Chicago. Photo by Shutterstock.

Best Things to Do in Chicago

BY Fifty Grande Editors | January 29, 2021

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Chicago? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Chicago?”

John Hughes movies. Wrigley Field. That bean sculpture thing. Gangsters. Michael Jordan. Based on a handful of common culture points one could mistakenly assume they know all they need to know about Chicago without having spent a minute there. The reality is, it’s a city of neighborhoods and proud communities (they’ll argue about how to pronounce the city’s name), rich with architecture and performance art; a hub for culture and food, street art and comedy. Though people have been leaving in recent years, the Windy City is still one of America’s gems. If you visit today you’re likely to find young entrepreneurs, artist collectives and foodies whose palates extend way beyond marinated meats. Pack an extra jacket—the being brutally cold thing is real—and leave your expectations at the door. Here are the best things to do in Chicago right now. 

But let’s be honest: You’re here for deep-dish pizza

Welcome to a no-holds-barred, meat and cheese extravaganza. Don’t order deep-dish and expect to eat it with your hands, let alone deftly fold it like you can in NYC. You’re in for a hefty, fork-and-knife affair that will leave you rethinking your very definition of pizza. You really can’t go wrong, but here are some of the primo deep-dish purveyors. 

Pequod’s Pizza in Chicago
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Pequod’s Pizza in Chicago

Pequod’s

2207 N Clybourn Ave, Chicago, Illinois, USA

What makes this Lincoln Park staple truly special is the way they let the cheese carmelize around the edge of the pan. It’s not a national brand like Lou’s or Giordano’s, but a superb local favorite. 

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Lou Malnati’s Pizzeria in Chicago
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Lou Malnati’s Pizzeria in Chicago

Lou Malnati’s

1520 North Damen Avenue, Chicago, Illinois, USA

They’re a household name among Chicagoans, and they’ve got locations all over the city and suburbs. But Lou’s maintains their home-cooked style. Want to sample beforehand? They’ll ship anywhere in the U.S. 

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The Art of Pizza in Chicago
#3
The Art of Pizza in Chicago

The Art of Pizza

3033 N Ashland Ave, Chicago, Illinois, USA

This counter-service spot is one of the few places you can get deep-dish by the slice. On top of that, it’s BYOB.

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And don’t leave without sampling Chicago’s Italian beef rendition

This is an Italian-style roll, stuffed with sliced roast beef and either giardiniera (look it up) or sweet peppers. And when Chicagoans do something, they really do it. You say you want a tender, moist beef sandwich? Let me splash au jus on there, or better yet, dunk the whole thing. It’s a meaty indulgence that would give Bill Swerski’s Superfans at least a baker’s dozen heart attacks.

Jonnie’s Beef in Chicago
#4
Jonnie’s Beef in Chicago

Jonnie’s Beef

7500 W North Ave, Elmwood Park, Illinois, USA

Like so many other revelatory roadside eateries, if you blink, you’ll miss it. Widely regarded as the best beef sandwich in Chicago, although that’s a contentious discussion you’re not ready for yet. Just enjoy the beef, Italian ice, and Chicago-style hot dogs. But the line moves fast, so have your order and cash (no cards) ready. 

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Al’s No. 1 Italian Beef in Chicago
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Al’s No. 1 Italian Beef

Al’s No. 1 Italian Beef

548 N Wells St, Chicago, Illinois, USA

The other front-runner for Chicago’s best beef debate. You can order your sandwich “wet” with au jus ladled over it, or “dipped” where they’ll dip the entire sandwich in the pot. 

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Other awesome restaurants

It’s hard to have outdoor hobbies during Chicago’s long Winters, which might explain why the city has such great food.

Girl and the Goat restaurant in Chicago
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Girl and the Goat restaurant in Chicago

Girl and the Goat

809 W Randolph St, Chicago, Illinois, USA

Executive Chef Stephanie Izard is a Chicago native, a Top Chef winner, and the James Beard 2013 Best Chef Great Lakes. Girl and the Goat offers bold, globally-inspired dishes in a homey atmosphere. 

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Parachute restaurant in Chicago
#7
Photo courtesy of Parachute restaurant in Chicago.

Parachute

3472 N Elston Ave, Chicago, Illinois, USA

A stylish, Michelin-starred spot in Avondale that serves expressive Korean-American dishes at reasonable prices. 

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Lula Cafe in Chicago.
#8
Lula Cafe in Chicago.

Lula Cafe

2537 N Kedzie Blvd, Chicago, Illinois, USA

A funky farm-to-table brunch and dinner restaurant that promotes local artists. 

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Alinea
#9
Alinea Google result.

Alinea

1723 N Halsted St, Chicago, Illinois, USA

Alinea’s Google result says it all. This is not an ordinary restaurant. If you’ve got money to blow and by some miracle you get a reservation, this is one of the world’s best. It earned three Michelin stars and the 2016 James Beard Award for Outstanding Restaurant. Chef Grant Achatz’s dishes are truly unique—each one is a full sensory experience.

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Scenic strolls

If the weather’s nice, here are the best routes to admire Chicago’s grandeur and natural surroundings. 

Magnificent Mile in Chicago. Image credit Shutterstock.
#10
Magnificent Mile in Chicago. Image credit Shutterstock.

The Magnificent Mile

Magnificent Mile, Chicago, IL, USA

Impulsive shoppers, beware. A walk down Michigan Avenue will take you past upscale shops, luxury retailers, boutiques and department stores. But it’ll also show off some of the city’s most iconic buildings, like the John Hancock Center, the Chicago Water Tower, the Tribune Building and the Wrigley Building.

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Lakefront Trail in Chicago. Photo by Shutterstock.
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Lakefront Trail in Chicago. Photo by Shutterstock.

Lakefront Trail

Lakefront Trail, Chicago, IL, USA

An 18.5-mile paved trail along the shore of Lake Michigan that goes past Grant Park, Maggie Daley Park, the Museum of Science and Industry, Navy Pier, Soldier Field and several beaches (yes, Chicago has beaches. Yes, you should visit them in the summer). 

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The 606 in Chicago. Photo via Shutterstock.
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The 606 in Chicago. Photo via Shutterstock.

The 606

1805 N Ridgeway Ave, Chicago, Illinois, USA

The Bloomingdale Trail is a reinvented elevated train line that links a network of parks known as The 606. It connects Wicker Park, Bucktown, Logan Square and Humboldt Park—four of the city’s coolest places to hang out.

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Spend a day in these cool nabes

Soaring skyscrapers and busy storefronts are great for a day, but when you want a little more culture, understated charm, and hopping nightlife, here’s where to go.

Logan Square in Chicago. Photo via Shutterstock.
#13
Logan Square in Chicago. Photo via Shutterstock.

Logan Square

Logan Square, Chicago, IL, USA

It’s hip, but not in a “look how cool I am” way, and it’s got a little bit of everything. Longman & Eagle, Bang Bang Pie Shop, and Lula Cafe are must-visits for foodies. And for drinks, grab craft beers at Revolution Brewpub, gin-based cocktails at Scofflaw, or a cozy nightcap at Billy Sunday. Other cool hangouts include Cafe Mustache and Logan Arcade.

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Pilsen in Chicago. Photo via Shutterstock.
#14
Pilsen in Chicago. Photo via Shutterstock.

Pilsen

Pilsen, Chicago, IL, USA

Chicago’s Latin American community is alive and well in this Lower West Side neighborhood. The cantina-styled Caminos de Michoacan is a great stop for Micheladas, and Dusek’s Board and Beer has a fantastic brunch. Plus, Pilsen is one of the city’s most prominent art hubs, featuring the renowned 16th Street Murals and the National Museum of Mexican Art.

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Wicker Park in Chicago. Photo via Shutterstock.
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Chicago, IL, August 19, 2017: Street scene in the trendy, popular Wicker Park neighborhood on a weekend night. Wicker Park attracts many young people because of its vibrant nightlife.

Wicker Park

Wicker Park, Chicago, IL, USA

A hipster haven if there ever was one. Head to Big Star for tacos and a stiff margarita or Irazu for Costa Rican fare. Try The Violet Hour for craft cocktails or the Emporium Arcade Bar for games. To weather cold Winter days, grab a hot chocolate from Mindy’s Bakery or a Nutella latte from Ipsento in neighboring Bucktown.

 

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Street art galore!

Pilsen and Logan Square have long been Chicago’s street art hubs. But like art itself, the scene is always shifting and innovating. Take the B_Line, for instance, a new “street art corridor” in the meatpacking district’s Fulton Market. This series of public art by numerous local artists highlights the city’s diversity and artistic ambition. B_Line feature and local artist CZR PRZ says “There are many incredible POC, women, and LGBTQ artists here that make up a large part of the community.” It’s why we’ve named Chicago as one of the best cities in America for street art

Tour Chicago’s varied architecture from the water

Most of Chicago’s buildings were destroyed in the Great Chicago Fire of 1871, and afterward, a wide variety of architectural styles rose from the ashes. What these buildings lack in history they make up for with creativity and a rare blend of Prairie School, Art Deco, Modernism, Postmodernism and more. The city even has an architectural style named after it: The Chicago School.

Chicago’s First Lady. Photo via Shutterstock.
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Chicago’s First Lady. Photo via Shutterstock.

Chicago’s First Lady

112 E Wacker Dr, Chicago, Illinois, USA

You can admire the city’s various architectural styles by walking around, but if you truly want to appreciate them, an architectural river cruise is the way to go. Float down the Chicago River while learning about each towering building’s architectural influence.

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Ascend one of the nation’s tallest buildings (and argue with locals about the name)

If you’re unfazed by heights or looking to face your fears, you need a trip to the Skydeck atop the Willis Tower. It was once the tallest building in the U.S. before being usurped by NYC’s One World Trade Center and Central Park Tower.

Willis Tower in Chicago. Photo via Shutterstock.
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Willis Tower in Chicago. Photo via Shutterstock.

Willis Tower

233 S Wacker Dr, Chicago, Illinois, USA

Many Chicago residents still cling to the skyscraper’s original name: the Sears Tower (call it that if you want to hide your visitor status). On the 103rd floor, you’ll find an observation deck where you can see all the way to the suburbs and “The Ledge,” a not-for-the-faint-of-heart glass box that lets you look straight down to the street below. 

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Bust a gut at a comedy club

New York City has theatre. L.A. has film. Austin has music. Chicago has those things too, but at its heart, the Windy City is a comedy town. Here are the best places for a laugh.

Second City comedy club in Chicago.
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Second City comedy club in Chicago.

The Second City

The Second City, North Wells Street, Chicago, IL, USA

Look at a list of famous Second City alumni and you’ll find a who’s who of comedic powerhouses, from SNL mainstays to late-night hosts to movie stars. It’s the top tier of America’s improv scene.

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Zanie's in Chicago.
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Zanie's in Chicago.

Zanies

1548 N Wells St, Chicago, Illinois, USA

One of Chicago’s oldest and most popular stand-up joints. On any given night, you might see national headliners or local up and comers.

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Or catch some live music

Comedy is king in Chicago’s entertainment scene, but you can find some top-shelf music venues too.

Soundgarden playing at the Vic Theater.
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CHICAGO, IL - The late singer Chris Cornell performs with Soundgarden during their historic reunion on August 5, 2010 at the Vic Theater in Chicago. Photo via Shutterstock.

Vic Theatre (“The Vic”)

3145 N Sheffield Ave, Chicago, Illinois, USA

A five-story vaudeville house with marble staircases and sculptures on the walls. When it’s not hosting big-name rock bands, it transforms into the Brew & View, a movie theater with three bars.

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Green Mill Cocktail Lounge in Chicago. Photo via Shutterstock.
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Green Mill Cocktail Lounge in Chicago. Photo via Shutterstock.

Green Mill Cocktail Lounge

4802 North Broadway, Chicago, Illinois, USA

This laid-back lounge is known for its jazz and spoken word poetry performances. Al Capone was a regular here and you can even sit in his favorite booth.

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Photo by Clayton Hauck for The Empty Bottle.
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Photo by Clayton Hauck for The Empty Bottle.

Empty Bottle

1035 N Western Ave, Chicago, Illinois, USA

What was once a neighborhood dive bar in the Ukrainian Village has become one of Chicago’s most intimate spots to catch a wide variety of local and touring acts.

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Metro in Chicago.
#23
Metro in Chicago.

Metro

3730 N Clark St, Chicago, Illinois, USA

Located in Wrigleyville, this famed venue has played host to Prince, The Killers, Phish, Kanye West, Chance the Rapper, and plenty more big names. 

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Learn a thing or two at the Museum Campus

This scenic, 57-acre park sits right on Lake Michigan and contains the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History. You could spend a whole day in any one of these three places, so if you’re in town for a while, grab a CityPass, which gives you nine days of entry to these three museums plus Skydeck and the Museum of Science and Industry. You can substitute the Art Institute of Chicago if you’d prefer.

Museum Campus in Chicago. Photo via Shutterstock.
#24
Museum Campus in Chicago. Photo via Shutterstock.

Museum Campus

337 E Randolph St, Chicago, IL, USA
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Cool hotels

After a long day of wandering and deep-dish indulgence, you’re going to want a place to relax. Right this way.

Freehand in Chicago.
#25
Freehand in Chicago.

Freehand Chicago

19 E Ohio St, Chicago, Illinois, USA

Just above the Loop in the cool River North neighborhood, you’ll find this eclectic hostel. It offers cozy rooms and lounge areas, morning pick-ups at Café Integral and evening wind-downs at Broken Shaker. Plus, you’re right next to downtown.

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Hotel Lincoln in Chicago.
#26
Hotel Lincoln in Chicago.

Hotel Lincoln

1816 N Clark St, Chicago, Illinois, USA

Head a little farther north and you’ll hit Lincoln Park, a neighborhood popular with young professionals for its dining, shopping, and proximity to parks. Hotel Lincoln dazzles guests with views of Lake Michigan, a rooftop lounge, and a European-style coffee shop.

Also see: 

Hotel Lincoln

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Found Hotel in Chicago.
#27
Found Hotel in Chicago.

Found Hotel Chicago

613 N Wells St, Chicago, Illinois, USA

You can’t miss this hotel’s cast iron exterior. The interior blends elegance and eccentricity and includes an Asian-inspired bar and karaoke lounge, as well as a restaurant and coffee shop. Another River North establishment, it puts you in the proximity of downtown as well as hip northern neighborhoods.

Also see:

Found Hotel Chicago

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If you have time:

The Bean in Chicago. Photo via Shutterstock.
#28
The Bean in Chicago. Photo via Shutterstock.

The Bean

201 E Randolph St, Chicago, Illinois, USA

Okay, technically it’s called Cloud Gate and it’s a sculpture by British sculptor Sir Anish Kapoor. But everyone calls it The Bean because, well, it looks like a big chrome bean. If you’re so inclined, you can join the throngs of tourists taking selfies in its reflection.

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Wrigley Field in Chicago. Photo via Shutterstock.
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Wrigley Field in Chicago. Photo via Shutterstock.

Wrigley Field

1060 W Addison St, Chicago, Illinois, USA

Baseball fans will want to check out the second-oldest active MLB stadium, complete with its famed ivy outfield walls. The Cubbies have recently shed their “loveable losers” persona and they draw a crowd for most games. Grab an Old Style draft while you’re there, then hit Wrigleyville to party afterward.

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Garfield Park Conservatory in Chicago. Photo credit Shutterstock.
#30
Garfield Park Conservatory in Chicago. Photo credit Shutterstock.

Garfield Park Conservatory

300 N Central Park Ave, Chicago, Illinois, USA

A lush oasis away from the city’s bustle, this 184-acre park is one of the nation’s largest conservatories, exhibiting thousands of plant species. It also includes athletic fields, a swimming pool and spots for fishing.

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