Chicago has something for every kind of date, from cozy bars perfect for a first date to romantic restaurants worthy of milestone anniversaries. Whether it’s with a new flame or a long-time love, your Chicago date night will be one to remember.
Date night 1: Bubbly and comedy
Grab a seat in the cozy dining room or on lush patio at Old Town’s Orso’s Restaurant, a family-owned Italian spot filled with old-world charm.
Next, head to The Second City for one of their classic improv shows, featuring some of the top sketches, songs and improv from their more than 50-year history. The company that brought the world Tina Fey, Stephen Colbert, and Steve Carell will have you chuckling all the way to post-show drinks.
Have a champagne toast at the ultra-romantic, all-season rooftop The J. Parker, with 360-degree views of Lincoln Park and Lake Michigan as the perfect backdrop.
End the night basking in chic Gold Coast luxury in a Celebrity Suite at the Ambassador Chicago. These spacious rooms feature king-size beds with imported linens, separate living spaces, and bathrooms with tubs, so you can soak up the romance in style.
Date night 2: Sweets, sips & spirited competition
Visit Logan Square’s Chicago Distilling Company for a tour to learn how the third-generation distillers turn locally farmed grain into vodka, whiskey, and award-winning gin. You’ll find Emporium Arcade Bar just next door, where you can challenge your date to a match on one of the 24 arcade games, 13 pinball machines, or six pool tables.
Your resting place for the night? Bar-restaurant-inn Longman & Eagle. The six-room hideaway sits above the first-floor, whiskey-focused tavern and features eclectic furnishings and commissioned art.
Date night 3: Romance with a view
Book an intimate apartment-style suite at Ivy Hotel, a boutique gem just off The Magnificent Mile. The 63 guest rooms come with cozy Michigan goose-down pillows and Frette bathrobes. You can get the romance going with breakfast in bed.
Embark on a romantic stroll or bike ride through Chicago’s Gold Coast, one of the country’s most affluent neighborhoods. Admire historic mansions and maybe pop into one of the areas swanky boutiques.
Next, jet up to the 94th floor of 875 N. Michigan Ave. (formerly the John Hancock Center). Dare to step onto TILT at 360 CHICAGO, the observation deck’s 1,000-foot thrill ride that offers heart-pounding views of the skyline. Afterward, have dinner on a rooftop at NoMi Kitchen or Shanghai Terrace. Watching the city skyline light up around you is the perfect way to end a romantic date night.
