A Sunday stroll through a neighborhood farmer's market or Friday night sojourn to a street fest with food trucks aplenty is a great way to introduce your date to new cuisines while still being able to walk, talk and enjoy the summer scenery.
If you do decide to go to a restaurant, make it an early dinner (I suggest Balena, Bluebird or Tango Sur) and then check out a new play at the Steppenwolf Garage or comedy show at iO Theater, both tickets $20 or less. Have a drink afterwards (I'm partial to The Violet Hour and Bangers & Lace) to discuss your favorite parts.
For the artists:
Bottle & Bodega and Arts n Spirits are perfect spots for couples to sip on wine or mimosas as they paint. And while a thorough canvassing of the Museum of Contemporary Art and a Ferris Bueller-style jaunt through the Art Institute are essential outings for any artsy duo, Chicago has a multitude of other musuems to explore. Check out a gallery opening in Pilsen or the South Loop, walk through the highly underrated Museum of Contemporary Photography or make pottery à la Ghost at Penguin Foot.
For the nerds:
If you're into vintage games, make a date at one of the city's best arcade bars: Emporium, Headquarters or Logan Hardware (where you can also browse for vinyl, candy and comic books). Then keep the nerdy fun going all night long with sci-fi movie trivia at Logan Theatre or a hilarious Stars Wars cabaret at Gorilla Tango.
For the music lovers:
Bring a blanket and a bottle of wine to Downtown Sound for free music in Millenium Park, or pay $10 each to see the Chicago Symphony Orchestra on the lawn at Ravinia. Other cosy and cost-friendly spots to hear live music around the city include jazz at The Green Mill, folksy sets at Evanston Space, Free Music Mondays at The Empty Bottle and Acoustic Brunch at Schubas.
For the athletes:
Go for a scenic bike ride on the lakefront or through the majestic Cook Country Forest Preserve, and find places to stop for burgers and beers along the way. Feel like challenging each other to a game of one-on-one? Break out the tennis racquets at one of these Chicago courts or race up the climbing wall at The Ledge in Old Town.
For the adventurers:
Chicago was recently named the city with the most adrenaline junkies in America, perhaps because of the endless thrill-seeking possibilities that await around every turn. For a truly exhilirating date to remember, take a trapeze class at the Actor's Gymnasium in Evanston, ride in a hot air balloon over Illinois or tandem sky dive at the Chicagoland Skydiving Center in Rochelle.
For the bookworms:
Experience the world-renowned Uptown Poetry Slam at the Green Mill, or visit one of the many storytelling nights at bookstores all over town. If you both have an undying love for the Bard, check out a performance by The Shakespeare Project at a library near you.
For the romantics:
Take a picnic dinner to the beautiful Promontory Point at sunset, snuggle up on the roof of The Wit for Movie Mondays or spring for $14 cocktails at the Signature Room to gaze down at Chicago from the 95th Floor (believe me, it's worth it). If you really want to impress that special someone, a spectacular view can't be beat.
What are your favorite date spots in Chicago?