No matter what kind of vacation vibe you want to roll with, the Windy City can cater to it.
Whether it’s jam-packed with iconic sites like the Art Institute of Chicago, the Picasso sculpture or Navy Pier or a quieter trip to chiller parts of the city like the North Side’s Andersonville, Chicago will feel like your own sweet home before long.
If you can, spend about three days in Chicago so you can do a variety of things without feeling rushed. Chicago has something for every price point, from luxury dining experiences to plenty of free things to do like exploring beautiful parks or listening to music at The Grant Park Music Festival.
But with so much on offer, where to start? Listen to the locals, of course and travel by bus or L train, like they do. Here are the 15 best ways to experience Chicago like those who know it best. Follow our Chicago traveling tips on the best things to do and, before you know it, you’ll be exploring the Windy City like a pro.
1. Take yourself out to the ball game
When you consider that the city is home to two baseball teams: the Chicago Cubs, who play at historic Wrigley Field, and the Chicago White Sox, who call Guaranteed Rate Field home, a baseball game is a must.
The rest of the year, it’s easy to see a variety of sporting events with top-tier athletes. Football fans can go to a Chicago Bears game while basketball lovers can see the Chicago Bulls and the women’s Chicago Sky basketball teams. And don’t forget Chicago Blackhawks hockey, the Chicago Fire FC men’s soccer and the Chicago Red Stars women’s soccer. It’s safe to say Chicago is a sports town.
On any given day, you’ll find a sporting event happening, with fans filling arenas, stadiums and bars to root for their favorite players. Tickets to hot games sell out quickly and hotel prices can double, especially during peak tourism seasons, so plan ahead.
2. Take an architecture river cruise
Taking a Chicago River cruise to admire the skyline and learn about this vital urban waterway is one of the top Chicago attractions. You’ll find a variety of cruises offered by Wendella, and a highly rated tour is offered by the Chicago Architecture Foundation. Even if you’re not an architecture buff, you’ll love the stories about the city’s most recognizable buildings and the people who built them. The boat tour now runs during the day and at sunset with indoor and outdoor seating.
3. Dive into Chicago’s cocktail scene
The Violet Hour is said to be the birthplace of craft cocktails in Chicago, and no visit is complete without a drink at one of the city’s original speakeasies. If the yellow light is on, it’s open. You’ll step through velvet curtains and into an upscale cocktail bar from a different era.
Be sure to keep your phone on silent and dress as if you’re meeting the parents to ensure admittance.
But the ultimate cocktail experience in Chicago may be at Aviary, which offers complex molecular drinks alone or paired with small plates with complex presentations. It’s part of the Michelin-starred Alinea Group, and so is The Office speakeasy below it.
If you can’t get enough of Chicago’s speakeasies, add The Drifter and Lady Bird to your list. The Drifter is located on the lower level of River North’s iconic Green Door Tavern, the city’s oldest drinking hole. Find the entrance en route to the bathroom behind a bookshelf. And the best part? Vaudeville shows play every hour (expect to pay a cover).
Lady Bird is nestled in the basement of the Hoxton, in the West Loop. The low-lit bar features live music (jazz, soul and rock) Thursday through Saturday and evokes feelings of 1960s glam.
4. Find Chicago’s magic
Some of the most prominent magicians in the industry reside in Chicago, and it’s no wonder the city has become a hub for a burgeoning magic scene.
In the Loop, spectators can get dolled up for an intimate night of magic with Dennis Watkins, a third-generation magician, at the opulent Palmer House Hilton – dress well, as cocktail attire is encouraged.
If you prefer something more laid-back, head north to the Chicago Magic Lounge. In true magical fashion, the entrance is disguised – as a laundromat. Step through the portal to find a host ready to guide you to a show or the bar, where the bartenders serve up close-hand magic alongside delicious drinks. If you’re visiting Chicago with kids, the Magic Lounge hosts a family matinee show every other Sunday that welcomes everyone aged five and up. Perfect wintertime Chicago outing for the whole family!
5. Groove to the blues and rock
No musical genre is as closely tied to Chicago as the blues – the electric blues, to be more precise. When Muddy Waters and friends plugged into their amps in the 1950s, guitar grooves reached new decibel levels, and the Chicago blues scene was born.
You can still hear the real deal in clubs around town, such as Buddy Guy’s Legends, where the icon himself sometimes takes the stage, or Rosa’s Lounge, where the vibe is a bit more down and dirty. Held in Millennium Park in June, the Chicago Blues Festival attracts top talent.
Planning tip: The blues paved the way for rock and roll, and you’ll find cool little venues hosting edgy indie bands slouching on many a street corner. Thalia Hall, Hideout and Reggies are good places to start.
6. Shop local in Chicago’s cool neighborhoods
Chicago is a vibrant collection of neighborhoods. To really experience the city like a local, go beyond the Loop, avoid Michigan Avenue and support local neighborhood stores that reflect the city’s diverse make-up.
Andersonville sits on the North Side and has intriguing Swedish roots. The Clark Street passage between Foster and Bryn Mawr is littered with nostalgic shops that give off Wes Anderson vibes, while Wicker Park and Bucktown tailor their scenes to local hipsters and young families.
If you continue south to Little Village, you’ll find a Mexican-dominated hub that’s the city’s second-highest-grossing district for shopping. Pop into Comercio Popular to buy from unique artisans and catch events imported straight from Mexico.
End your retail tour in Hyde Park, home to Michelle and Barack Obama (when they’re in Chicago). The Silver Room is a must – this Black-owned store features various products that put Black culture and Black artisans in the spotlight.
Planning tip: Michigan Avenue is touristy and big-brand oriented, but it’s worth visiting between Thanksgiving and Christmas for seasonal decorations and festive storefronts.
7. Dine at award-winning restaurants
Over the years, Chicago’s reputation as a culinary destination has flourished thanks to local chefs such as Grant Achatz, Rick Bayless, Stephanie Izard, Erick Williams, Bill Kim and Carlos Gaytan.
For high-end dining, head to the West Loop and take your pick of top culinary artists, Beard winners and Michelin-starred chefs.
Joe Flamm’s Rosemary, an Italian-Croatian restaurant, is one of the city’s hotspots, while Gibson’s Italia serves perfect Florentine steaks to the power dining crowd, and The Publican delivers top-notch brunch. Classics that wow include The Girl & The Goat and Frontera Grill. Head to Hyde Park for James Beard award-winning new Southern cuisine at Virtue, an Obama favorite.
For a splurge, book a reservation at Grant Achatz restaurant Next, where the concept, decor and menu change completely a few times a year.
If you’re visiting Chicago on a budget head to the Athenian Room in Lincoln Park for the chicken kalamata (a Tina Fey favorite). Lou Malnati’s Pizza makes the city’s favorite deep dish pies. Try Oasis in the Loop for Lebanese fare or Aguascalientes in Little Village for Mexican fare.
8. Make the most of Millennium Park
In the playful heart of Chicago, Millennium Park shines with whimsical public art. Go ahead, walk under Anish Kapoor’s Cloud Gate – aka “the Bean” – and touch its silvery smoothness. Let the human gargoyles of Jaume Plensa’s Crown Fountain shower you with water to cool down in summer or unfurl a blanket at Pritzker Pavilion, the Frank Gehry-designed swooping silver band shell as the sun dips, when gorgeous live music fills the twilight air.
Planning tip: Check out the schedule of free summer concerts from June to August in Millenium Park – jazz and world music on Mondays and Thursdays, and classical music on Wednesdays, Fridays and Saturdays.
9. Take a Windy City tour
Want to know all of Chicago’s secrets? Take a guided tour to uncover lesser-known facts and all sorts of insider information that will help you win Trivia Night back home.
If you want to explore Chicago’s neighborhoods more fully, book a tour run by TikTok historian Shermann “Dilla” Thomas, who leads fascinating walks through Bridgeport/Stockyard, Bronzeville or Pullman/Roseland with his company Chicago Mahogany Tours.
10. Laugh out loud at local comedy shows
A group of jokesters began performing intentionally unstructured skits in a Chicago bar a half-century ago, and voilà – improv comedy was born. Second City still nurtures the best in the biz, though several other improv theaters also work from booze-fueled suggestions that the audience hollers up.
Among the city’s 200 theaters are powerhouse drama troupes such as Hollywood-star-laden Steppenwolf, the Black Ensemble Theater and heaps of fringey, provocative “off-Loop” companies, such as The Neo-Futurists.
How to get around Chicago
11. Stroll along Navy Pier
Stretching away from the skyline and into the blue of Lake Michigan, the half-mile-long Navy Pier is one of Chicago’s most visited attractions. Its charms revolve around the cool breezes and sweet views, especially from the vertigo-inducing, 196ft(59.7m)-tall Ferris wheel. High-tech rides, splash fountains, big boats and sugary snacks blow the minds of young ones.
Live music, Shakespearean theater and whopping fireworks displays entertain everyone else. A smart renovation has added public plazas, performance spaces, art installations and free cultural programming.
12. Discover African American History at the DuSable Museum
The DuSable is the oldest independent African American museum in the United States. It tells the story of the American Black experience through notable people and events.
Current exhibits celebrate Chicago’s first Black mayor Harold Washington, showcase art collected by the publisher of Ebony and Jet magazines and offer scenes from the civil rights movement. Since it’s a nonprofit museum admission is free, though donations are appreciated.
13. Explore the sea and the stars
One of the coolest things about Chicago is that many of the top attractions are all clustered together near Lake Michigan.
Two of the most thrilling lakefront experiences will let your little ones explore the sea and the stars. Take them to the John G. Shedd Aquarium, where you’ll find massive tanks filled with angel fish and octopi, beluga whales and sharks. Stargazers will love the Adler Planetarium where they can launch a rocket or take a look into space through a giant telescope.
14. Get cultured at the Art Institute
The Art Institute of Chicago is one of the most beloved places to visit for natives and the city’s top attraction for visitors. Even if you have just a couple hours to visit, you’ll be impressed.
The museum features many famous paintings including modernist works by Mondrian and Georgia O’Keeffe, as well as dreamy impressionist paintings by Monet and Matisse. If the weather is warm, take a break in the garden cafe before going back to see the special new gallery for ancient Egyptian masks and sculpture. Be sure to snap a souvenir photo by one of the lions that guard the front entrance.
15. Enjoy the outdoors at Grant Park
Chicago has lots of cheap and free sights, making it a fun place to visit even if you don’t have a lot of money to spend.
Explore Grant Park, which has lots of gardens, benches for relaxing and views of the lake. Take the kids to Maggie Daley Park where they can let off steam climbing, playing on tube slides or crossing a suspension bridge. Bigger kids can take on the climbing wall or rent rollerblades. If you’re visiting in winter (November-February), register for tickets to the Ice Skating Ribbon.
As dusk falls, make your way over to Buckingham Fountain, a stunning 1927 landmark featuring plumes of water illuminated by colored lights every night until 11pm. Just be sure to bring your mosquito spray.
Keep planning your trip to Chicago:
Find the best times to visit Chicago.
Getting around Chicago is easier than you think – here’s how.
Explore the best free things to do in Chicago – and what to do on a budget.
Find national parks, wineries and more on these Chicago day trips.
