All Articles The perfect 3 days in Chicago

The perfect 3 days in Chicago

The Chicago skyline behind a sandy beach on the shores of Lake Michigan
Maria Kirsten Adelmann
By Maria Kirsten Adelmann26 Mar 2023 9 minutes read

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.


A boat navigates the Center River for the Chicago Architecture Cruise

MORNING: Hit the Loop

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.

AFTERNOON: From deep-dish to skyscraper

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.

Travelers say: “I live in a Chicago suburb, and the Chicago Architecture Center River Cruise is my favorite thing to do in Chicago. Every time I take it, I am blown away by how beautiful Chicago is and am amazed by how much the docents have to teach me about Chicago architecture.”—@Mark T


EVENING: A swanky supper club and sketch comedy

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.

Worthy detours along the way


The Cloud Gate sculpture, also known as "The Bean," with visitors walking around it and the skyline in the background

MORNING: A walk in the park

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.

AFTERNOON: Art highlights, from Nighthawks to American Gothic

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.

Travelers say: “This museum went above and beyond my expectations. It is an incredibly large and diverse museum covering so many aspects of art from every corner of the world. I have been to all the impressive museums like the Met, Louvre, and Uffizi and I was still impressed with the enormous collection here.” —@GlobeRunner22


  • The museum offers excellent free tours daily, including a 30-minute “Start Here Tour” (think of it like an orientation) and a 45-minute “Gallery Tour” that focuses on museum must-sees and hidden gems.
  • If you’d rather go it alone, you can explore the highlights with interactive online guides or The Art Institute of Chicago app, where you can read about different works as you wander. The app also has a great audio tour of various collections—just don’t forget to pack your headphones!
  • The Skip-the-Line Art Institute of Chicago Semi-Private Guided Tour is a major win for art lovers with knowledgeable guides that add context and history to the museum’s collection. Groups are limited to eight and tickets are included in the price.

EVENING: Dinner and an outdoor show

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.

Worthy detours along the way


A sunny, blue-sky day at Wrigley Field, with crowds filling the seats surrounding the green baseball field

MORNING: A pretty Magnificent Mile

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.

Travelers say: “A meticulously renovated museum that showcases the architecture and decor of a wealthy Golden Age ‘merchant prince’… There are opulent Tiffany lamps stained glass windows, centerpieces, vases.…The walls, fireplaces, and parquet flooring is different in every room. Really a gem.” —@janm511

AFTERNOON: Ride the Ferris wheel at Navy Pier

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.

EVENING: Take me out to the ballgame

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.


  • Chicago-style food is definitely a thing. Take a deep dive on the Chicago Favorites Ultimate Food & Walking Tour and taste the city’s most iconic bites, from pizza to Italian beef sandwiches.
  • Go donut shop-hopping on the Underground Donut Tour and get a taste of this city's awesome donut scene.
  • If you’re here for the deep-dish (who could blame you?), Chicago Pizza Tour takes you to some of the best pizza places in the city to try four different types of pie.

Worthy detours along the way

Know Before You Go

Late spring through early fall are ideal times to visit Chicago, with temps in the 70s and 80s. Plus, there’s a lot going on: baseball games at Wrigley Field, music festivals like Lollapalooza and Pitchfork, and free movies in Millennium Park. If the nickname Windy City wasn’t a hint, winters in Chi-town can be downright frigid. Holiday lights and hotel deals may not warm you up, but they do help.

Chicago is a major American city with things happening every day of the week, but if you have to choose days to visit, go with Thursday-Saturday. Somewhat out of step with other big cities, Csome Chicago attractions are closed Tuesdays and Wednesdays, instead of or in addition to Mondays. The Driehaus Museum (closed Monday and Tuesday), The Art Institute of Chicago (closed Tuesday and Wednesday), and The American Writers Museum (closed Tuesday and Wednesday) are among them. Restaurants are sometimes closed on Sunday and/or Monday, and occasionally even Tuesday.

In general, cafes open at 7 a.m. and deep-dish (and everything else Chicagoans eat) is on offer from around 11 a.m. to 11 p.m., depending on the restaurant. Chicago has a strong diner scene, with most closing shop in the mid or late afternoon. Bars are open until 2 a.m. but some keep the party going until 4 a.m. Shops tend to be open between 10 a.m. and 6 p.m.

The Loop: Smack-dab in the heart of the action, hotels in the Loop are convenient to major attractions, theaters, shops, and restaurants. Plus, the area is jam-packed with architectural wonders. The Pendry Chicago is an impressive 1929 Art Deco skyscraper with a shiny black facade. Inside, the hotel is modern with a dash of Gatsby-era glam. (Picture gilded, velvet, and marble details.) You’ll also find a cozy lounge-like bar and a second rooftop bar for cocktails with a side of city views. Word of warning if you’re coming by car: Hotel parking fees in this area are steep.

Magnificent Mile: The Magnificent Mile is super central (and a sightseeing hub), with easy access to the Navy Pier and the Loop. The area is packed with upscale chain hotels—like Sofitel Chicago Magnificent Mile—that have everything you need: spacious, modern rooms, a restaurant, a bar, and more. If you’re traveling by car, expect parking to be a major added expense.

West Loop and beyond: Hostels, affordable mid-range hotels, and homey B&Bs are scattered beyond the two main tourist hubs mentioned above. Distance varies, so make sure to check where the nearest transit stop is and how long it takes to get into the city. If you want to feel like you’re staying at a friend’s really fancy apartment, check out The Publishing House Bed and Breakfast in the West Loop. Via public transit, it’s about 20 minutes to Millennium Park and 30 minutes to Navy Pier. It’s a win-win with free parking and free breakfast.

Public transportation: Chicago public transit is generally safe, affordable, and convenient. Buses and metro/trains (also called the L) are run by CTA in the city and Pace and Metra in the suburbs. After two rides, Day or Multi-Day Passes are worth it. You can buy single tickets, but a reloadable Ventra Card is more convenient—or just download the Ventra app on your phone.

By bike: With a flat landscape and hundreds of miles of bike lanes and paths, Chicago’s a surprisingly bikeable city. Bikes are affordable to borrow through the city’s bike share system, Divvy Bikes. If you’re not comfortable with urban cycling, Lakefront Trail is a very rideable 18-mile trail that runs along the water.

By taxi: Taxis are notoriously pricey in Chicago but easy to find downtown or via Chicago’s taxi app, Curb. Lyft and Uber are also available but aren’t necessarily cheaper.

By car: Parking can be difficult and pricey, particularly in the city center. It’s not uncommon for hotel parking to cost an extra $75 a day in the downtown area. It even costs a fee to park at the zoo—an otherwise free attraction.

Airport transfers: Your best bet from O’Hare International Airport (ORD) is to take the Blue Line on the L (train). It departs regularly, costs about five bucks, and you’ll get downtown in around 45 minutes. A taxi can easily take longer in traffic and cost around $50. Shared cars or shuttles will be around $35.

The fastest and cheapest option from Midway Airport (MDW) is also the L, this time on the Orange Line with a trip downtown taking about 30 minutes. Taxis can cost about $40, with trips sometimes taking an hour in traffic.

Maria Kirsten Adelmann
Maria Kirsten Adelmann has lived in the US and Europe and once traveled around the world on a ship, visiting ports in Asia, Africa, and beyond. She has written hundreds of reviews of hotels, cruise ships, and travel products.