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The best things to do on Valentine’s Day

Shake things up on Valentine's Day with a music festival, an ice skating outing or a nearly-nude run
Runners streaked through Wrigleyville in their undergarments during Cupid's Undie Run, February 7, 2015.
Photograph: Max Herman
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Whether you’re single, locked down or questioning your life choices, there are plenty of things to do in Chicago for Valentine's Day. And though the most romantic restaurants in Chicago have plenty to offer, we're challenging you to think outside of the box this year. Sprint around town in your skivvies at Cupid's Undie Run, stuff your face at Chicago Pizza Party, catch award magnet Dear Evan Hansen or dance the day away at Pitchfork's winter music festival. These events make for unique date ideas and awesome solo outings. No matter your relationship status, get out there and do something different for Valentine's Day this year.

RECOMMENDED: Our complete guide to Valentine's Day in Chicago

Valentine’s Day events and concerts

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Cupid's Undie Run 2013
Photograph: Eric H. Brown
Things to do

Cupid’s Undie Run

icon-location-pin Sluggers World Class Sports Bar, Lake View
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Dash through Wrigleyville in your unmentionables to raise dough for the Children’s Tumor Foundation. Participants can raise funds to earn prizes, including shirts, undies and free drinks. There’s also an afterparty at a nearby bar where you can rub shoulders with people who have already seen you half-naked.

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The 2014 Chicago Auto Show at McCormick Place shows off what's new and next in the world of automobiles.
Photograph: Max Herman
Things to do

Chicago Auto Show

icon-location-pin McCormick Place, Museum Campus
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If your special someone loves cars, a ticket to the Chicago Auto Show will do the trick for Valentine's Day. At this annual showcase, close to 1,000 different vehicles will be on display, along with accessories, auto-related exhibits, competition vehicles and collector cars.

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Things to do

Chicago Botanic Garden Orchid Show

icon-location-pin Chicago Botanic Garden | Glencoe, IL, Suburbs
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The orchid is arguably the most romantic flower in the plant kingdom: It's finicky, some varieties require years to bloom and is the most diverse family of flowering plants in existence. See over 10,000 orchids here, and take advantage of the opportunity to purchase one for your sweetheart.

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Theater

Cardboard Piano

icon-location-pin TimeLine Theatre Company, Lake View
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Inside a dark church in northern Uganda, two teenage girls—one a local, the other the daughter of American missionaries—prepare to wed each other in a secret ceremony. Hansol Jung’s gutting drama about love in a time of intolerance receives its Chicago premiere from director Mechelle Moe at Timeline Theatre.

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Kamasi Washington
Photograph: Courtesy the artist
Music, Music festivals

Midwinter

icon-location-pin Art Institute of Chicago | Chicago, IL, Grant Park
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Building on the success of the Pitchfork Music Festival that takes place in Union Park each July, online publisher Pitchfork turns its attention to Chicago's colder months, teaming up with the Art Institute of Chicago to present a new festival. Midwinter takes place amid the museum's galleries and performances spaces, offering three days of live music, amazing exhibits, exclusive compositions commissioned for the event and live artist interviews.

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Dear Evan Hansen
Photograph: Matthew Murphy
Theater, Musicals

Dear Evan Hansen

icon-location-pin James M. Nederlander Theatre, Loop
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The Tony- and Grammy-winning musical makes its monthlong debut in Chicago, unpacking on socially awkward teen's brush with popularity after his classmate commits suicide. 

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Photograph: Courtesy Maggie Daley Park
Things to do, Ice skating

Ice Skating at Maggie Daley Park

icon-location-pin Maggie Daley Park | Chicago, IL, Millennium Park
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Situated in the heart of downtown Chicago, with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a path that's twice the length of a lap around a traditional rink. Admission to the Skating Ribbon is always free, and skate rentals are available.

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Bars

BAITA at Eataly

icon-location-pin Eataly, River North
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Pretend you're vacationing in the Italian Alps at Eataly Chicago's latest pop-up concept, BAITA (pronounced bye-tah). Situated on the store's second floor, the Alpine-themed restaurant is decked out in holiday decor, cozy blankets and fireplaces. The menu includes ski-lodge–approved bites like pillowy gnocchi, melted raclette cheese and Roman-style pizza.

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Photograph: Courtesy of the Estate of Roy Lichtenstein
Things to do

The Naked at the Art Museum Scavenger Hunt

icon-location-pin Art Institute of Chicago | Chicago, IL, Grant Park
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Search out bathing beauties, sultry sirens, a woman enjoying a golden shower from Zeus and more provocative art at this Valentine’s Day scavenger hunt in the Art Institute. You’ll view some of the museum’s best nudes, while learning about art history and enjoying the company of your fellow peeping Toms.

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Anna Karenina
Theater

Anna Karenina

icon-location-pin Auditorium Theatre, Loop
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Russian choreographer Yuri Possokhov stages a world premiere collaboration between the Joffrey and the Australian Ballet. This adaptation of Leo Tolstoy’s classic novel of frustrated love features original music from award-winning composer Ilya Demutsky.

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Theater, Musicals

A Gentleman's Guide to Love and Murder

icon-location-pin Ruth Page Center for the Arts, Rush & Division
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The 2014 Tony Award winner for Best Musical gets its local premiere from Porchlight Theatre. Actor Matt Crowle stars in the role of “The D'Ysquith family,” which is to say that he plays all the people who get murdered. Don’t worry, though—it’s a comedy. And a very funny one at that, with a toe-tapping score that will leave you humming many a murderous melody.

More to explore

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