Feel the Love: Romantic Things to Do in Chicago on Valentine's Day
What does romance mean to you? A cozy cocktail lounge or a crack-up comedy club? Ice skating in the park or dancing in the dark? Discover a delightful array of romantic shows, attractions, and quirky things to do on Valentine’s Day in Chicago this year.
Cabaret, Comedy, and Cocktails in Chicago
Valentine’s Day falls on Wednesday, February 14 – but you can celebrate the holiday all month long.
- The Naked at the Art Museum Scavenger Hunt (February 10) – Search the Art Institute of Chicago for provocative art pieces.
- Cocktails at Cityscape – Chill out with artisan cocktails and unbeatable skyline views at our rooftop bar.
- Outdoor Ice Skating (ongoing) – Find romantic ice rinks at Millennium Park, Maggie Daley Park, and Wentworth Park.
- Chicago Botanic Garden Orchid Show (ongoing) – Indulge in classic romance with 10,000 orchids at this amazing flower show.
- Cupid’s Undie Run (February 10) – Put on your skivvies and dash through Wrigleyville.
- Hooking Up with the Second City at UP Comedy Club (ongoing) – Laugh at improv skits inspired by modern dating and love.
- Kiss Kiss Cabaret (ongoing) – This risqué group merges comedy, music, and burlesque dancing in their improv show.
Chicago Valentine’s Day Getaway in River North: Romance Package
Make your escape this month and plan a romantic getaway to our charming hotel. Book our Romance Package and treat yourself to stylish accommodations, overnight parking, and chocolate-covered strawberries, sparkling wine, and breakfast delivered to your guestroom. Book your Valentine’s Day getaway today!