3 Great Chicago Date Ideas

Young Couple visiting Christmas Market in Milan

Looking for romantic things to do in Chicago? Here are three red-hot itineraries to keep you and your main squeeze toasty on even the coldest Chicago nights. Date night in Chicago — solved!

DATE NIGHT OPTION 1: Bubbly Comedy

Nuzzle up in the dazzling dining room or romantic patio at Old Town’s Perennial Virant, where the food is farm-to-table fresh and the drinks are deliciously inventive. Share pillowy potato gnocchi with roasted cauliflower and crispy pork, and a Midwestern Cheeses board with seasonal preserves, candied walnuts and a honeycomb, while sipping a glass of sparkling rosé or a Brown Butter Old Fashioned.

Head to The Second City for the “Best Of” show, featuring some of the top sketches, songs and improv from their 52-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.

End the night basking in chic Gold Coast luxury in a Celebrity Suite at the Ian Schrager-designed PUBLIC Chicago Hotel. 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 OPTION 2: Sweets, Sips & Sprited Competition

Let your palates run wild with bold, modern Mexican cuisine from Dos Urban Cantina. Feast on goat albondigas with black mole, kick the night off with a couple of margaritas or palomas (tequila, Aperol and grapefruit), and end on a sweet note by sharing what has been called the “Best Piece of Chocolate Cake”.

Visit Logan Square’s Chicago Distilling Company and see what the DiPrizio family has been up to. Book a tour and learn how the third-generation distillers turn locally farmed grain into vodka, whiskey and award-winning gin. Get in on the beercade trend at Emporium Arcade Bar and challenge your date to a competition among 24 arcade games, 13 pinball machines, six pool tables and more.

DATE NIGHT OPTION 3: Romance with a View

Embark on a guided horse and carriage ride through Chicago’s Gold Coast, one of the country’s most affluent neighborhoods. Watch historic mansions go by as you snuggle under a blanket.

 

Hold hands on the 94th floor of the John Hancock Center. The TILT at 360 CHICAGO observation deck serves up breathtaking views of Chicago’s lakefront and skyline from 1,000 feet above Michigan Avenue Visit the Streeterville neighborhood for seasonal eats at GreenRiver Chicago. Settle in and order the chef’s tasting menu, an eight-course meal comprised of modern Midwestern fare, and sip from the Chicago On Tap beer menu.
Find ultimate luxury and privacy 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. For an extra $15 per person, you can keep the romance going with breakfast in bed the next morning.

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