Date Ideas
in Chicago, IL (showing 1 - 10 out of 10)

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!

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.

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.

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.

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.

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.

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.

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.

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.

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.