3 perfect days in Chicago

Packed with towering skyscrapers, Gilded Age mansions, vibrant public art, and loads of local pride (go Cubs!), Chicago could easily take days to explore. But if you’re short on time, or visiting for a long weekend, you can do most of the must-sees in three days—all you need is the right itinerary.

That’s where we come in. We’ve created a schedule that balances hitting the highlights with downtime that doubles as sightseeing (outdoor concerts, comedy shows, and more). To save you time, we’ve bundled each day’s activities by neighborhood, so you’re not walking around in circles—even in the Loop. Best of all, we’ve used Tripadvisor reviews to find the spots travelers love most, so every stop is a winner.

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° 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 a 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 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 along the Chicago Riverwalk. This is also where you’ll find the departure point for 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.

CHICAGO ARCHITECTURE TOUR OPTIONS

Right across the river is the chic Tortoise Supper Club (open Tuesday-Saturday, book ahead) with ‘20s vibes, inventive cocktails, and delicious Chilean sea bass. You could kick back here all night—check the schedule for live jazz shows—but we’d vote for heading north 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 of time, and you might see the next big name.

Start your morning exploring Chicago’s famous Millennium Park, the city’s massive green space. Take a few selfies at the mirrored sculpture Cloud Gate, nicknamed “The Bean,” then stop by Crown Fountain, where a massive video screen displays faces of Chicagoans spitting water into the reflecting pool all summer. Hot day? Take your shoes off and splash around.

Next, walk along the BP Pedestrian Bridge to explore the winding paths of Maggie Daley Park, then make your way south to check out the three-tiered Buckingham Fountain and the surrounding rose gardens.

Grab a hearty American brunch at the Pittsfield Café, a no-nonsense diner tucked almost secretly inside the Pittsfield building.

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 huge collection of Impressionist art, 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 the impressive gift shop. The museum is closed Tuesday and Wednesday, so plan accordingly.

ART INSTITUTE OF CHICAGO TOUR OPTIONS

The Loop is overloaded with exceptional restaurants, from Michelin-starred must-try’s to Tripadvisor faves. Top of the list? The charming Italian restaurant Acanto 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.). You can also BYOPicnic, if lobster pasta isn’t in the budget.

In the winter, you can skate the ribbon at Maggie Daley Park. (There’s a fee to rent skates and getting tickets in advance is recommended.) Whatever the season, the skyline is sure to look stunning as the sun sets and the city lights up all around the park.

Start your morning at the ornate water tower on Michigan Avenue, and walk south down The Magnificent Mile, a busy main drag packed with shops (open around 10 a.m.) and skyscrapers like the famous Wrigley Building and Tribune Tower. Take a detour to visit 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.

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

Then hop on public transit (or walk, it’s only 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 night 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.

FOOD TOUR OPTIONS, CHICAGO-STYLE