Explore Chicago like a local: here are the 10 best things to do - Lonely Planet (2023)

Whether you're headed to iconic sites like the Bean, the Picasso structure or Navy Pier, or to quieter parts of the city like the North Side’s Andersonville, Chicago keeps the good times rolling.

But with all the experiences on offer, how do you know 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.

Explore Chicago like a local: here are the 10 best things to do - Lonely Planet (1)

1. Attend a game

Chicago's home to the Chicago Cubs (at historic Wrigley Field) and Chicago White Sox (MLB), Chicago Bears (NFL), Chicago Bulls (NBA), Chicago Sky (WNBA), Chicago Blackhawks (NHL), Chicago Fire FC and 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—and maybe even the disappointment—of cheering on the hometown team.

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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 at one of the city’s original speakeasies.

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Look for a yellow light to mark the bar’s entrance – if the light is on, they are 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 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, located in the West Loop. The low-lit bar features live music (jazz, soul and rock) Thursday through Saturday and evokes feelings of 1960s glam.

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3. Find Chicago's magic

Four of the most prominent magicians in the industry reside in Chicago, and Midwest Magicthe world’s largest magic shop – is located in the nearby suburb of Franklin Park. 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.

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Explore Chicago like a local: here are the 10 best things to do - Lonely Planet (2)

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, leave 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 Bucktowntailor 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 shop 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.

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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 Beatrixdelivers top-notch brunch.

For anyone looking to splurge, book a reservation at Next for their Chicago 1933 World’s Fair-inspired meal.

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

Explore Chicago like a local: here are the 10 best things to do - Lonely Planet (3)

7. 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 wine corks pop and gorgeous music fills the twilight air.

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.

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If you want to exploreChicago'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.

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

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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.

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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.

FAQs

What is there to do off the beaten path in Chicago? ›

Top 10 Off The Beaten Path Things To Do In Chicago
  • Visit Treehouse Cat Cafe. ...
  • Take A Trip To Oz. ...
  • Conquer Your Fear Of Heights. ...
  • Check Out Woolly Mammoth Antiques And Oddities. ...
  • Enjoy A Drink At The Violet Hour. ...
  • View A Collection Of Miniature Rooms. ...
  • Check Out The Wabash Art Corridor. ...
  • Visit The World's Largest Tiffany Glass Dome.
1 Nov 2021

What is Chicago's most famous dish? ›

If there's one Chicago food that's the best known, it's deep-dish pizza. Composed of a thick crust, zesty tomato sauce, personalized toppings and a behemoth layer of cheese, the Chicago deep-dish dares to be different.

What is the most popular dish from Chicago? ›

1. Deep-Dish Pizza. You can't talk about iconic Chicago cuisine without including deep-dish pizza. Although thin crust pizza certainly has its place in the Windy City, deep-dish pizza and Chicago have become nearly synonymous.

Is 2 days enough in Chicago? ›

Short answer – no – there is soooooo much to do and see in the city that 2 days in Chicago won't even come close to enough to see it all! However, I have found that 2 days in Chicago is definitely more than enough time to see all the highlights and to get a good introduction to the city.

How many days is enough to see Chicago? ›

3-5 days is enough time to visit Chicago. For seeing the top tourist attractions and exploring some different areas, 3 days in Chicago is enough, just know your days will be packed. If you want a slightly slower-paced trip, 5 days will provide extra leisure time.

Is 3 days enough to visit Chicago? ›

There is so much to do in Chicago but three days is enough to see most of Chicago's top attractions. I have grouped each day by neighborhood so you don't have to waste a lot of time getting around.

What is Chicago's famous for? ›

Some of the many things Chicago is famous for are: Chicago-style hot dogs, Chicago-style (deep dish) pizza, Maxwell Street Polish Sausage, jazz music, and 1920s gangsters, for example Al Capone. Chicago is also known for architecture, for example the Sears Tower and museums. It is also known for its loyal sports fans.

What is the prettiest part of Chicago? ›

Old Town and River North are considered two of the prettiest neighborhoods to live in but for vastly different reasons. Let's see how these two gorgeous downtown Chicago communities compare.

What part of Chicago is good for tourists? ›

The best location to stay in Chicago, especially for first-time visitors, is the Loop, popularly referred to as Chicago Downtown or Chicago Loop. Located at the center of town, the Loop is where everything happens, and you can easily navigate your way to other parts of the city from there.

What is the most visited place in Illinois? ›

Chicago is the state's most popular destination, drawing travelers from across America and around the world. This is where you'll find some of the state's best retail options, restaurants, museums, and cultural venues.

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