfred Caldwell Lily Pond
You might be surprised by how much nature you can find in the bustling city of Chicago. With tons of parks, huge potted planters, and tree-lined streets, you can still get in your nature fix here. One of the BEST parks to visit is the Alfred Caldwell Lily Pond. This beautiful oasis is a must-visit in spring and summer but sadly closes in fall and winter.
13. Lincoln Park
Not only is Lincoln Park a gorgeous neighborhood in Chicago, but it is also a massive 1,200-acre park that follows the lakeshore of northern Chicago. If the weather is nice, you can spend a day exploring this park and stop by nearby attractions such as Lincoln Park Zoo and Peggy Notebaert Nature Museum.
14. Rooftop Bars
If you enjoy having a drink with a view, head to one of Chicago's many rooftop bars. One of the best in town is Cindy's Rooftop, located at the top of the Chicago Athletic Association Hotel. While quite expensive, it makes for a fun, memorable night in the city.
15. Harold Washington Library
Another free activity in Chicago is the Harold Washington Library. And I'm not telling you to go check out some books, although it houses more than 1 million books, but check out these cool things to do in Harold Washington Library. It is a seriously beautiful building.
16. Baseball Game
If you're a sports fan, head to Wrigleyville, where Wriglefield, the home of the Chicago Cubs, is located. You might be in town for a big game, but even if you're not, it's still a fun Chicago activity to check out. Or if you're not a fan, check out the White Sox.
17. Musical, Show, or Concert
Did you know you can catch a plethora of shows, musicals, and concerts in Chicago? With a variety of Chicago Broadway shows to choose from, see top performing musicals, or look in advance to see if your favorite artist will be performing!
If you haven't been to Chicago yet, this is your sign to book a trip now! With an incredible variety of things to do, the list could go on forever. But these are some of the best things to do in Chicago.
When you visit a new city, what is something you always try to do? Find a museum? Look for a botanical garden? Well lucky for you, Chicago has it all! This is a must-visit travel destination in the US.
Now you know what to do in Chicago, where will you be heading first? Let's chat about this wonderful US city in the comments below!