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 dazzling dining room or on the romantic patio at Old Town’s The Kennison, where the food is farm-to-table fresh and the drinks are deliciously inventive.
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 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 800-1,200-square-foot 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
There’s no better date night than a lovebird-led spot like Dos Urban Cantina, run by a husband and wife duo. Kick the night off with a couple of margaritas or palomas (tequila, Aperol and grapefruit), enjoy contemporary Mexican fare that are almost too pretty to eat, and end on a sweet note by sharing what’s been called the “best piece of chocolate cake” in Chicago.
Next, 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. Just next door, you’ll find Emporium Arcade Bar, 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
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-poundings views of the skyline. Then head across the street for dinner at Spiaggia, for the upscale Italian that’s a favorite date night spot of local celebrities, including Barack and Michelle Obama.
Book an intimate apartment-style suite at Ivy Boutique Hotel, a 16-story gem just off The Magnificent Mile. The 63 guest rooms come with cozy Michigan goose down pillows and Frette bathrobes. You can keep the romance going with breakfast in bed the next morning.