Photo from The St. Regis Chicago

Date nights are easy at The St. Regis Chicago. With the very best of the city at your doorstep, there are all kinds of adventures for couples to experience together. From outdoor movie nights to private helicopter tours, we curated a list of activities for a romantic rendezvous.

If you’re feeling adventurous, take your date night sky-high. You can enjoy romantic sunset views of the Chicago skyline from a private helicopter. A thirty-minute deluxe tour with Breeze Helicopters offers all the greatest views in Downtown Chicago, in addition to northern attractions like the Baha’i Temple and Northwestern University. You can also enjoy stunning views of the city and Lake Michigan along the Riverwalk or atop the Ferris wheel at Navy Pier. Take a stroll down the Riverwalk and enjoy a wine and cheese plate outside at City Winery. Then, finish the night with a VIP gondola ride on Navy Pier’s Centennial Wheel at sunset.

Fine wine and cuisine are always on the table for date night. Stroll across the Lakeshore East Park and you’ll discover delicious contemporary Greek cuisine at Avli on the Park. With a menu curated by a Grecian executive chef, seasonal rooftop dining, and drinks featuring Greek spirits and bitters, you will get an authentic Greek dining experience. Avli also offers $25 bottomless mimosas every Saturday and Sunday, as well as weekly events. For a more intimate dining experience, opt for a private yacht dinner cruise. Adeline’s Sea Moose offers a personal assistant and discreet crew to ensure every detail is perfect for your romantic dinner on the water.

Bask in summer weather with a picnic in Millennium Park. Only walking distance from The St. Regis Chicago, you can find outdoor film screenings and music festivals all summer long. Pack a charcuterie board and some wine for a picnic followed by a movie under the stars. Chicago’s live entertainment scene is always bustling with new date night opportunities, though. Just across the street from Millennium Park, the Chicago Symphony Orchestra would make for the perfect date for music connoisseurs.

The possibilities are endless for an exhilarating date night in Chicago. Whether you prefer an intimate dinner or a night out on the town, all these experiences are in arm’s reach at The St. Regis Chicago.