Date Night can mean a lot of things to different people. From the usual eating out, be it at a fancy restaurant or your favorite neighborhood joint, to trying new experiences or even staying in, date night is a good way to bond with your partner, and keep the romance alive. Here are a few suggestions to keep your date night fresh and interesting in Chicago.

Mindy’s Hot Chocolate

1747 N Damen Ave

First opened in 2005, Chef Mindy Segal’s Hot Chocolate Restaurant has quickly become one of Chicago’s go-to spots for comfort food. Once you walk past the decadent display of pastries, you’ll find an industrial chic interior fitted in wood and chocolate browns, featuring a large bar and open kitchen. The restaurant is famous for their (what else) hot chocolate, which is decadent yet comforting at the same time. Besides delicious hot chocolate, Mindy’s also serves up lunch, dinner, and weekend brunch.

Brunch, lunch, and dinner offerings constantly change based on seasonal availability of ingredients. Before summer is over, try the Soup of the Day with the Smoked Whitefish Tartine for dinner.

Le Bouchon

1958 N Damen Ave

Le Bouchon, which opened in 1993, brought the French bistro style of cooking to Chicago. The restaurant serves French classics like French onion soup, escargot, frog legs, steak frites, and bouillabaisse, all of which pair well with a selection of fancy French wines. Despite being housed in a nondescript brasserie, the restaurant has been named one of America’s Best French Restaurants by Time Out magazine, and counts former US President Obama a fan.


3201 W Armitage Ave

Scofflaw puts its hat in the ring at the go-to Logan Square cocktail destination by serving up something distinctly different. Opening just a year ago, Danny Shapiro’s lavish Victorian-meets-Wild-West surroundings have quickly become a local favorite for their signature gin cocktails, which Shapiro himself concocted.

Notably, drinks aren't as expensive as the place looks. Fan favorites include the Forest Floor, which smells faintly of fir trees, and the seasonal drinks such as the Basil Bramble. The bar also serves food, a creative take on classic bar favorites. Try Chef Mike Neeley’s guapachosa, a sandwich laden with brisket, pork loin and avocado.

The Chopping Block

4747 N Lincoln Ave

Taking cooking classes together can also be a great bonding activity, and cheaper in the long run than always eating out on date night! The Chopping Block, a local gourmet retail store, has been offering culinary classes for 20 years now, teaching many Chicagoans how to cook. Their lessons are fun and interactive, and its Culinary Boot Camp has been named “Best Cooking Class” by Chicago Magazine.

Mercury Cruises

112 E Upper Wacker Dr

There’s nothing more romantic than sharing a bottle of wine under the stars, and Mercury Cruises' new offering is the Chicago by Night date night and wine special, which is pretty much exactly what it sounds like.

Happening Thursdays & Fridays til October 6, the cruise will take you to see the skyline on the Chicago River and Lake Michigan, and comes with a complimentary bottle of wine. The cruise leaves at 8:15pm from Chicago’s Riverwalk at Michigan Avenue and its dock at Wacker Drive (112 E Wacker Dr).


What are some of your favorite Chicago date night traditions? Find more itinerary options here or tweet at @ChooseChicago with your best ideas, and we’ll share them with our followers!