Valentine’s Day is just around the corner, and since it falls on a Saturday this year… we’re making it a full weekend of romance. 💘 From dreamy spa dates to skyline views and candlelit concerts, here are the most romantic things to do in Chicago for...
If romance had a temperature, this would be it. Candle-lit thermal pools, ancient bath rituals, and optional couples massages.
Perfect for a slow, sensual reset together.
AIRE Ancient Baths Chicago
See the city lit up from above skyline, lakefront, all of it.
This is the kind of experience that feels cinematic and unforgettable (especially at sunset or night).
Downtown Chicago Helicopter & Aerial Tours
Live classical music in intimate, candle-filled venues. Think romantic ambiance without feeling stuffy perfect if you want something elevated but cozy.
UPCOMING EVENTS
Seasonal illuminated walk through the gardens. Cold? Yes. Romantic? Absolutely. Bundle up, grab hot cocoa, hold hands.
Lightscape
Classic, playful, and low-pressure.
Great if you want something cute and nostalgic instead of overly formal.
Maggie Daley Park Ice Skating Ribbon
Live Jazz at Green Mill
Dim lights, history, live jazz, strong drinks. Perfect for couples who love old-school romance and moody vibes.
The Green Mill
Weekend Escape to Starved Rock Lodge
Just outside Chicago fireplaces, winter hikes, cozy lodge energy.
Feels like a mini-vacation without needing a plane ticket.
Starved Rock Lodge and Conference Center
If AIRE is booked (it will be), this is a luxe alternative. Hydrotherapy, relaxation pools, and a very “treat yourselves” vibe.
Kohler Waters Spa at Lincoln Park: Luxury Spa & Massage in Chicago
A candle-lit dinner while drifting past the skyline. Ideal if you want romance and an activity built in.
Dinner Cruise Chicago River
Private wine tasting. Perfect for couples who want conversation, connection, and good pours.
