Chicago, Illinois, is a vibrant and diverse city known for its spectacular restaurants, world-class architecture, legendary sports teams, and famous comedy clubs. But as the third largest city in the United States, there are tons of great things to do in Chicago and it can be hard to figure out how best to spend your time. Luckily, this guide spotlights the 9 best places to visit in Chicago – so if you’re wondering if you should visit Chicago (spoiler alert: you absolutely should!), read on for our tips and suggestions!
9 Best Things to do in Chicago, Illinois
Take an Architecture Cruise
Chicago is one of the greatest cities in the world for architecture. In 1885, the world’s first skyscraper was built in downtown Chicago. At 10 stories tall, the Home Insurance Building would be completely unremarkable today, but at the time it was big news. 90 years later, the Sears Tower (now Willis Tower) was built just two blocks away from that original skyscraper and won the designation of being the tallest building in the world, a title it held for nearly a quarter of a century.
One of the best ways to experience Chicago’s world-class architecture is on a Chicago Architecture Center River Cruise, a 90-minute fact-packed boat ride along the Chicago River and one of the top Chicago attractions. Led by an architecture expert, you’ll discover the secrets behind some of the city’s most iconic buildings like the Tribune Tower, Merchandise Mart, the Wrigley Building, and the “corn cob” Marina City towers. The cruise is also offered in the evening and is one of the best ways to see all the gorgeous, glittering Chicago attractions at night.
Eat a Real Chicago-Style Pizza
Eating a slice of pizza is practically a rite of passage for anyone visiting Chicago. But did you know there’s more to Chicago pizza than its famous deep dish pie? To truly eat like a Chicago local, order a tavern-style pizza – the crust is thin and crispy with a light dusting of cornmeal on the bottom, the sauce is often on the sweeter side, and the slices are cut into small squares. Try Pat’s in the Lincoln Park neighborhood, Michael’s in the Uptown area, and our pick for one of the best-named restaurants, Pizza Fried Chicken Ice Cream in the Bridgeport section of the city.
Speaking of Chicago-style food: curious about what goes on a Chicago-style hot dog? While you can certainly order your dog with any topping combination that suits your taste, an “official” Chicago-style hot dog comes on a poppy seed bun and is topped with yellow mustard, white onions, sweet pickle relish, tomatoes, a dill pickle, pickled sport peppers, and a dash of celery salt. You can have ketchup if you ask for it, but you might get some funny looks.
Visit the National Museum of Mexican American Art
Visiting an art museum is one of the best things to do on your Chicago vacation. But with tons of different options, it can be hard to know which is the best museum in Chicago for you. Popular art museums like the Art Institute and Museum of Contemporary Art are certainly worth a visit, but they are quite large and can quickly get crowded. For a unique experience, visit the National Museum of Mexican Art, where you can see over 18,000 pieces of textiles, folk art, and other work that celebrates Mexican art and culture from both sides of the border.
Keep the art party going – the museum is located in Chicago’s Pilsen neighborhood, a historically Mexican-American community and where you can view a stunning array of public art that pays homage to the Mexican muralist movement. You can spot the murals all over the neighborhood, but two spots to check out are 18th Street between Loomis and Paulina for giant building murals, and 16th street from Halsted to Western Avenue for a nearly 2-mile long canvas along the 16th Street Railroad Embankment.
See the Views from the Lakefront Trail
A walk along shimmering Lake Michigan is one of the best things to do in Chicago. And thanks to the Lakefront Trail, you can turn off your GPS and focus on the scenery ahead of you. Paralleling the lake for 18.5 stunning miles, this trail is loved by tourists and locals alike who run, walk, or bike along the completely paved road. Don’t have time for the entire path? Start at the northern trailhead and walk south for about two miles until you hit Montrose Beach, where the views of the skyline will be postcard-perfect. And while you’re there, check out the Montrose Point Bird Sanctuary, a stretch of land that’s internationally recognized for its high number of migratory birds. And if you’re new to birdwatching or want to brush up on your birding lingo before visiting the Sanctuary, check out our beginner’s guide to birdwatching!
If you’re looking to explore the city on two wheels, Divvy is Chicago’s bikeshare program. With hundreds of docking stations all over the city, it’s a convenient, affordable, and sustainable way to see the sights!
Get Family Friendly on the Museum Campus
Traveling with the whole family? You’re in luck! Chicago is one of the best places to visit with kids of any age. You’ll want to head to Museum Campus, a 57-acre park that holds three of the best museums in Chicago dedicated to the natural sciences. The Field Museum is a natural history museum and has a massive collection of artifacts and specimens, including “Sue,” one of the largest and most complete T-rex skeletons ever discovered. The Adler Planetarium is your home for all things beyond the stratosphere, with exhibits on space exploration and a giant dome theater that offers a rotating selection of sky shows. And for all the budding oceanographers out there, the Shedd Aquarium is an animal care research facility with living reefs, adorable penguins, and a truly stunning oceanarium that overlooks Lake Michigan. Do know that each museum is big, however – you definitely shouldn’t try to tackle more than one per day!
Explore the 606 Trail
If you’re wondering what to do in Chicago, consider exploring the city beyond the downtown tourist center. 77 different neighborhoods make up the city of Chicago, each with its own rich history and culture. One of the best ways to experience four different neighborhoods at once is on the 606 Trail, a 2.7-mile elevated path that runs along unused railroad tracks. It’s the longest greenway project of an old rail line in the United States and snakes through northwest Chicago’s Wicker Park, Bucktown, Humboldt Park, and Logan Square neighborhoods. Walk, run, or bike along the path, and explore the parks, scenic lookouts, and public art installations located throughout the trail.
Fun fact: the 606 Trail gets its name from the first three numbers that begin most Chicago zip codes!
Water Sports on the Chicago River
Spending an afternoon exploring the Chicago River is one of the most fun things to do in Chicago. At 156 miles long, it flows north and southwest throughout much of the city before running right through the heart of downtown in a system of picturesque canals. But the Chicago River is often overshadowed by its much (much) bigger aquatic sibling, Lake Michigan. Good things come in small packages, however and the river’s calm waters make for great water sports! Kayak Chicago rents single and double kayaks, stand-up paddleboards, and electric paddle boats by the hour, and offers paddling instruction, SUP yoga classes, and guided tours if you want to leave the navigation to someone else. Need an excuse to buy a new bathing suit? Check out our guide to the best sustainable swimwear brands!
Visit a Botanical Garden
If the wind chill in Chicago is getting a little too harsh for you, there’s no better place to warm up than in a climate-controlled greenhouse! Depending on which part of the city you’re staying in, you’ll have a lot of different gardens and conservatories to choose from. The Lincoln Park Conservatory has a traditional Victorian-era glasshouse that floods with natural light and features an 1892 Palm Tree House that is one of the top Chicago tourist attractions. Head west of downtown for the Garfield Park Conservatory, which is one of the largest botanical conservatories in the country and houses thousands of plant species in themed rooms like the Desert House, Fern Room, and Aroid House. And if you need an excuse to explore the northern suburbs, the Chicago Botanic Gardens are set on 385 acres of sprawling grounds and offer dozens of distinct and interactive garden habitats, from edible plants to a hands-on teaching garden.
Take a Day Trip to a National Park
You’ll need to head out of town for this one, but as one of the only National Parks in the midwest, the Indiana Dunes National Park is well worth a side trip during your Chicago vacation. When the glaciers retreated at the end of the Ice Age, they left behind the landscape that forms the present-day Great Lakes Region. One of the results of those receding glaciers are giant sand dunes that lie at the southern tip of Lake Michigan. At only 23.5 square miles, Indiana Dunes is one of the smaller national parks in the country, but it packs an ecological punch by offering access to swamps, bogs, prairies, and forests, as well as 15 miles of beaches and Lake Michigan shoreline. Swimming and relaxing on the sand are two of the most popular activities in the park, but there are also ample opportunities for hiking, biking, and bird watching.
No car? No problem! Take the South Shore Line, a Northern Indiana Commuter train, to Dune Park Station. Many of the park’s most scenic beaches and trails are a short walk away!
Get Excited for the Obama Presidential Center
Put this on your radar: When the Obama Presidential Center opens in 2025, it is going to be gorgeous. Celebrating America’s first African American President and First Lady, the 20-acre campus on Chicago’s South Side will be the ultimate gathering place for residents of the Jackson Park neighborhood where Barack and Michelle Obama used to live. With a museum, public collaborative spaces, an outdoor plaza and performance space, and a new branch of the Chicago Public Library with a rooftop garden and apiary, this community hub will create thousands of local jobs and drive the area’s economic potential. There will also be a park surrounding the Center with year-round play areas, a walking path and pedestrian promenade, a great lawn, and a rec center with plenty of basketball courts.
Tips for Visiting Chicago
Where to Stay in Chicago
There are thousands of hotels in the Chicago area to choose from, so how about a stay at The Gray! With electric vehicle charging stations, refillable bathroom amenity containers, and a partnership with a nonprofit to recycle unused portions of bar soaps, this is one of the most sustainable hotels in Chicago. If you already have other accommodations, then check out Boleo, The Gray’s rooftop restaurant and lounge, which sources from local food purveyors to reduce carbon emissions from long-haul travel.
How to Get Around Chicago
The “L train”, short for “elevated train,” is Chicago’s public transportation system and a safe, convenient, and sustainable way to get around the city. You can pay-as-you-go, but the most affordable option is to purchase an unlimited pass, available in 1, 3, or 7-day timeframes. The eight different L lines are differentiated by colors, and nearly all of them branch out from Chicago’s downtown Loop neighborhood.
Chicagoans use the cardinal directions to refer to locations throughout the city, but you won’t hear anyone talking about something on the “east side” – that’s Lake Michigan! Also keep in mind that while the actual city of Chicago has definitive boundaries, the “Chicagoland area” does not and as a result, is BIG. Since there are no geographical barriers like mountains or major rivers to contain the urban sprawl, “Chicago” as a general location can often refer to anything that’s as far north as the Wisconsin border and as far south as the border of Indiana.
When to go to Chicago
Chicagoans like to say that if you don’t like the weather, wait five minutes and it’ll change. Chicagoans also like to say that if you visit Chicago, you might get lucky and experience all four seasons in one day. It might seem like overkill to have two different common phrases regarding the weather in one specific city, but that just indicates how seriously Chicagoans take their weather. And for good reason – winters in Chicago can be brutally cold, and you’ll want to stick to indoor activities if you visit the city between January and March. If your schedule allows, visit Chicago in the spring to see parks and gardens in bloom, in the summer for epic festivals like Taste of Chicago and Lollapalooza, in the fall for warm weather without the humidity, and in November and December for cheery holiday markets and a Festival of Lights along the Magnificent Mile.
