2 perfect days in Chicago

Chicago’s packed with all the things you love about a big city: towering skyscrapers, inventive restaurants, art museums, green spaces, and so much more. And while you won’t be able to do it all in two days, with a little planning you can cover a lot of ground.

With the help of Tripadvisor reviews and ratings, we’ve filled this itinerary with the very best the Windy City has to offer. We’ve organized days by location, so you’re not trekking back and forth across town, and built in breaks for you to refuel with tasty local treats that go beyond deep-dish (although we’ve got a few recs for that, too).

Start your day with a caffeine-and-sugar kick at Do-Rite Donuts & Chicken, a cherished Chi-town chain serving up some of the city’s best donuts. (The Buttermilk Old Fashioned never disappoints.) It’s located on the ground level of the Willis Tower—one of America’s tallest buildings—so after you’ve had your fill, ride up to the top and take in the seriously impressive 360-degree views of Chicago and beyond—on a clear day, you can see four states. Feeling adventurous? Stand on the glass balcony. (Note that it’s always a good idea to book a timed ticket for the Willis Tower in advance, especially in summer.)

Next up, walk through downtown Chicago—also known as the Loop. Marvel at skyscrapers as you take a 15-minute stroll to Daley Plaza, home to a city market (Thursdays), Christmas Market (November and December), and public art piece by Picasso (always). Don’t miss the sculpture by Miro, nestled between two buildings in Brunswick Plaza next door.

From here, it’s just a five-minute walk to the Chicago Cultural Center. It’s free to pop inside this former public library and admire the architecture, including two giant Tiffany glass domes. Nearby, Garrett Popcorn Shops sells Chicago-style popcorn, a sweet and savory combo of cheese and caramel that makes for a tasty souvenir.

We’re pretty sure you aren’t allowed to leave Chicago without eating a deep-dish pizza. Legendary Chicago chain Giordano’s serves up a classic version—just be warned that you’ll be waiting at least 30 minutes for your pie.

Walk it off with a stroll through Millennium Park, the city’s massive green space. Take a few selfies at the mirrored bean-shaped sculpture Cloud Gate, nicknamed “The Bean,” then stop by Crown Fountain, where a huge video screen displays faces of Chicagoans spitting water into a reflecting pool all summer. Hot day? Take your shoes off and splash around.

It’s a quick hop over to your next stop, The Art Institute of Chicago. Visiting this museum is as essential as eating deep-dish. You can easily spend hours exploring the vast collection of Impressionist art, a quirky paperweight exhibit, dollhouse-like miniature rooms, and plenty more. Don’t miss American classics like Edward Hopper’s Nighthawks and Grant Wood’s American Gothic, not to mention the stunning stained-glass windows by Chagall and impressive gift shop. The museum is closed Tuesday and Wednesday, so plan accordingly.

FOOD TOUR OPTIONS, CHICAGO-STYLE

The Loop is overloaded with exceptional restaurants, including Michelin-starred must-tries and Tripadvisor faves. Top of the list? The charming Italian restaurant Acanto, which serves up craft cocktails, award-winning wines, and a mean lobster pasta.

Round out your day with some nighttime entertainment. In the summer, Millennium Park holds free outdoor concerts and movies at Pritzker Pavilion (typically Mondays, Tuesdays, and Thursdays starting at 6:30 p.m.). Or, take the bus up to Second City. This is one of the country’s most famous sketch comedy clubs, known for launching comedians like Bill Murray, Tina Fey, and probably half the cast of SNL. Get tickets ahead, and you might see the next big name.

Grab a hearty American breakfast at the Pittsfield Café, a no-nonsense diner tucked almost secretly inside the Pittsfield building. Then, make your way to the Chicago Riverwalk and hop aboard the Chicago Architecture Center River cruise. This impressive tour is a must-do, covering over 50 remarkable buildings. Chicago is the birthplace of the skyscraper, after all.

From the Riverwalk, cross the DuSable Bridge and stroll north on Michigan Avenue, also known as The Magnificent Mile. This busy main drag is packed with shops (open around 10 a.m.) and skyscrapers like the famous Wrigley Building and Tribune Tower.

Hungry? Stop for lunch at the multi-award-winning Purple Pig and chow down on pork belly and crispy pig ears.

Next up is the Richard H. Driehaus Museum (open Wednesday—Sunday), an impressive, restored Gilded Age mansion that takes you back to Chicago’s heyday. It’ll take at least an hour to admire the carved woodwork, stained glass windows, and Tiffany lamps.

Then, hop on public transit (or walk, it’s a mile) to the massive Navy Pier, packed with carnival rides, restaurants, a Shakespearian Theater, and plenty of places to hang out and relax. It’s also home to the giant Centennial Wheel, built to honor the original Ferris Wheel that debuted at the 1893 Chicago World’s Fair. The views from up top are next-level.

The pier is a great place to grab some classic Chi-town treats for dinner. Try a Chicago-style hotdog from Billy Goat Tavern (responsible for the Cub’s epic losing streak, according to legend). Then, hit up The Original Rainbow Cone for a towering ice cream cone stacked with five flavors.

You could extend your visit to the pier through the evening; with free movies, concerts, and fireworks all summer, plus shows at Chicago Shakespeare Theater, there’s plenty to do. But since it’s your last night in Chi-town, check out a nighttime baseball game at Wrigley Field. It’s worth it just to see the iconic 1914 Cub’s stadium—and you might even catch a celeb guest performing “Take Me Out to the Ballgame” during the seventh-inning stretch.