There’s no better place for romance than Chicago. We’ve got all the big city glitz and glamour, plus candle-lit restaurants, cozy hotels, and one-of-a-kind date night activities. Come fall in love with Chicago.
Chicago styleCouple's trip
Plan a Chicago date night
Make it a perfect Chicago date night with candlelit dinners, fireworks cruises, and show-stopping entertainment.
Enjoy a bucket list meal
There's nothing more romantic than dinner at the perfect restaurant. Discover places with waterfront views, moody ambiance, and award-winning cuisine.
Create unforgettable memories
Impress your date with these only-in-Chicago experiences, from soaring views to intimate museums.
Fall in love with an inclusive city
Chicago loves love, which means we're a welcoming haven for all couples. Explore top LGBTQ+ attractions and nightlife.
Make it a weekend getaway
Turn date night into a weekend away in the city, complete with a stay at a top hotel.
Find your own adventure
From rock climbing with a view to paddle boarding at the beach, Chicago is a match made in heaven for adventure-seeking couples.
Clayton Hauck for Choose Chicago
Explore hotels, flights, deals, and more
Plan your trip
