Best Date Night Ideas in Chicago, IL
Romantic, memorable, and low-key date ideas in Chicago, IL — intimate shows, wine tastings, jazz nights, and weekend experiences worth planning around.
Editor's picks in Chicago, IL
Fri, Oct 9 · 8:00 AM
Marathon Weekend Run/Walk with NOBULL, Laura Green & Erica Kennedy
Happy Monday Coffee - River North, Chicago, IL
Price unavailable — check official source
Fri, Oct 9 · 6:00 PM
Paris with Purpose - Cancer Benefit & Scholarship Dinner
Malcolm X College, Chicago, IL
Price unavailable — check official source
Fri, Oct 9 · 7:00 PM
Jerry Seinfeld
The Chicago Theatre, Chicago, IL
Price unavailable — check official source
Fri, Oct 9 · 7:00 PM
Pre-Season: Chicago Bulls v Memphis Grizzlies
United Center, Chicago, IL
Price unavailable — check official source
Fri, Oct 9 · 8:00 PM
The Dead Bolts with Cab Ellis
Thalia Hall, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 8:00 AM
Shakeout Run & Recovery Lounge presented by Molecule
Lincoln Park Grove 2, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 8:00 AM
Arc'teryx Chicago Marathon Shakeout Run
Arc'teryx Rush Street, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 8:00 AM
Chicago Marathon Shakeout: Shut Up & Run Club x Skull House Running Co
Dialtone Coffee & Wine Bar, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 9:00 AM
SPRINTS Official Chicago Shakeout and Party
Lakefront Trail, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 10:30 AM
2026 Healing Arts Chicago: An Arts x Health x Wellness Summit
Malcolm X College, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 11:00 AM
Gold Coast Walking Tour
Holy Name Cathedral, Chicago, IL
Price unavailable — check official source
Sat, Oct 10 · 11:30 AM
The Rock and Roll Playhouse plays Music of Grateful Dead for Kids
Thalia Hall, Chicago, IL
Price unavailable — check official source