What are the best things to do in Chicago?

Answers from Our Experts (13)

As one of the United States’ top travel destinations, Chicago is teeming with things to see and do. Whether you’re in the busy downtown amid stunning skyscrapers or visiting one of the city’s many culturally rich neighborhoods, there are an overwhelming amount of attractions. Our Forbes Travel Guide editors recommend putting these five spots on your Chi-Town itinerary:

1. Millennium Park. When Millennium Park opened in Chicago in summer 2004, it was several years overdue and millions of dollars over budget. But for Chicagoans, it’s hard to stay mad about the delays and cost after seeing the park’s tremendous role as a civic center. Now, tourists and locals mix and mingle over the park’s weekly concerts (many of them free) as well as public art exhibitions and expos. The downtown park is also home to the lovely, peace-inducing Lurie Garden; the interactive, wet-and-wild Crown Fountain; and everyone’s favorite reflective bean-shaped sculpture, Cloud Gate.

2. Public art. If you can’t get enough of the Bean — locals’ nickname for Cloud Gate — check out Chicago’s plentiful public art beyond the confines of Millennium Park. A walk in the Loop or Chicago’s neighborhoods showcases the citywide outdoor museum. The West Loop has The Haymarket Memorial on Desplaines Street between Lake and Randolph streets, and the South Loop has Arris at Cermak Road and Calumet Avenue. Even the El can bring you closer to public art: Many of the city’s CTA stations feature mosaic murals and pieces by local artists, such as Juan Chavez and Corinne Peterson’s Hopes and Dreams (Red Line Roosevelt station, South Loop).

3. Architecture. Other cities might vie for the title of skyscraper capital of the country, but the truth is, these awe-inspiring structures were invented in the Windy City at the turn of the century, after the Chicago Fire. If you’re mad for Mies (van der Rohe, that is), just walk through Chicago’s Loop and look up; or take a ride on the Chicago History Museum’s Architecture River Cruise, which winds through the Chicago River and gives you a rundown of the city’s most significant buildings.

4. Willis Tower. To really get an aerial appreciation for Chicago’s stunning architecture, visit one of its sky-high buildings. From the observation deck at the 103rd floor of the Willis Tower, formerly the Sears Tower, you can see up to 40 miles out in either direction on a clear day. The John Hancock Observatory is no slouch, either. Take the elevator to the 95th floor Signature Room Lounge, where you can get vistas for the cost of a slightly sugary cocktail. (Ladies, check out the view from the bathroom.)

5. Art Institute. You’ve seen Ferris Bueller’s Day Off and the spoofs of the farmer couple in the American Gothic painting — now experience the Art Institute of Chicago in the flesh. The Renzo Piano-designed Modern Wing, opened in 2009, is simply stunning and one of the city’s best recent attractions. Whatever you do, set aside an afternoon to take in this massive museum, which boasts an impressive collection of Impressionist and post-Impressionist pieces, plus 20th-century classics.

Michael D. Solis

Our five top things to do in Chicago are visiting Navy Pier, shopping on Michigan Avenue and Oak Street, taking an architectural boat tour, heading up to Wrigley Field, and eating at Chicago’s world-class restaurants.

I don’t have a car, so I’m a big bike rider. Chicago is definitely a city of neighborhoods and compared to cities of its size —say, New York or L.A. — I find it a much easier and more bike-friendly city. With L.A., it’s so spread out, and with New York, you’ve got so many bridges, where Chicago is a little bit kind of more compact. That’s a great way to get around and see the city. I love Millennium Park. I think when that opened Chicago really went to world-class-city level with that kind of public space right along the lake. And certainly the lake; it’s amazing how much it’s just like the ocean but just without the salt. You’ve got these beautiful white-sand beaches and waves, and you can’t see across, so it’s hard to imagine that it’s a lake.

And then in the summertime, I think it’s like one of the most beautiful cities anywhere. The weather’s got its moments — when there’s snow on the ground, it’s absolutely stunning. The sleet in between is not so much fun, but I think everyone in Chicago kind of deals with that because they know in the summer it’s a really priceless city to be in.

Just going out to eat and simply going to the dog park with my dog. It’s just a really comfortable living city.

Definitely take an architectural tour on the river. Visit some of the Chicago museums — they are some of the best in the world. Chicago celebrates sports better than anyone — there’s nothing like a Cubs baseball game or White Sox game or Chicago Bears game. Even though they may not win, you’ll have an amazing time. If you’re an athletic type or want to just take a walk, there’s nothing more beautiful than walking along the lake on Lakeshore Drive in the parks [Millennium, Grant and Lincoln]. Chicago has such diversity in its neighborhoods and they’re so close together that you don’t have to deal with traffic — I think just explore some of the neighborhoods because they are all so unique and different. Our Chinatown isn’t as big as New York’s, but it’s just the right size and has amazing food. And in New Chinatown [on the north side], you can get a fantastic bowl of pho, or you can go up to Andersonville and discover some great Middle Eastern dishes.

I would say our lakefront is unsurpassed in beauty, so I love that in the summertime, especially. We don’t live too far from the beach. We have this huge lakefront with walking trails and paths, so my husband and I like to take the dog for a walk and enjoy the lake. Chicago goes a little crazy here in the summertime because our winters are so bad, so we try to take every advantage of the lakefront as much as we can because you know you’re going to be locked away for six months in the winter. I love our lakefront; it’s awesome.

Obviously just checking out other restaurants. I think our dining scene here is awesome, and we’ve been opening some really interesting places lately, especially in like Logan Square, like Matthias [Merges]’ Yusho. There’s always a new restaurant to go visit. I like to support other restaurants as much as possible, and just go check them out and support business and kind of see what’s going on in the city. I definitely love visiting the restaurants in Chicago.

Art museums and plays, the theater. We’ve had this extraordinary run with Broadway here in Chicago with The Book of Mormon right now. And with the Lookingglass, Steppenwolf and The Goodman, there’s always an awesome play to go check out. The theater scene here is just amazing. My husband is a writer, so we always like to catch a play.  We try to do that whenever possible, especially during the colder months. I think there’s something about going to see a play, hiding away in the dark and seeing drama unfold before you.  We’re very fortunate to have such a vibrant theater scene in the city.

Wrigley Field — you’ve got to go to Wrigley Field. I’m a huge Cubs fans; it’s awesome. I think that Millennium Park is super cool. The museums are awesome.

I think that Chicago has the best restaurant scene in America. When you look at the three cities that could all vie for that number one spot — San Francisco, New York, Chicago — and how they’re all different, I just think Chicago is better at the hospitality aspect. I think all three of those cities have amazing restaurants. I think that we’re the best at the way we treat people.

I love all of the architecture in the city. I think it’s the most gorgeous skyline of any city; so just walk around, take a boat tour or look at the architecture.

I love taking people to Devon Street because I love the variety of shops and restaurants. You can go to India Sari Palace to get saris or you can get henna done or fresh coconut or fresh pomegranate juice. What’s special about Chicago is all of its really cool ethnic pockets, and I love to take people to see that. On Broadway and Argyle Street, there’s a place [Ba Le] that sells Vietnamese sandwiches. Those sandwiches are amazing.

Lake Michigan is really nice; it always seems to be a bit crowded. It’s really nice if you go south of the city center where it’s beautiful and there’s less density of people.

If you’re a first-timer in Chicago, go to the lakefront; go to Millennium Park. You have all the outdoor sculptures and the backdrop of all the skyscrapers. If you don’t get to go up Willis Tower, you can see it by walking around the Loop. See the food scene in some areas, like Michigan Avenue. I think most people don’t make it up to other neighborhoods like Andersonville. It’s great for families instead of staying downtown.

I wish I spent more time seeing and doing stuff. I love just walking through Millennium Park. Also in Uptown, dashing through the Southeast Asia section in there. Just getting pho and checking out the little Asian pastry shops and stuff like that — that’s a blast. Hipster-watching in Bucktown.

[Chicago’s] a great place for just being outside in the summertime — finding a friend with a rooftop or a nice big deck and grilling out — that’s what Chicago’s all about. It’s the nicest thing here. Getting out on the lake. If you can sucker someone with a boat into getting you out on the lake, that’s really great.

We have incredible architecture here, so you can kind of just walk around. But you have to look up. There’s a lot of fascinating relief work on the buildings. People just aren’t building things like that anymore. There’s also a lot of modern architecture here, with the influence of Mies van der Rohe coming from Germany from the Bauhaus after World War II. There’s just a huge amount of fascinating buildings to look at. The buildings are not all together; some are clustered. We have Frank Lloyd Wright’s works. You can go see some of his architecture in Oak Park; it’s just a train ride away. There’s a lot of really fascinating architecture.

We also have this public lakefront. You cannot purchase lakefront property here; it’s for the public. It runs from the south edge of downtown all the way up to practically the city boundary with Evanston. There are bike trails and an aviary. There’s all this really beautiful stuff; there’s public beaches, parks. It’s pretty cool.

I think the restaurant scene here is pretty profound and varied now. In the past 10 years, I’ve just seen incredible growth. You can get anything from a very exclusive experience at Alinea down to a workingman’s bar where you can get Pabst Blue Ribbon and a shot.

Chicago has so many professional sports teams, so a game is a must. We also have an amazing art scene. I personally enjoy the Museum of Contemporary Art Chicago and The Art Institute of Chicago. For theater, there’s Steppenwolf Theatre Company and Goodman Theatre. And you need to eat in this city because of its vast diversity. Standouts include progressive grunge restaurants like Schwa, celebrity-chef driven restaurants like Rick Bayless’s Frontera Grill and Topolobampo, or amazing ethnic cuisine like Tac Quick Thai Kitchen and Katsu. You should also explore Chicago’s beautiful beachfronts and parks.

Lauren Viera

One of my all-time favorite things to do in Chicago is to book a ticket with the Chicago Architecture Foundation’s Architecture River Cruise. In a boat that’s just the right size (big enough not to rock, small enough to feel like you’re not one in a herd), you’re invited to pull up a chair on the top deck and take in the sights while a non-hokey architectural docent points out Chicago’s most beautiful architecture.

Beyond that, I always encourage visitors to check out Millennium Park, even if they’re just passing through on their way to the Art Institute of Chicago (another one of the best things to experience in town). No matter what time of year you’re visiting, there’s something happening in this giant park that’s considered Chicago’s front yard—from free summer concerts in the Frank Gehry–designed outdoor amphitheater, to caroling and ice skating during the wintertime.

Finally, two of the best things to do here are to eat and drink. Chicago’s dining and drinking scenes have both skyrocketed in the past decade, positioning many Chicago chefs at international caliber. All but a handful of top restaurants save some tables for walk-ins, and especially if you happen to stop by at an off-peak time, you might get lucky. Save room for after-dinner drinks: Chicago’s cocktail scene is having a moment, and there are dozens of venues around town whose bartenders love showing off.

Related Questions