A Romantic Day Out In Chicago

A Romantic Day Out In Chicago

Skipping through the Windy City with a loved one? From luxe pampering to romantic riverside cocktails, we have the perfect day in store for you and your beau.

There’s no breezier way to view Chicago’s best asset – Great Lake Michigan – than from the zippy vantage of a bicycle. Fitfluencers can achieve #couplegoals with a bracing morning ride along the breathtaking Chicago Lakefront Bicycle Trail, a whopping 22 miles of cycle paths stretching from Indiana to Evanston, via beaches and parks including Jackson, Grant, Millennium, and Lincoln. Simply download the Divvy Bikes’ app to locate your nearest docking station and straddle one of its sturdy rides, complete with adjustable seat, bell, basket and lights.

Helmet hair not your scene? Kick back for a relaxing river cruise, taking in the city’s jawdropper architecture from the open-top comfort of Chicago's First Lady. Led by the Chicago Architecture Foundation’s docent guides, this insightful 90-minute jaunt tells the story of the historic buildings that transformed Chicago from rustic wallflower to gutsy Deco dame in just 100 years. Opt for the twilight tour to add some romantic sparkle.

You’ve both earned a decompression session, so make for the darkly dapper AIRE Ancient Baths, a River West warehouse turned cavernous candlelit water spa. Ancient Greek, Roman and Ottoman bathing rituals are embraced via hammam, warm, hot and cold plunges, steam room, jet and salt baths, and dreamy aromatherapy massage. The blessed ‘silence policy’ makes for a particularly relaxing interval.

Now, wrap up warm for cuddles and cocktails on the boho-chic patio of Beatnik On The River, showcasing root-to-leaf-tip mixology, before nipping upstairs to sister establishment Café Bonhomme for Med-ish yumminess including tuna tataki, jamon Iberico-wrapped scallops, and huevos rotos with chorizo.

Almost time to retire to your luxuriant suite at The Peninsula, but not before you’re indulged in a nightcap or two at Dorian's, a moody cocktailer tucked behind a record shop, riffing on the moody jazz clubs of the 1960s. Cin cin!

Lakefront Trail / Lake Shore Dr / Divvy Bikes / locations across town / divvybikes.com

Chicago's First Lady / Chicago Riverwalk (look for the blue awning) / N Michigan Ave & E Upper Wacker Dr / +1 847 358 1330 / approx every hr / architecture.org

AIRE Ancient Baths / 800 West Superior St / +1 312 312 9610 / 9am-9pm Tues-Thurs, 8am-9pm Fri-Mon / beaire.com

Beatnik On The River & Café Bonhomme  / 180 N Wacker Dr / +1 312 526 3345 / no res / 11am-11pm Mon, 11am-12am Tues-Fri, 10am-12am Sat, 10am-11pm Sun / beatnikontheriver.com  & cafebonhomme.com

Dorian's  / 1939  W North Ave / +1 773 687 9824 / 6pm-1am Sun-Thurs, 6pm-2am Fri-Sat / throughtherecordshop.com