Whether it’s a first date or a 10th anniversary celebration, a night on the town never hurts. Consider these eight Chicago date spots where handcrafted cocktails, favorite films and beautiful views await—your perfect date starts here.
Explore Chicago by water on Chicago's First Lady.
Chicago's First Lady Architecture Tour
What better way to experience the city than by boat? Let Chicago’s First Lady take you and your date on an exploration of the city’s iconic architecture, from the Civic Opera House to Marina City, with detailed information on legendary designers and different architectural styles presented along the way. Relax a little on the 90-minute tour and enjoy a full-service bar and snack bar varying by cruise—then stop by Chicago Architecture Center to round out the experience. 112 E. Wacker Drive, 312.922.3432, architecture.org
There’s little point in arguing Geja’s status as Chicago’s most romantic restaurant. Prepare to be enchanted with the Arabian Nights cocktail featuring Empress 1908 gin, lemon juice, simple syrup and hints of jasmine to The Connoisseur fondue of beef tenderloin, white shrimp and Australian lobster tail. Serenades from classical and flamenco guitarists add even more romance to the evening affair. 340 W. Armitage Ave., 773.281.9101, gejascafe.com
Can a date get any more nostalgic than a night at the drive-in? From the buttered popcorn, hot dogs and cheese fries to the big screen and breeze, this Pilsen neighborhood destination has it all. Expect classic flicks like Ferris Bueller’s Day Off, Grease and The Sandlot, plus blockbusters like Jurassic Park, Harry Potter and The Lion King. 2343 S. Throop St., chitownmovies.com
The Comedy Bar
Need an icebreaker? This might be just the spot for you—located in the city’s iconic Mag Mile, The Comedy Bar has been touted as one of the best comedy clubs in Chicago, offering both a main performance stage and rooftop patio. Don’t miss out on the full bar and dinner menu from Gino’s East featuring favorites like the Meaty Legend deep dish with pepperoni, Italian sausage, bacon and Canadian bacon, charred brussel sprouts with pancetta, garlic and panko and the deep dish brownie baked until gooey and topped with vanilla ice cream. 162 E. Superior St., 312.623.3532, comedybar.com
Lots of laughs are in store at The Comedy Bar.
Few things are better than a drink with a view, and BAR 94 is taking happy hour and your date to a whole new level—the 94th floor of the John Hancock Center, to be exact. Patrons should be prepared for an elevated experience of cocktails made from locally sourced KOVAL Distillery spirits and handcrafted Revolution Brewing beers, all accompanied by one of the best bar views in Chicago. The bar’s location 1,000 feet over the city’s iconic Magnificent Mile in the observation deck of Chicago 360 is shared with TILT, the city’s highest thrill ride. 875 N. Michigan Ave., 888.875.8439, 360chicago.com
Château Carbide at the Pendry Chicago
There's something special about this seasonal outpost—whether it’s the Cote d’Azur-inspired decor or its perch on Pendry Chicago’s rooftop, Château Carbide is a date night must. The allure of the French countryside and an unmistakable Chicago twist come together in a sun-soaked garden setting with Château D’esclans Garrus rosé; the Clever Girl cocktail featuring champagne liqueur, lemon and sparkling wine; a picnic for two; and creative sushi with ingredients like clementine and truffles. All of these delectables can be enjoyed while taking in the stellar city views . 230 N. Michigan Ave., 312.777.9000, pendry.com
City Mini Golf
If you’re looking to score a hole-in-one, City Mini Golf awaits with a classic Chicago-themed course and views of one of the most iconic skylines in the world. Plus, its proximity to Butler Field, Navy Pier and Millenium Park make for a whole day of fun with the Ferris wheel, seasonal festivals and fireworks. After you work up an appetite, stop by a nearby Loop favorite like Giordano’s Pizza for some of the city’s best deep dish, Eggy’s Diner for urban comfort food or Billy Goat Tavern for a burger with a side of Cubs history. 337 E. Randolph St., 773.809.5589, cityminigolf.com
If laid-back is your style, this old-school-vibe Loop bar is the perfect place for a no-fuss date night. Self-proclaimed as having “fancy enough cocktails and fine spirits,” the Lone Wolf Tavern serves up craft beer like Three Floyds on tap; classic cocktails including Manhattans, Old-Fashioneds and French 75s; and—new to the Lone Wolf—craveable eats from Chicago legend Tamale Guy. 806 W. Randolph St., 312.600.9391, lonewolftavern.com
The dining room at Lone Wolf is a cozy date night setting.
Photography by: By Barry Butler Photography; Courtesy of The Comedy Bar; By Wade McElroy