Romantic Things to Do in Chicago

Chicago is a city with style and verve, and its beautiful parks, picturesque waterways, and vertiginous heights all make the perfect backdrop to a romantic excursion. From 2-passenger helicopter flights to Lake Michigan cruises and after-dark speakeasy visits, here’s how to enjoy a special trip to Chicago with your significant other.

Cruise Lake Michigan at Sunset

Lake Michigan is almost oceanic in scope, and a night out on the water is a classic Chicago experience. Book an early evening tour to watch the sun descend over the iconic Chicago skyline, and enjoy a romantic moment out on the deck. Alternatively, a dinner cruise—complete with gourmet dishes and flutes of sparkling wine—is the perfect way to toast a special occasion.

Enjoy a Couple’s Photo Shoot in Millennium Park

Visit one of the Windy City’s most in-demand sightseeing destinations—and enjoy a special way to record your memories for posterity—when you book a couple’s photo shoot. Explore the greenery and public artworks of Millennium Park, admire the perspective on the Loop’s gleaming skyscrapers, and see the famous Cloud Gate sculpture by Anish Kapoor—better known as “The Bean.” Your very own photographer will be present to show you the sights and capture your romantic moments.

Sip Cocktails in the City’s Speakeasies

During its Prohibition-era heyday, Chicago was filled with speakeasies (not to mention infamous gangsters the likes of Al Capone). Today, that legacy lives on in the city’s plethora of top-notch cocktail haunts (which, today, are thankfully free of bathtub gin). Book a speakeasy tour for a dose of history and to discover a number of cozy, candlelit drinking dens with your significant other.

Book a Private Helicopter Tour

Few views of Chicago can compare with the ones afforded by a helicopter—and taking to the air on a freewheeling journey above the skyscrapers is one of the city’s most popular romantic experiences. Book a private flight for a particularly intimate experience, and enjoy an indulgent accompaniment in the form of Champagne and chocolates.