Dating in Chicago offers its many perks. You can indulge in the pulse of urban living, escape from the rush of city life, or find a happy medium between the two. Whether you’re looking for ideas for a first date or need a rekindling rendezvous with your long-term lover, Chicago is up for the challenge.
ARTSY vibes
Pilsen is the shining ode to Mexican-American culture in Chicago and one can argue that its most luminous star is the National Museum of Mexican Art. Showcasing art from both sides of the border, this immersive experience is ripe for first dates and for more seasoned couples too. Saunter hand-in-hand as you peruse the rich textile collection or oggle over Día de Muertos artifacts. With free admission everyday, you can save your coin for the local taco truck right down the street. Art, tacos, and love. This babe’s in.
RETRO / SULTRY vibes:
Humboldt Park’s California Clipper is a landmark live music venue with retro vibes and divey digs. Sit back in a spacious booth and take a trip back to the 1940s as a local Chicago band serenades on stage. On Tuesdays, catch a live burlesque show–a true testament to vaudeville performance. There’s also a good chunk of time between acts — perfect time to whisper dirty little details to your lover.
CEREBRAL vibes:
If getting lost in a meandering path of towering books is your idea of a perfect date, Wicker Park’s Myopic Bookstore is the perfect literary labyrinth. With no wifi in range, you can connect with your partner as you compare favorites and venture into categories anew. Sneak a kiss between reads and then head down the street to the Robey for drinks while you muse over the ramblings of Rumi.
LUSH / ZEN vibes:
Sway and swoon with the trees (and your lover) at the Lincoln Park Caldwell Lily Pool. With ever-flowing streams as your soundtrack, you can recover your zen and your spark amidst the lush landscapes of Alfred Caldwell’s signature style. Walk four blocks east to the lake front trail.
RELIC vibes:
Take in the history of Chicago’s comedic past and relish in its present endevours at Old Town’s Second City Theatre. This storied spot is home to alums like Tina Fey and still celebrates Chicago-style sketch and improv comedy. Head to Main Stage where you can order food and drinks while you watch the show. Heads up: Don’t be the dude who suggests obscenities when prompted for suggestions. You will get called out for that shit. This is Chicago.
After the show, head to Old Town Ale House across the street and sip a cold one between the same walls that once circled Al Capone. If there was ever a five-star dive bar, this is it. Oh, and if you ever wanted to pound your beer-clenched fist as you throw your head back and hurtle with laughter, do it here. Just clean up after yourselves. And bring cash.
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