Date Ideas
in Chicago, IL
Showing 1 - 10 out of 10
We’ve found the best spots near you to give you the variety you have been craving for. Think outside the box and dare to try something different for your next date night! Turn a regular night into one to remember forever.
70 W Madison St
Chicago, IL 60602 Directions
Get ready to chow down on some of the best food in the city on the Chicago Dine-Around tour. It guarantees the best restaurant-hopping you'll ever do; stopping at the first restaurant for hors d'oeuvres, the second for the main course and the third for desert. Bring your appetite and bon appetit!
806 N Michigan Ave
Chicago, IL 60611 Directions
Ride around Chicago like old-time royalty in a horse-drawn carriage. Chicago Horse & Carriage Ltd offers romantic rides through the city's neighborhoods like Gold Coast, Lake, Michigan Avenue, Navy Pier, and Millennium Park.. Gentlemen, call ahead to reserve extras like roses by the dozen and a lap blanket.
425 S Financial Pl
Chicago, IL 60605 Directions
Paris is considered to be the most romantic city in the world. Since the City of Lights is an ocean away, dining on French cuisine at the Everest restaurant is second best to dining at the Eiffel Tower. The restaurant is located on the 40th floor of the Chicago Stock Exchange.
306 S Halsted St
Chicago, IL 60661 Directions
Spend some time hanging out in Chicago's Greektown. The neighborhood is home to nightlife spots, restaurants, gift shops and galleries that celebrate the culture of Greece. Nine Muses Bar & Grill, Spectrum Bar & Grill, Dugan's on Halsted, and Pegasus Restaurant & Taverna are just a few places to wine and dine in Greektown.
1960 N Western Ave
Chicago, IL 60647 Directions
Finish off the night with hot fudge sundaes at Margie’s Candies and start your love story with everything sweet and decadent or request the booth where the Fab Four had sat.
601 N State St
Chicago, IL 60654 Directions
Pop champagne on a romantic date at Pop's for Champagne, a premier champagne bar that serves up over 100 kinds of champagne and other drink at the full-service bar. Though champagne is tasty, we don't advise drinking on an empty stomach. Be sure to try something from the menu.
201 N State St
Chicago, IL 60601 Directions
Shout your love from the roof tops! Or just go on a romantic date out on the town at ROOF on theWit, the lounge at the Wit Hotel. Wine and dine while overlooking Chicago from the outdoor patio or the hangover space. The dinner menu offers a variety of entrees from steak to pizza and the drink list certainly doesn't disappoint.
875 N Michigan Ave
Chicago, IL 60611 Directions
Whether you are a tourist or a local you will enjoy fine dining at the Signature Room at the 95th. Providing a romantic intimate atmosphere and the best view for lunch, dinner, or brunch.
600 E Grand Ave
Chicago, IL 60611 Directions
Fall in love on Lake Michigan aboard the Tall Ship Windy. The topsail schooner sets sail from Navy Pier and the trip offers beautiful views of the city. Private charters are available if you want your romantic date to be even more special.
42 East Ontario Street
Chicago, IL 60611 Directions
The Escape Game Chicago is located at the center of Chicago’s fun and excitement in River North. You can find us less than two blocks west of The Magnificent Mile, surrounded by many great restaurants and hotels.
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