Millennium Park

Is Millennium Park touristy? Oh yeah. Do Chicagoans still love it? You bet. Millennium Park is such an iconic jewel of downtown, it’s hard to imagine it was once a web of railroad tracks. Not only is it a cultural oasis, it’s also a special events hub, welcoming visitors with free programs, family-friendly happenings, summer concerts, and unforgettable architecture. In the winter, there’s ice skating, in the summer, you can dip your feet in the stream at the Lurie Garden and watch kids play in the Crown Fountain. People picnic on the Great Lawn during a range of performances from the Chicago Symphony Orchestra to St. Vincent, or while partaking in the free Summer Film Series selections.

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You can take a short walk over the BP Bridge to check out the adjacent Maggie Daley Park, a mecca for kids.

Navy Pier

Sorry to break the news, but Navy Pier is the biggest tourist trap in the city. If you’re already here, take a deep breath—it’ll be fine—you’ll just have to be smart about your visit. Lake Michigan provides a spectacular backdrop for the many happenings on the pier, which can range from festivals to fireworks. Since it’s accessible via bus, water taxi, and the Lakefront Trail, Navy Pier attracts a steady stream of tourist traffic. You’ll find everything from the Shakespeare Theatre and Chicago Children’s Museum to Bubba Gump Shrimp and souvenir-stocked shops here. Kids will probably enjoy it, but don’t allocate an entire day for your visit.

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If you’re over the touristy stuff, visit Fish Bar for some great drinks and seafood. It’s locals-approved and run by hotshot chef Michael Kornick.

Photo courtesy of Navy Pier

The Museum of Contemporary Art

Scholars, critics, and hip cats from around the world have tried for generations to answer one simple question: “Is that art?” At the Museum of Contemporary Art in downtown Chicago, that question is finally answered—and the answer is a resounding YES. You never know what you’ll find at the MCA—but whatever it is, it’ll be memorable. The MCA prides itself on being at the cutting edge of the art world, and while it has a large collection of works from 1920 to present, the main draws are its ever-changing installations and guest artist exhibitions. From otherworldly sculptures, to art collective takeovers, to guest bands doing sonic explorations (aka practicing) in the alcoves, there’s always something new. The MCA has a world class reputation and was the only museum in America to host the renowned “David Bowie Is” exhibit in late 2014.

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The MCA has impeccable taste, but that taste might be strong for the average palate. If you’re looking for the old standards, head down to the Art Institute.

The Second City

If an actor on TV has made you laugh any time in the last 50 years, odds are good that that person got their start at The Second City. The oldest and most venerated of Chicago’s many comedy theaters, The Second City brings its world-famous sketch comedy revues to gut-busting life seven days a week. With alumni including Bill Murray, Stephen Colbert, and Tina Fey, The Second City is the marrow of Chicago’s illustrious funny bone. While it’s lost a lot of its bite in the half-century since it opened, it remains a Chicago must-see. There are a number of cabarets and lounges within the Second City complex that house stand-up, independent productions, and student shows, but the historic Mainstage and E.T.C. theaters are what you’re there for. The big theaters also feature a full kitchen and bar, so the drinks keep flowing along with the laughter.

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Comedy doesn’t have MPAA ratings, so expect any children in attendance to learn some fun new words.

Shedd Aquarium

With a collection of over 32,000 animals of the watery persuasion, Shedd Aquarium is a massive indoor kingdom celebrating sea life in all its glory. From wild reefs to touchy-feely stingray pools, prepare to be engaged and amazed. This place isn’t just breathtaking beluga shows. The Shedd has dedicated itself to rescuing and rehabbing aquatic animals while educating the public about endangered species. Not only will the aquarium blow your mind, but your admission fee will also be doing some good for the animal kingdom. The Shedd proudly hosts two million visitors annually, so don’t be surprised if a few dozen people share your sea turtle viewing. Bring the kids, or go it alone to explore at a leisurely place and fully absorb everything the aquarium has to offer.

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Epically long lines, especially during the busy summer months. Purchase your tickets online and arrive early.

River Cruises

When the weather isn’t treacherous and the boats are still in service, there’s no better way to see Chicago than from the river. Traversing downtown through a canyon of towering skyscrapers is highly recommended. While several companies offer tours—Wendella has been doing it since 1935—if you’re interested in the architecture, you may as well get the expert’s perspective on a Chicago Architecture Foundation tour. Otherwise, the Chicago Water Taxi is recommended for a carefree trip.

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Make sure to check the weather and dress appropriately. It can get very breezy on the water—you’re in the Windy City, after all.

Eat Chicago Staples

Chicago is a food city and it always has been. Today, Michelin stars and James Beard winners are peppered amongst the classics. That means deep dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and...Malort, a rather foul liquor that will instantly let locals know “that person’s cool.” Some places to get these staples are more touristy than others, but just ask one local where to go (or read our guides) and you’ll get the real scoop.

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Deep dish pizza is not for the weak. If you eat it, you probably won’t be doing anything with the rest of your day.

Catch a Game

Chicagoans care about their sports. A lot. That passion is what makes going to a game so much fun! Whether it’s the Bears, Cubs, White Sox, or Blackhawks, Chicago fans show up. Our personal recommendation: catch a day game at Wrigley at the beginning or end of the season, when the weather’s not too hot. After the game, celebrate the Cubs victory (or mourn their loss) at the bars around Wrigleyville. There are even some good restaurants in the area now—but a Chicago dog at a Chicago game is really where it’s at.

KEEP IN MIND

Tickets are expensive! You can try to grab some at the last minute for cheap, or just accept that you’re paying an arm and a leg to watch adult men throw a ball.