Romantic Spots in Chicago
The sexiest scene featuring a Chicago landmark happened in the 1980s flick “Risky Business” when Tom Cruise’s character took Rebecca De Mornay on a wild ride on a CTA train. It’s memorable, thrilling, and tempting, but in today’s volatile climate, we would highly discourage recreating it.
However, for those romantic at heart, we’ve gathered a great list of local landmarks and other points of interest perfect for sharing a romantic kiss. Some are obvious choices, while others are hidden gems destined to become favorites.
Get Cozy in a Red Leather Booth at Bavette’s
Mysterious, sexy, and dark, the French-themed lounge and steakhouse offers two levels where guests may dine, drink, and enjoy each other’s company. Reserve one of Bavette’s red leather booths for a romantic atmosphere. It’s roomy, comfortable, and slightly isolated from the bustling dining room—perfect for sharing generous portions of the bone-in, dry-aged ribeye, shellfish towers of oysters, jumbo shrimp, and lobster; and short rib Stroganoff with hand-cut fettuccine and cremini mushrooms.
Steal a Smooch Under the Bean
Referred to by locals as “The Bean,” Cloud Gate is a public sculpture designed by British artist Anish Kapoor. It’s one of the centerpieces of Millennium Park and weighs in at more than 110 tons. The mirrored surface offers an amazing reflection of the city skyline, which is breathtaking on a bright, clear day. Visitors can walk underneath Cloud Gate, which is surprisingly concave, making it an excellent backdrop for romantic photos.
Snuggle up During a Horse-Drawn Carriage Ride
Taking a nostalgic horse-drawn carriage ride is one of the best ways to explore the city. Noble Horse is one of Chicago’s prominent companies offering tours of the Magnificent Mile shopping district. The carriage will pick you up from a nearby hotel or restaurant for an ultimate romantic surprise.
Gaze Upon the Skyline at Everest
Situated on the 40th floor of the Chicago Stock Exchange, Everest specializes in exquisite Alsatian cuisine. The award-winning restaurant, led by renowned chef Jean Joho, takes diners on a sensory journey with menus featuring smoked meats, cold-pressed lobster, and regional wines, all complemented by breathtaking views of the skyline.
Embrace Under the Michigan Avenue Bridge
Chicago’s top boat tours operate year-round, many making their way to the Chicago River. As boats pass under the gloriously lit Michigan Avenue Bridge at night, it’s an ideal moment to sneak in a romantic kiss—creating lasting memories in a picturesque setting.
Feel Glamorous in the Pump Room’s Booth One
The legendary Pump Room, located inside Public Hotel Chicago, has been a celebrity hotspot for nearly 80 years. To have an over-the-top evening, request Booth One—where A-Listers have dined. It features a vintage rotary-dial telephone, adding an element of nostalgia. The menu presents classic American dishes re-imagined by Michelin-starred chefs, providing a luxurious dining experience.
Delight in the Signature Room at the 95th
The Signature Room at the 95th, located above 360 Chicago (formerly John Hancock Observatory), offers spectacular views of the Magnificent Mile. Known as a romantic destination, it has seen hundreds of marriage proposals. Request Table 111 for the best vistas, and the kitchen can add personal touches, like handmade truffles or custom messages on desserts, enhancing the romantic atmosphere.
To truly set the mood, a harpist is available on most nights, contributing to the enchanting dining experience.