Best Things to Do in Chicago

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. 

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. 

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.

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. 

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. 

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. 

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

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

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.

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.

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). 

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.

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.

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.

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.

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.

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. 

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.

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.

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.

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.

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.

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

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.

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

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

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.

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.

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.