Whether you’re here for a weekend or here for a lifetime, there are certain Chicago activities and institutions you can’t not experience during your time in the city.
The best thing about our glorious Midwestern gem of a town is that there truly, really is something for everyone here—from sports fans to foodies to culture hunters to music lovers.
You could spend years trying to tap into the best things to do in Chicago and still not scratch the surface, but we’ve narrowed it down to a (somewhat) manageable list. Do your best to check everything off and then do some of your own exploring! We promise you won’t be let down.
Sportsball
Cubs. White Sox. Bulls. Bears. Blackhawks. Fire. Sky. We won’t persuade you to form preferences just so long as you’re rooting for the local team. Your Chicago bucket list isn’t complete until you’ve caught a game from each of our sports teams. Find out what’s in season here.
Museums
If there’s one thing Chicago isn’t short on, it’s world-class museums. Seriously, we forget how lucky we are sometimes. Explore the sea, space and scenes from the past all in one stop at Chicago’s Museum Campus, home to Shedd Aquarium, Adler Planetarium and the Field Museum. Of course, your tour of Chicago’s museums isn’t complete without a trip further south to the Museum of Science & Industry. You can even score free admission on some days!
Photo via Facebook/Vienna Beef
Hot Dogs, Italian Beef & Deep Dish Pizza
One of the hottest debates in the city is where to find the best Chicago food staples—hot dogs, Italian beef and deep dish pizza. While we can’t come to an official consensus, locals can tell you which places come close. Here are our picks for best hot dogs around town, craziest Chicago pizza creations and top-notch Italian beef.
The Magnificent Mile & Millennium Park
You can’t come to Chicago without doing a little splurging—or just a bit of window shopping. Take a walk down The Magnificient Mile to see all your favorite stores in one place. If you keep walking down Michigan Avenue, you’ll make it to Millenium Park where you can take your obligatory Bean selfie, splash around in Crown Fountain (the one with the faces on it), admire Lurie Garden and in the summer catch an outdoor show at the Jay Pritzker Pavillion.
Photo via Facebook/Chicago Water Taxi
Water Taxis & Chinatown
There’s nothing like beating Chicago traffic by way of boat. That’s right. The Chicago River Water Taxi will take you from The Loop to Chinatown where you can explore the shops, restaurants and more in one of Chicago's most ethnically rich neighborhoods. Find some of the best dumplings in Chicago while you're there.
Photo via Facebook/Goose Island
Locally Crafted Drinks
It’s no secret that Chicagoans enjoy their alcoholic beverages. We like them so much so that we’ve gotten quite fond of making our own. Spend a day touring and drinking at one of our awesome breweries like Goose Island Beer Company, Lagunitas Brewing Company or Half Acre Beer Company. If you want the hard stuff, explore Koval or Rhine Hall distilleries for a bit of locally made, A-grade whiskey and brandy, respectively. Find a full list of Chicago-area breweries and distilleries here.
Photo via Facebook/Skydeck Chicago
Sky High Views
Many locals will tell you that the best view of Chicago is 90+ floors up at the 875 N. Michigan Ave. building (formerly the John Hancock Center). The Signature Room on the 95th floor is a beautiful place to raise a glass of champagne and stare out over the city or get a more expansive view of the skyline at 360 Chicago one floor down. (Don’t worry, there’s a bar there, too.) Across town, you can look straight down at the city from 1,353 feet in the air at the Willis Tower Skydeck.
If you’re looking for other options, there are plenty of rooftop bars scattered across the city.
History Lessons
Make a stop at the Chicago History Museum in Lincoln Park for a glimpse into our city’s 200+-year past. You’ll learn a bit about Chicago’s politics, culture, architecture, music and even food, all from a historical standpoint.
If you want to immerse yourself even further, take a tour of the city by boat or bus. Soak up the beauty of Chicago’s architecture and learn something along the way. Try Weird Chicago if you’re more interested in ghosts and gangsters. We also recommend Free Tours By Foot for a variety of tour topics.
Photo via Facebook/Buddy Guy's Legends
Jazz & Blues Clubs
Chicago’s relationship with jazz and blues music is as old as the city itself. Some of its most iconic hangouts are also legendary music clubs. For jazz, we recommend familiarizing yourself with The Green Mill in Uptown (where Al Capone was once a regular), Jazz Showcase in South Loop and Andy’s Jazz Club in the heart of River North. Blues fans should definitely check out nightly performances at Buddy Guy’s Legends, Kingston Mines, B.L.U.E.S. and Rosa’s Lounge.
Photo via Facebook/Alinea
Michelin-Starred Meals
It’s hard to walk down a single block in any neighborhood of Chicago without stumbling into an amazing restaurant. Chefs flock from all over to open kitchens here so it’s no surprise that we’re now home to more than a dozen Michelin-starred menus throughout the city. Make this your most delicious bucket list.
Beaches
They don’t call us the Third Coast for nothin’. Chicago’s beaches are a commonly overlooked highlight of the city. Stretching from the north to south sides of the city, they make for a great way to take advantage of our cherished summer months and soak up some sun in the sand. Find some of our favorites here.
If you’re reading this while it’s snowing outside, there are still great opportunities for good lakefront views in the cold weather! Go snap something for your Instagram feed along the Museum Campus just south of downtown or at Promontory Point on the South Side.
Photo via Facebook/The Owl
4 A.M. Bars
You haven’t truly experienced Chicago’s bar scene until you’ve experienced it until 4 o’clock in the morning (5 o’clock on Saturday nights)! Not every bar in town has a 4 a.m. liquor license (most can only serve until 2 a.m.), but we hold near and dear the ones that let us make bad decisions late into the night. Here are our favorite places to stay out too late at.
Tastes From Around The World
Like many cities, a handful of Chicago neighborhoods have more of a specific cultural tie than others. If you’re looking for a specific type of food, we know where to send you for a little neighborhood pride and a lot of flavor.
Chinatown is an obvious choice for Chinese classics like dim sum. Greektown just west of the Loop is your best bet for, well, you guessed it. On Chicago’s North Side, you can find amazing Indian food along Devon Avenue in Rogers Park and tasty Vietnamese bakeries up and down Argyle Street in Uptown. Humboldt Park is the birthplace of the Jibarito sandwich (steak, cheese, lettuce, tomato and garlic mayo sandwiched between two fried green plantains) and home to other amazing Puerto Rican fare. Pilsen is your go-to neighborhood for tacos and other Mexican dishes. Find some of the oldest and best Italian food in the city along Taylor Street in Little Italy. Simply in need of some comfort food? Find some of the best Southern-inspired menus on Chicago’s South Side. Are you full yet?
Photo via Facebook/Urban Kayaks
Kayaks & Canoes On The River
Want a workout and a chance to see Chicago’s many waterfronts? Rent a kayak. You’ll be able to get your splash on in a kayak from Wateriders or Urban Kayaks. This will give you an amazing and tranquil view of the amazing downtown architecture. If you’re trying to escape the urban jungle, just head north to Lakeview and get in the river at Chicago Canoe and Kayak.
The Riverwalk
Chicago’s Riverwalk truly isn’t acknowledged enough. Between art and entertainment series like the Merchandise Mart’s Art On The Mart and a bevy of food and drink options, it’s a fantastic place for your next adventure during the warm months. Even before things heat up, you can still enjoy riverside views from City Winery’s heated domes. Find a full list of dining options, activities and events here.
Art Galleries & Museums
Modern, classical, local, international. Chicago’s art scene encompasses dozens of museums and galleries all over town. Of course, your journey should probably start with obvious picks like the Museum of Contemporary Art and the Art Institute. Once you’ve checked those big ones off your list, explore some of the multicultural offerings in town like the National Museum of Mexican Art. Chicago universities Loyola and DePaul also house art galleries if you want to check the up-and-coming talent in town.
A Legendary Comedy Scene
We may be the “Second City” but Chicago is home to a first-rate comedy scene with performances for everyone. The Second City, Laugh Factory and Zanies Comedy Club have all helped foster the careers of famous comedians. (We’ll skip the name-dropping for now). If just watching doesn’t tickle your funny bone, get involved by taking one of the many comedy classes offered at The Annoyance Theatre.
Photo via Facebook/Steppenwolf Theatre
Local Theatre
New York City isn’t the only city in the States with an amazing local theatre scene—not even close. Chicago is home to dozens of production companies and theatres that keep our calendars full year-round. Broadway In Chicago is the source for many of the mainstream touring shows like Hamilton that make their ways through Chicago. You can also attend shows at Steppenwolf and Goodman theatres for dynamic storytelling and world-class acting. Check out Hell In A Handbag’s calendar for LGBTQ+-friendly parodies and stylistically campy productions sure to leave you with a smile.
Photo via Facebook/The 606
The 606
Running from Humboldt Park to Avenue, The 606 bike and walking path gives you easy access to Wicker Park and surrounding areas with stop-offs every few blocks between. The elevated pathway provides beautiful views of some of Chicago’s most vibrant neighborhoods, parks and restaurants. With constant landscaping, art installations, and plans for expansion, the 606 is certain to be a Chicago gem for years to come. Check the website for news and a full map.
Photo via Facebook/Chicago Thanksgiving Parade
Parades
The Chicago calendar is packed with parades year-round. During the holidays take your family down to State Street for the annual Thanksgiving parade and Magnificent Mile Lights Festival. Celebrate the many cultures within our city at The Mexican Independence Parade during the fall, The Chinese Lunar New Year Parade during the winter or Puerto Rican People's Day Parade and the Bud Billiken Parade during the summer. Support the LGBTQ+ community at the Gay Pride Parade every June. Whatever time of the year you decide to attend a parade just know it will be a party!
