Planning a first date comes with lots of pressure. You want to pick a place that’s the right mix of romantic, impressive, casual, and cool, with food and drinks you'll both be able to enjoy, while enjoying each other’s company even more. There’s no lack of options in Chicago, but when it comes time to decide where to bring your newest love interest, it can almost be too overwhelming. Ahead, we've found six bars and restaurants around the city that will make the perfect setting for your budding love story.
You could head to a nice restaurant for a meal—or, if you want to liven the night up a little bit, you can visit quite possibly the hippest piano bar in Chicago. Tack Room is the perfect combination of a cool and cozy cocktail bar with killer live entertainment to boot—who wouldn’t bond over belting out some of your favorite piano-man tunes? Even better: It’s part of Pilsen’s Thalia Hall building, so you can make a night out of popping in and out of the other establishments. Hear more music at Thalia Hall, nosh on some snacks at Punch House, or grab a full meal at Dusek’s. 1807 S. Allport St., 312-526-3851
You’re sure to impress by taking a date to The Violet Hour, a pre-Prohibition-style cocktail bar in Wicker Park. The feeling of exclusivity starts outside, with the singular light bulb noting its entrance—the facade features an ever-changing mural. This ambiance continues inside with majestic, high-backed leather chairs, crystal chandeliers, and an elegant bar and tables. Plus, there's no cell phone use allowed in the lounge, so you can be sure to focus on each other, rather than incoming texts or your Instagram feed. 1520 N. Damen, 773-252-1500
Even when the connection is there, sometimes it's tough to kick off the first-date chatter without asking cliché small-talk questions—which is why going somewhere that’s conversation-worthy in itself can be key. The Bedford is not only located in a 1920s historic landmark building, but the space itself is a converted bank vault with many of its original elements still intact. Pretty much everywhere you and your date look, you’ll have something to discuss and jointly ooh-and-ahh over. 1612 W. Division St., 773-235-8800
Sparrow is comparable to that neighborhood bar you thought only existed in movies. Situated in an art-deco apartment building, Sparrow was recently restored after 75 years and modeled after old-school Chicago hotel lobby bars. The vibe is elegant and inviting; perfect for an intimate conversation over a couple of 1930s-era cocktails. 12 W. Elm St., 312-725-0732
We’re not sure if it gets more romantic than RM Champagne Salon’s outdoor patio. The lights, brick interior, and eclectic tables seem as though they were set up specifically for first dates. Head there for a full dinner date, or stop in for some drinks (they have more than champagne—though we’re all for bubbly on a first date) and late-night snacks under the glow of the string lights. 116 N. Green St., 312-243-1199
The rooftop restaurant and open-air terrace atop the Chicago Athletic Association Hotel is the perfect setting for a casual, fun, before-dark meet-up. Head there for a brunch, lunch, or a happy-hour date, and take in the stunning vaulted glass and steel atrium and the views of Millennium Park while you get to know each other. Don't want your date to end? Head downstairs to the Game Room for some billiards, bocce, or checkers. 12 S. Michigan Ave., 312-792-3502
Photography courtesy of Tack Room; by Joni Kat Anderson (Violet Hour); courtesy of Cantina 1910; courtesy of The Bedford; by Nick Fochtman (Sparrow); by Anthony Tahlier (RM Champagne Salon); courtesy of Chicago Athletic Assocation Hotel