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The 13 Best First Date Spots In Chicago

By Lauren Whalen in Arts & Entertainment on Nov 18, 2015 7:00PM

These days, we look for love online and increasingly, by swiping right or left on our smartphones. But what to do when the time comes to meet face to face? Chicago is bursting at the seams with interesting (and often delicious) date spots, but the choices can be overwhelming—especially if your priority is finding somewhere fun, affordable or convenient in case you find yourself needing make a quick escape. Below are 13 ideas for everyone from whisky snobs to culture vultures to stone-cold weirdos. Raise a glass to love, or just a really excellent night—and remember, these are our favorite spots, but they don't have to be yours. Please let us know where you like to take your first dates around Chicago.

A cocktail at Scofflaw.

Scofflaw (3201 W. Armitage Ave.)
For an intimate yet fun atmosphere that's first-date friendly, Scofflaw can't be beat. The Logan Square hotspot not only offers a varied menu of craft beers and gin-focused cocktails to calm your nerves, but also stays open until 2 a.m. (3 a.m. on Saturday) for dates going especially swimmingly. The kitchen offers affordable foodie-friendly grub including edamame hummus and a pork loin schnitzel sandwich, and a variety of nibbles to share. Go on a weeknight to maximize conversation, or a weekend to get a little more rowdy.

Photo from last year's event at Dvorak Park, photo by joe mazza brave lux inc

Too Much Light Makes the Baby Go Blind (The Neo-Futurists, 5153 N. Ashland Ave.)
It's virtually impossible to have a bad time at this little show turned Chicago institution. Serial daters can even go more than once: the Neo-Futurists' thrice-weekly attempt to perform 30 plays in 60 minutes guarantees a completely original show every time. Now in its twenty-fifth year, T.M.L. (as it's known to fans) is quick, dirty and according to its website, "performed from a perspective of absolute honesty." Even if there are no sparks between you and your date, a fantastic experience will be had by all. Hungry beforehand? Visit nearby Kopi Cafe (5317 N. Clark St.) for sandwiches, soup and fantastic wine and coffee in a beautiful bohemian setting.

The Art Institute of Chicago (111 S. Michigan Ave.)
Before you protest "but I've been there a million times with my mom!" consider this: The museum voted number one in the world by TripAdvisor once hosted a first date for the ages. A couple now known as Barack and Michelle Obama visited the Art Institute on their inaugural outing. Saving your pennies for the second date? Go on Thursday night between 5 and 8 p.m., when the museum is free to Chicago residents. If you want to fully recreate the First Couple's date, take a lakefront walk and discuss your favorite paintings. Sure, it's getting cold, but that's all the more excuse to snuggle up afterward.


Bang Bang Pie Shop (2051 N. California Ave.)
Located just three blocks south of the Blue Line, Bang Bang specializes in custom roasted coffee blends, excellent counter service and more than enough carbs to satisfy you and your date. Enjoy a small but hearty menu of sweet and savory pies and biscuits (with vegetarian options aplenty), and get to know your crush as the smell of baked goodies fills the air. Because really, what's the worst that can happen when you're surrounded by pie?

Zaleski & Horvath (1323 E. 57th St.)
We are all about the sandwiches, coffee and fresh-baked pastries at Zaleski & Horvath, a bustling cafe and deli in Hyde Park with longstanding community ties. You can order and pay for your food at the counter, then nab a table among studious University of Chicago students. When the weather's nice, the Hyde Park location also has pleasant outdoor seating. Their signature Sammies include The Godfather—that's made with smoked prosciutto, fresh mozzarella, and balsamic vinegar on French bread, and The Mae Wilson, which includes roasted turkey, cheddar, guac, and chipotle mayo on whole wheat.

via Tapas Valencia

Tapas Valencia (1530 S. State St.)
When it comes to first-date food, there's none more fun than tapas. This South Loop locale may look unassuming on the outside, but inside the decor is colorful, the atmosphere friendly and the options affordable and abundant. Mix the cold with the hot with the spicy, and see if your preferences complement your date's. If all's going well, split a dessert of profiteroles with ice cream or the featured Flan of the Day.

La Creperie (2845 N. Clark St.)
It's been through a lot (including temporary closing) since its 1972 opening, but this French bistro on the border of Lakeview and Lincoln Park has never lost its cozy yet utterly romantic charm. Choose from a menu of equally delectable sweet and savory crepes, and a host of beers and wines, enjoy the low lighting and old school decor, or eat on the patio if the weather is mild. You and your paramour can make things quick or take it slow and easy like the Europeans do at mealtime. If you share a love of art films, take in a flick before or after dinner at Landmark Century Centre Cinema, just across the street at 2828 N. Clark St.

via Fountainhead

Fountainhead (1970 W. Montrose Ave.)
As a friend and former first-dater said, "If nothing else, I always got a good beer." Don't be put off by the possible Ayn Rand reference in the name, or you'll miss out on the ideal first date spot. Casual yet classy, this Ravenswood gastropub boasts specialty beers, bourbons and whiskeys, seasonal bar and dinner menus with plates to share, and proximity to the Brown Line if you need a quick escape. Fountainhead's scenic rooftop garden is closed for the season, but if the two of you connect, you can always visit again for your six-month anniversary.

Guthrie's Tavern (1300 W. Addison St.)
Their website proudly states "WE HAVE BEER," but even better for breaking the ice, Guthrie's has board games. Enjoy a round of Scrabble, Yahtzee or Balderdash with your round of drinks, and bask in the friendly and flattering low lighting. Impress your plus-one (or win Trivial Pursuit) with the history of this Wrigleyville watering hole: once a grocery store dating back to 1900, it was turned into a corner tap after Prohibition ended in 1933, and has been operated by the same owner for over 30 years. More into icebreakers of the arcade variety? Try Logan Arcade (1420 W. Fullerton Ave.) or Headquarters Beercade (2833 N. Sheffield Ave. in Lakeview and 213 W. Institute Pl. in River North).

Rootstock Wine & Beer Bar (954 N. California Ave.)
This modest Humboldt Park restaurant is described as a "labor of love" for its owners, three former employees of Webster Wine Bar. Said love is expressed in every detail, from the carefully crafted selection of wine and beer, to the sweetly curated menu of charcuterie, cheese and entrees with locally sourced ingredients. There are no reservations, no dress code and accessible street parking, and the two of you are free to keep eating and drinking until 2 a.m. (the kitchen's open until 1). If you're feeling the love but desire a change of scenery, head to the California Clipper (1002 N. California Ave.) for artisan cocktails in a speakeasy setting.

Skylark (2149 S. Halsted St.)
This dark, divey spot made our list of best places to break up with someone, but don't let that dissuade you. Woo your date over Skylark's delicious tater tots and dipping sauces after choosing from their rotating beer selection. We're partial to biking to this out-of-the-way bar, then taking our bikes around the corner to Ping Tom Memorial Park and sitting by the river.

The Wormhole Coffee (1462 N. Milwaukee Ave.)
Many first daters prefer coffee shops: no liquid libations to loosen the tongue and inhibitions, and an easy "gulp and go" if conversation is especially stilted. With its plethora of '80s movie posters, toys and memorabilia on display, the Wormhole provides plenty of fodder for nostalgic chatter. If your date isn't a Star Wars fan, you can always participate in the prime people-watching the cafe offers. Those wired to the hilt on coffee, conversation and chemistry can easily grab dinner or drinks in bustling Wicker Park. If you two share a love of literature, stop by Myopic Books (1564 N. Milwaukee) and see who can find a vintage copy of In Cold Blood first.

The International Museum of Surgical Science, by Marielle Shaw

International Museum of Surgical Science (1524 N. Lake Shore Dr.)
One of the best parts of dating is finding someone who shares your passions, no matter how strange or offbeat. Tired of the bar scene? Meet your potential match at this historic lakefront mansion that houses 18th century surgeons' kits, detailed anatomical illustrations and a special exhibit on laboratory diagnostics as detective work. Pick your favorites from the Museum's collections of 7,000 medical artifacts that span centuries of medical history, from X-ray therapy to acupuncture, and marvel together over the original plaster cast of Napoleon's death mask. If you and your date can't stop gabbing and geeking out, you'll know it's forever.