The windy city of Chicago is famed for its architecture, restaurants, and museums. Outside of the Louvre in Paris, The Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist paintings—who knew? Whatever your interests are—art or not—there are a lot of activities to choose from. But just how do you see and do it all?
Well, that’ll take some time, so we’ve created a bucket list of 10 things that everyone living in or visiting Chicago could—and should—check off their list right now. Think stepping out onto a glass sky deck on the 103rd floor, biking 18 miles along Chicago’s lakefront, and eating your weight in deep-dish pizza (it’s called balance people). Looking for more things to do here? Check out our favorite rooftop bars where frozen prosecco popsicles await you (really).
Have a Drink at The Signature Lounge on the 95th Floor
Want to see one of the best views of Chicago? Have light fare and drinks at The Signature Lounge, situated at the top of the Hancock building. Sip specialty cocktails or choose from 200 wines, along with dishes including a raw bar for two with half a Maine lobster, Margherita pizza, and chips and guacamole. Also, what better place to catch the Navy Pier fireworks than here every Wednesday and Saturday night? PS: If you’re in the mood to bounce around, check out our picks of the city’s best rooftop bars here.
875 N Michigan Avenue, Chicago
Tour Frank Lloyd Wright’s Home and Studio
Go inside the home and studio of famed architect Frank Lloyd Wright in this hour-long guided tour. Additional options include a self-guided audio tour of the neighborhood of Oak Park where there are the most Wright buildings (40 minutes), or an in-depth three-hour guided walking tour of 10 Wright homes.
951 Chicago Avenue, Oak Park
Visit the Art Institute Chicago
No trip to Chicago is complete without a visit to the Art Institute, said everyone we asked for a recommendation. Currently on view through October is the ongoing collection The New Contemporary, which includes masterworks by Andy Warhol and Roy Lichtenstein and an exhibition of photographs by Hugh Edwards.
111 S. Michigan Avenue, Chicago
Take an Architecture Tour by Boat
Like Julia Roberts’s character did in My Best Friend's Wedding, take an architecture tour along the Chicago River. Wendella's Chicago's Original Architecture Tour is a 75-minute tour offering insight on Chicago’s buildings over the span of 130 years. Chicago’s First Lady is another 90-minute option.
Wendella’s main dock is located at 400 North Michigan Ave., Chicago; Chicago’s First Lady kiosk is at 112 E. Wacker Drive, Chicago
Cruise Around Chicago’s Lakefront on Divvy Bikes
Take in the city’s sights as you bike around Chicago's lakefront. (Download the 18-mile car-free bike path here). Make a stop at Olive Park where Dan Kiley designed the landscape and views of the skyline are Instagram-worthy. While here, take a lunch break in the Streeterville neighborhood that houses some of our favorite restaurants like GreenRiver, Giordano's for deep dish (ahead on our list), and The Signature Lounge (also on our list).
Lakefront Trail, Chicago
Step Out Onto the Skydeck
If you don’t have a fear of heights, then step out onto the 103rd-floor glass Ledge at the Willis Tower (formerly the Sears Tower). The building is the second tallest in North America and offers the highest public viewing area in the States. On a clear day, you can see as far as Illinois, Indiana, Wisconsin, and Michigan.
233 S Wacker Drive, Chicago, theskydeck.com
Eat Deep Dish Pizza at Lou Malnati's or Giordano's
Every Chicagoan has a favorite pizza place. With the help of our friends, we were able to narrow it down to the two best spots: Lou Malnati's Pizzeria and Giordano's, both with multiple locations throughout the city. Peep through their Instagram accounts here and here and you’ll see why.
Have Brunch at Cochon Volant Brasserie
Hungry for brunch? You will be after seeing Cochon Volant's Instagram feed! The French brasserie serves a weekend brunch menu Saturday and Sunday from 8 a.m. to 3 p.m. Taste dishes like bacon Benedict, avocado toast ‘n’ eggs, and blueberry quinoa pancakes. Also check out weekend brunch at Michelin-starred restaurant Band of Bohemia in Ravenswood. The menu includes beignets and hot chocolate, fried chicken and French toast, and duck confit hash.
Cochon Volant Brasserie, 100 W. Monroe St., Chicago; Band of Bohemia, 4710 N. Ravenswood Avenue, Chicago
Enjoy an Outdoor Concert at Ravinia Festival
From June through September enjoy Ravinia’s outdoor summer concert series. Find the schedule here, which includes John Legend’s Darkness and Light Tour on June 10. During the summer it’s also home to the Chicago Symphony Orchestra. Guests can pack their own picnic, order a basket in advance, or dine at one of the park restaurants.
200 Ravinia Park Road, Highland Park
Head to the Museum of Contemporary Art Chicago
Opening soon (June 6 through September 24, 2017) is Takashi Murakami’s The Octopus Eats Its Own Leg, which will feature a never-before-seen artwork. (Remember this collaboration he did with Shu Uemura last year?) Other exhibitions at MCA include Chicago Works by Chris Bradley and Eternal Youth.
220 E. Chicago Avenue, Chicago
What are your favorite things to do in Chicago? Share your ideas in the comment section below.