No matter what kind of vacation vibe you want to roll with, the Windy City can cater to it.

Whether it's a break jam-packed with iconic sites like the Bean, the Picasso structure or Navy Pier, or a quieter trip to more chilled parts of the city like the North Side’s Andersonville, Chicago keeps the good times rolling.

But with so much on offer, where to 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 exploring the Windy City like a pro.

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Exterior of Wrigley Field, Chicago
Sporting tradition runs deep at Chicago's Wrigley Field © FiledIMAGE / Shutterstock

1. Take yourself out to the ball game

When you consider the fact this city is home to 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 and the Chicago Red Stars (NWSL), it’s safe to say this is a sports town.

On any given day, you'll find a sporting event happening, with fans filling up arenas, stadiums and bars, and rooting for their favorite players. Plus, Chicago is one of the rare cities with a long legacy of championships, so don't miss out on the magic of cheering on the hometown team.

Planning tip: Tickets to major games sell out quickly, so buy well in advance if there's a particular one you want. Accommodation prices also shoot up during peak times – book ahead to avoid disappointment.

2. 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 here at one of the city’s original speakeasies. 

Look for a yellow light to mark 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 an upscale cocktail bar. 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 and Lady Bird to your list. The Drifter is located on the lower level of River North’s iconic Green Door Tavernthe 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.   

3. 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. A wall of washers swings open to reveal a host ready to guide you to an auditorium show or the bar, where the bartenders serve up close-hand magic alongside delicious drinks.

Planning tip: The Magic Lounge hosts a family matinee show every other Sunday that welcomes everyone aged five and up. Perfect for the whole family!

A drummer on stage at Buddy Guy's Legends jazz club in Chicago, Illinois
A drummer on stage at Buddy Guy's Legends jazz club © Marc Lachapelle / 500px

4. Groove to the blues and rock

In Chicago, no genre is as iconic as the blues – the electric blues, to be exact. When Muddy Waters and friends plugged into their amps in the 1950s, guitar grooves reached new decibel levels. Hear it in clubs around town, such as Buddy Guy's Legends, where the icon himself still takes the stage, or Rosa's Lounge, where the vibe is a bit more down and dirty. The blues paved the way for rock and roll, so it's no surprise that cool little clubs hosting edgy indie bands slouch on many a street corner.

5. Shop local in Chicago neighborhoods

Chicago is a collection of vibrant neighborhoods – to really experience the city like a local, go beyond the Loop, avoid Michigan Avenue and support local shops that reflect the city’s make-up. 

Andersonville sits on the North Side and has 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 scene to local hipsters and young families.

If you continue south to Little Village, you'll find a predominantly Mexican community that's the city’s highest shopping district. 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 place Black culture and Black artisans at the forefront.

6. Dine at award-winning restaurants 

Over the years, Chicago's reputation as a culinary destination has flourished. 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, Beard winners and Michelin-starred chefs. Joe Flamm’s Rosemary, an Italian-Croatian restaurant, is one of the city’s hotspots, while Swift & Sons fits the power dining crowd, and Beatrix delivers 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 for the chicken kalamata (a Tina Fey favorite), Oasis in the Loop (located in the back of a jewelry shop) or Aguascalientes in Little Village.    

Best free things to do in Chicago

Cloud Gate (better known as "the Bean") in Millennium Park, Chicago
Cloud Gate (better known as "the Bean") is located in Chicago's Millennium Park © Dan Welldon / Lonely Planet

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 band shell as the sun dips, when 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.

8. Take a tour  

Want to know all the Windy City's secrets? Take a guided tour to uncover lesser-known facts and all sorts of Chicago information that will help you win Trivia Night. 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 the city’s TikTok Historian Shermann “Dilla” Thomas, who leads fascinating walks through Bridgeport/Stockyard, Bronzeville or Pullman/Roseland with his company Chicago Mahogany Tours.

9. 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 and heaps of fringey, provocative "off-Loop" companies, such as The Neo-Futurists.

How to get around Chicago

10. 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-tall Ferris wheel. High-tech rides, splash fountains, big boats and greasy 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.

This article was first published Jun 16, 2021 and updated Aug 9, 2023.

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