While whisking your lover off to a 10-course meal at one of the city’s finest restaurants makes for a lovely evening, sometimes it’s just as fun to plan something a bit more low-key. From an underground tiki bar to a riverside retreat, we found some cool, casual, and very Chicago eateries for your next date night.
RM Champagne Salon
Love is in the air on RM Champagne’s open-air patio.
Keep things demure at this kitschy-yet-glamorous hideaway just off the beaten path along Restaurant Row. The fireplace situated on one side of the elegant dining room is as beautiful as it is seductive; pull up a couple seats beside it and make sure to cover your bases with the ultimate date night trifecta: Champagne, fresh oysters, and something sweet. 116 N. Green St., 312-243-1199
Rockit Burger Bar
Bring your honey, your appetite, and your Iron Chef-like creativity to Rockit’s weekly BurgerLab, every Saturday from 7 p.m.-close, for a gut-busting date night. The DIY lab lets you choose from a plethora of buns, specialty meats, sauces, cheeses, and other unexpected toppings to create the most outrageously delicious burgers you lovebirds can come up with. 3700 N. Clark St., 773-645-4400
Romance meets classic literature inside Hubbard Inn's library lounges.
River North's coziest establishment has plenty of quiet nooks and crannies within its eclectic library lounges to curl up with a cocktail and a good conversation, and the comprehensive drink list is the perfect excuse to use your knowledge of beer, wine, or mixology to impress your date. If the evening is going well, may we suggest a round of Lagunitas A Little Sumpin' Sumpin' Ale and some plates meant for sharing: bacon-wrapped dates, lamb meatballs, and seared scallops?
If the dining experience at Tony Mantuano’s new American tavern wasn’t designed with date night in mind, then they sure could’ve fooled us. River Roast’s utterly romantic riverside locale lends a picturesque backdrop for sipping inventive cocktails and sharing a feast fit for a king and queen. Try the supremely juicy wood-smoked chicken, served whole and carved tableside, washed down with the potent Acceptable Addictions. 315 N. LaSalle St., 312-822-0100
Enjoy an ice cream ménage a trois at Jeni’s.
Make dessert the main event with fancy scoops at Jeni’s Southport. The Ohio-based ice cream shop rotates its menu frequently, showcasing a variety of seasonal ingredients and flavors like sweet corn and blackberry, Queen City cayenne, and a new Intelligensia Black Cat Espresso number that packs a serious hit of caffeine. The best way to stay cool on your hot date? Order a dish with a few different flavors and two spoons. 3403 N. Southport Ave., 773-348-7139
Three Dots and a Dash
Enjoy a Lady and the Tramp moment—tiki style—with the made-for-two Pieces of Eight cocktail at Lettuce Entertain You’s subterranean bar. The sweet concoction blends light Caribbean rum with passion fruit, lemon, and falernum, and comes in a seashell-shaped glass. Soak up that rum with island-inspired fare like coconut shrimp and Polynesian spare ribs coated in a pineapple glaze. Finding seats can be difficult so be sure to make a reservation for a private table for you and your main squeeze. 435 N. Clark St., 312-610-4220