It’s been 8 months since I moved to Chicago, so now I can share the best things to do in Chicago as a true local. I have spent every weekend exploring new neighborhoods and famous places in Chicago and I still have a lot on my Chicago bucket list! As I continue to enjoy the Windy City, I promise to add more updates about my experiences and things to do in Chicago.
1. Explore Grant Park
Grant Park is probably one of the most touristy places in Chicago, but for a good reason. Chicago’s top attractions like Millennium Park, Buckingham Fountain, the Cloud Gate, the Art Institute of Chicago, Maggie Daley Park and many more are all located here.
During the summer Grant Park hosts hundreds of festivals and events, so if you visit it any day of the summer, you will have a new and amazing experience each time. I would plan to spend half a day in Grant Park, finding the hidden gems, enjoying the street performers and people-watching! Bring a snack for a picnic in the grass, too!
2. In Grant Park: See the Buckingham Fountain Light Show
At the center of Grant Park is the famous Buckingham Fountain. At 7 meters tall and 85 metres in diameter, the Buckingham Fountain is one of the largest in the world. The fountain is an allegory for Lake Michigan, with four pairs of sea horses representing the states of Illinois, Wisconsin, Michigan and Indiana. One of the most unique experiences in the city is the Buckingham Fountain Light Show thats happens every hour from dusk until 10pm, mid-April to mid-October depending on the weather.
3. In Grant Park: Enjoy Public Art at Millenium Park
Millennium Park is located in Grant Park and it features 25 acres of landscape, architecture and public art. Stroll around and enjoy some of the most famous sculptures and fountains as well as things you’d never expect to see.
4. In Grant Park: See your Reflection in the Cloud Gate (A.K.A. the Bean)
The first place many tourists have on their list is taking a picture with the Bean. It’s not as easy as it seems as there are hundreds of people every day taking the most creative photos with it! How creative can you be? Let your imagination run wild!
5. In Grant Park: Run Under the Crown Fountain
The Crown Fountain in Chicago uses 50-foot tall video screens with real Chicago citizens that spit on people when you least expect it. (Operates from May to October)
Designed by the Catalan artist Jaume Plensa, the Crown Fountain is very interactive, and on hot summer days you’ll see children (and adults) running around in the reflecting pools and waterfalls that cascade down the sides of the towers.
6. In Grant Park: Count the Stars at the Adler Planetarium
In Grant Park, the Adler Planetarium offers a variety of projected shows of the sky above Chicago without the light pollution and presentations about the Planet Nine and nebulae.
Date night idea: For adults over 21 looking for a fun (and educational) evening, Adler After Dark offers open access to the planetarium, unlimited shows, and unique entertainment every third Thursday of the month from 6:00–10:00 pm. (Tickets are about $20 per person)
More Downtown Chicago: Learn About Chicago Culture and History
Chicago is one of the most unique places in the United States with a rich and fascinating culture and history. Just remember the Great Chicago Fire of 1871 or the The World’s Columbian Exposition! Here was built the nation’s first skyscraper and the first, and until recently, the largest Ferris wheel. Before visiting the city, read more about its history and then visit the landmarks that shaped Chicago and the United States as a whole.
7. Visit the Science and Industry Museum
The Science and Industry Museum is the old Palace of Fine Arts, built in 1933 in Jackson Park for the World’s Columbian Exposition.
Here you will find a full-size German U-505 submarine captured during the Second World War, a stainless steel diesel locomotive from 1934 and the first Boeing 727 to enter commercial service. Be sure to visit the Science Storms exhibit, which has a Tesla coil, Foucault pendulum and Wimshurst machine. This museum is the best science museum I have ever visited!
Address: 5700 S Lake Shore Dr, Chicago, IL 60637
8. Meet Sue at the Field Museum
One of the best and largest natural history museums in the world, the Field Museum has more than 24 million objects. This place will feed your fascination for the natural world. And don’t forget to meet SUE, the T-Rex and a few pharaohs!
Address: 1400 S Lake Shore Dr, Chicago, IL 60605
9. The Art Institute of Chicago
Whether or not you’re an museum buff, you have to go here! The Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist painting outside Paris! with more than 30 paintings by Monet, as well as works by van Gogh, Cezanne, and Toulouse-Lautrec. For modern art there’s Jackson Pollock, Warhol, Jasper Johns and Matisse! This is a great place to get introduced to some of the world’s most famous artists!
Address: 111 S Michigan Ave, Chicago, IL 60603
10. Listen to Jazz
To fully dive into Chicago’s jazz and blues, look for the venues that have legendary status.
Visit the Kingston Mines in Lincoln Park, which dates back to 1969 and has two live shows a night or the Green Mill Cocktail Lounge (1907), which was run by mobsters in the Prohibition era.
Overall, there are more than 200 live music venues, so you will find something anywhere you go!
Bonus Tip: Plan Your Trip Around Jazz festival
This totally free four-day music festival takes place at the end of the summer in Millennium Park. The list of performers who have taken the stage at the Chicago Jazz Festival include Dizzy Gillespie, Ella Fitzgerald, and Sun Ra.
11. See a Show at the Chicago Theatre
One of five Tony award-winning venues in Chicago, the Chicago Theatre needs a visit, even if you’re not planning to see a show.
The famous vertical sign often appears in movies and the facade of the house is magnificent!
12. Take an Architecture Cruise
Among many other river and lake cruises in Chicago, the Architecture Cruises are the best ones! Go with the Chicago Architecture Foundation River Cruise, and hear fascinating stories behind more than 50 buildings along the Chicago River. It’s a great experience!
More Things to Do Downtown Chicago
13. Go Shopping on Magnificent Mile
With 275 restaurants and more than 460 retailers, Michigan Avenue is a whole world of shopping, entertainment, dining, and more things to do than you could manage in a whole holiday.
Bonus Tip: Stop and see the Chicago Water Tower, dating to 1869, the second oldest surviving water tower in the United States.
13. Visit the First United Methodist Church of Chicago
Why would you want to visit a church on your vacation? While exploring downtown Chicago, you may be surprised what you find when you look up. Dating back to 1831, the First United Methodist Church of Chicago is the city’s oldest church and tallest church building in the world. The building has 21 floors and reaches 568 feet into the air. At the very top of the building, in the top spire, 400 feet above the noisy city streets, sits the Sky Chapel.
Bonus tip: You can take a free tour of the Sky Chapel Monday through Saturday at 2:00 p.m. or Sunday at 9:45 a.m. or 12:15 p.m.
Downtown is Cool, But You Have to See Other Chicago Neighborhoods
14. See the Animals at the Lincoln Park Zoo
Dating back to 1868, this zoo is one of the last remaining free admission animal parks in the United States. You can see more than 1,100 animals here, including polar bears, African penguins, giraffes, pygmy hippos, ostriches, gazelles and many more.
15. Stroll, Run, or Bike on the Lakefront Trail
Eighteen miles of Chicago’s shoreline can be accessed on a waterfront path, threading through all of the city’s lakeside parks. People use the trail to get to work, exercise, and to stroll next to Lake Michigan and gaze at Chicago’s skyline. There are bike rentals all along the trail, or you could get a day pass for Divvy, Chicago’s bike-sharing system.
16. See the Cubs Game
Even if you are not a baseball fan, go see a Cubs game at Wrigley Field. It is synonymous with Chicago and a visit to the city would be incomplete without it! For a true experience, have a Chicago-style hot dog during the game!
17. Find all of the Wizard of Oz Characters at the Oz Park
This whimsical and hidden away Oz-themed park had a wonderful impact on the surrounding neighborhood, providing a safe, clean space for both tourists and the resident community alike. . The park features Dorothy’s Playground and the Emerald Gardens. And, if you wander around long enough, you will see the Tin Man, Scarecrow, Cowardly Lion, Dorothy, and Toto. (A fun activity if you have kids!) Each character was created by local artist John Kearney.
Find Your Favorite View of Chicago Skyline
You can see the beautiful Chicago skyline from the beach, the lake, some of the tallest buildings in Chicago, or a rooftop patio! Try them all and tell me which one is your favorite in the comments below!
18. Views From the John Hancock Building
At the Magnificent Mile (right next to the Water Tower), the iconic John Hancock Building, offers breathtaking views of the city skyline and Lake Michigan. You can visit the 360 Chicago observation deck. Here you will find the TILT, a moving platform that tilts you over the Michigan Avenue from the 94th Floor. (Admission is about $20 per person.) Instead, I recommend going to the Signature Room. It’s located on the 96th floor and you can relax and enjoy the best views of the city for the price of a glass of wine or beer!
875 N Michigan Ave, Chicago, IL 60611
19. Feel Like You’re Floating above Chicago at the Willis Tower
The Willis Tower, the second-tallest building in the Western Hemisphere, provides an amazing view of the cityscape. For a unique experience, you can visit the famous 103rd floor Skydeck with walls, floors, and ceilings made entirely of glass, allowing visitors to enjoy a unique and view of Chicago’s architectural landscape. On a clear day you can see up to 50 miles ahead and four states!
233 S Wacker Dr, Chicago, IL 60606
20. Go to a Scenic Spot and See the Chicago Skyline
Beaches and parks, including the Oak Street Beach, the North Avenue Beach, and Lincoln Park offer some of the best views of the skyline! Those are my favorite spots for pictures and Sunday afternoon strolls!
Even More Things to Do – Summer in Chicago
Chicago is one of the best places to visit any time of the year, but especially during the summer months! With festivals, events, and beautiful weather in the city, everyone is ready to celebrate the end of winter. And by the end of August, you will notice all Chicagoans putting on Wolf hide and saying “ Winter is coming”. Yes, the best time to visit is May to August!
21. Have a Picnic in the Lincoln Park
Lincoln Park is huge and very family-friendly! With the zoo nearby, pack a lunch with you and see everything Lincoln Park has to offer!
22. Go to the Beach and Actually Swim in Lake Michigan
I couldn’t believe it, but Lake Michigan is warm enough to swim in! Also, there are a lot of really nice beaches in the city, where locals come to spend their weekends with their families and friends! If this is the only vacation you are taking this summer and want to get your water adventures in, I highly recommend going to the beach in Chicago!
23. Attend One of Many Chicago Summer Festivals
As I’ve mentioned, Chicago truly comes alive in the Summer! See Eventbrite and Facebook Events when you visit and you will find anything from a German Beer Festival to Retro on Roscoe to a Rib Festival and many more!
24. Take a Lake Booze Cruise
I found a really cheap offer for the Lake Booze Cruise on Groupon and it was something else! If you are looking to party, you will love it, as you are going to shake your booty with a view of the Chicago Skyline! But, if you would just like to have a couple of drinks and take it slow, step outside on the deck and enjoy the sunset over downtown Chicago. The views are fantastic!
25. If You Have Time, Go to the Navy Pier
Last (and least), visit the Navy Pier! I know, this is probably the most unpopular opinion, but I really don’t understand what the fuss is about. I have visited the Navy Pier twice and all I found is fast food and souvenir shops. The parks around it may be nice, but this is the most touristy spot I have seen anywhere. If you went to the Navy Pier and enjoyed it, please let me know in the comments below what were your favorite parts of the Navy Pier. I don’t think you will find many locals going to the Navy Pier on the weekends!
What things to do in Chicago interest you the most? Let me know in the comments below! Are you a jazz fan, a foodie, or a beach bum? You will find it all in Chicago!
September 1, 2019
Marina, I have lots of relatives to visit in a small town outside of Chicago, but I rarely take the time to go into the city. I think your post has inspired me to schedule more play time into my next visit, and head into the Windy City!
September 1, 2019
I keep finding new places in Chicago and I love it so far! Hope you will make more visits soon!
September 5, 2019
There’s really a LOT to do in Chicago! Hopefully, I’ll make it to the states one day again because I definitely want to visit Chicago! Nice post!
September 5, 2019
I have never been to Chicago. All the places mentioned above looks very attractive. Cloud gate and Architecture Cruise looks amazing. Adding to my travel list. Thanks for sharing.
September 5, 2019
Chicago is on my US bucket list! I loved your ideas! I hope to visit soon!
September 6, 2019
Thank you so much for sharing this. I’m going to Chicago next month for a concert, and have been too busy to research things to do there. So, this is helpful. I’ll be pinning this so I can refer to when I’m putting together the itinerary for my trip.
September 6, 2019
I’ve been to Chicago twice but both times weren’t more than just a few days! I’d love to go back for sure! I did go to Navy Pier…while I was reading your post, I wondered if you were going to include the ferris wheel on the pier – & sure enough you did! I went on with my friends & it was amazing!
-Madi xo