No matter what kind of vacation vibe you want to roll with, the Windy City has you covered. Chicago is the Midwest’s big-hitter, blending top-notch museums and iconic landmarks with hip neighborhoods and views across the silvery waters of Lake Michigan.
Whether you’re here for a break packed with iconic Chicago landmarks such as the Bean, the Chicago Picasso or Navy Pier, a cultured circuit around museums and theatres, or some chill-out time in up-and-coming burbs like the North Side’s Andersonville, Chicago keeps the good times rolling.
To make things easy, most parts of the city can be reached by L or Metra train, but with so much on offer, where do you start? Listen to the locals, of course. Here are the 10 best ways to experience Chicago like those who know it best – before you know it, you’ll be navigating the Windy City like a pro.
1. Take yourself out to the ball game
As the home turf of the Chicago Cubs (at historic Wrigley Field), the Chicago White Sox (MLB), the Chicago Bears (NFL), the Chicago Bulls (NBA), the Chicago Sky (WNBA), the Chicago Blackhawks (NHL), the Chicago Fire FC (soccer) and the Chicago Red Stars (NWSL), it’s safe to say that Chicago is a sports town.
On any given day, you’ll find a game somewhere, with fans filling up arenas, stadiums and bars, and rooting for their favorite players. Plus, Chicago has a long legacy of league championships, so there’s a good chance of catching a make-or-break game featuring top talent.
Planning tip: Tickets to major games sell out quickly, so book seats well in advance if there’s a particular match you hope to catch. Accommodation prices also shoot up at peak times, including during championships – book ahead to avoid disappointment.
The perfect 48 hours in Chicago
2. Dive into Chicago’s cocktail scene
The Violet Hour is said to be the birthplace of craft cocktails in Chicago, and no visit would be complete without a drink at one of the city’s original speakeasies. Look for a yellow light on North Damen Avenue in Wicker Park marking the bar’s entrance – if the light is on, they’re open for business.
Once you cross the threshold, the lights dim, and sound hushes behind towering velvet curtains that open to reveal a sleek space for sipping the creations of the house mixologists. Be sure to keep your phone on silent and dress as if you’re meeting the parents to ensure admittance.
If you can’t get enough of Chicago’s speakeasies, add The Drifter to your list. It’s 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).
Another top pick is Lady Bird, nestled in the basement of the Hoxton in the West Loop. This atmospheric bar features live music (jazz, soul and rock) Thursday through Saturday and it evokes a nostalgic 1960s glam.
3. Find Chicago’s magic
Some of the most prominent magicians in the industry reside in Chicago, so it’s little wonder the city has become the hub for a burgeoning magic scene. In the Loop, spectators can get dolled up for an intimate night of misdirection with Dennis Watkins, a third-generation magician, at the opulent Palmer House Hilton. Dress well to fit in with this smart crowd.
If you prefer something more laid-back, head north to the Chicago Magic Lounge on North Clark Street. In true magic show fashion, the entrance is disguised – as a laundromat. A wall of washing machines swings open to reveal a host ready to guide you to the auditorium show or the bar, where bartenders serve up close-hand magic alongside delicious drinks.
Planning tip: The Magic Lounge hosts a family matinee show every other Sunday, open to everyone aged five and up – perfect for the whole family!
4. Groove to the Chicago blues
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.
5. 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.
6. Dine at award-winning restaurants
Over the years, Chicago’s reputation as a culinary destination has flourished. You’ll find well-loved stalwarts like deep-dish pizza parlor Gino’s East, but also imaginative new openings popping up all over the city.
The James Beard Awards arrived in Chicago in 2015, with plans to stick around until 2027, largely thanks to local chefs such as Grant Achatz, Stephanie Izard, Bill Kim and Carlos Gaytan. For high-end dining, head to the West Loop and take your pick of top culinary artists. Joe Flamm’s Rosemary, an Italian-Croatian restaurant, is one of the city’s hotspots, while Swift & Sons caters to the power dining crowd, and the scattered branches of Beatrix deliver top-notch brunch.
For anyone looking to splurge, book a reservation at Next for their unique dining experiences. For more low-key, budget-friendly fare, head to the Athenian Room in Lincoln Park and try their chicken kalamata (a Tina Fey favorite). Other reliable spots include Oasis in the Loop (located in the back of a jewelry shop) and Carniceria Aguascalientes on West 26th Street in Little Village.
7. 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 by Frank Gehry’s swooping silver Jay Pritzker Pavilion as the sun dips and gorgeous live music fills the twilight air.
Planning tip: Check out the schedule of free summer concerts in Millenium Park – jazz and world music on Mondays and Thursdays, and classical music on Wednesdays, Fridays and Saturdays as part of the Grant Park Music Festival.
8. 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. The river cruise run by the Chicago Architecture Foundation is popular with architecture buffs; it now runs during the day and at sunset with indoor and outdoor seating.
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.
9. Feel the fun of the fair on 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 cool breezes and sweet views, especially from the vertigo-inducing, 196ft-tall Ferris wheel.
High-tech rides, splash fountains, big boats and greasy snacks blow the minds of young ones, while live music, Shakespearean theater and whopping fireworks displays entertain older visitors. A smart renovation has added inviting public plazas, performance spaces, art installations and free cultural events.
Planning Tip; The lakefront speedboat tours that leave from Navy Pier are an enjoyable way to admire the city from the water.
10. Laugh out loud at a Chicago show
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 magic with suggestions hollered up by the audience.
There’s more to see on stage than comedy. Among the city’s 200 theaters are powerhouse drama stages such as Hollywood-star-laden Steppenwolf and heaps of fringey, provocative “off-Loop” companies, such as The Neo-Futurists.
This article was first published Jun 16, 2021 and updated Aug 11, 2024.
