Seasonal Deals in Chicago — 381 deals

City Cruises Chicago - Signature Dining

Lake Michigan Signature Dining Cruises with City Cruises

★ 4.4

50-Minute Massage or Facial (for One or Couples) with Up to 25% Off

Experience Tactical Laser Tag at Combat Chicago

City Cruises Chicago Premier Brunch, Lunch, Dinner, or Fireworks Dinner Cruise

Heavenly Massage Solo or Couples

Massage + Facial Package at Heavenly Massage — Solo or Couples, 60 or 90 Minutes (Up to 22% Off)

Artango Bar & Steakhouse

Savor Argentina in Chicago: Experience an Authentic Atmosphere at Artango Bar and Steakhouse

Indulge in Chicago Chiropractic & Sports Injury Centers Massage Options: Cupping or laser therapy Up To 40% Off

Chicago Premier Plus Brunch, Lunch & Dinner Cruise Deals with City Cruises

Bike and Roll Chicago- Chicago, IL

Glide Along Chicagos Lakefront on a Highly-Reviewed Guided Segway Tour for One, Two or Four - Through (13/09/2026)

Join Latin Street Music & Dancing for unlimited dance classes, explore salsa, bachata and more with up to 30% off

Experience Chicago Handshake for 2 or 4 People, General Spend for $25 or $50 at EZ Inn (Up to 30% Off)

4-Session Wine-Making Classes for 2 (Valid Monday, Thursday, and Friday) at Bev Art Inc Chicago (Up to 21% Off)

Transform your Fitness with 5 Aerial Yoga / Fitness Classes in Chicago for a Full Body Workout

The Spa at Trump Chicago

Luxury Spa Day with Pool Access at The Spa at Trump Chicago: 60 or 90 Minute Massage, Facial, Both or Couples, Up to 28%

★ 4.8 · 409 reviews

City Cruises - Chicago Architectural Tour

Chicago Seadog River and Lake Architectural Tour at City Experiences

City Cruises - Chicago Seadog Lakefront

Chicago Seadog Lakefront Speedboat Cruise with City Cruises

City Cruises - Chicago Seadog

Chicago Seadog Extreme Thrill Ride at City Cruises

Wings & Pizza Feast: Choose from Wings, Specialty Pizzas & More at Chicagos Pizza Twist (Up to 20% Off)

See Chicago from the Water: 45-Minute Seadog Architecture Tour on the River - Save 20%

Chicago Architecture River Cruise

Pho Home offers up to 20% off on food and drink vouchers, perfect for groups or solo diners in Chicago

Up to 33% Off on RF Skin Tightening at Skinovatio Lincoln Park

Step into Private Chicago Steppin Classes for Singles, Couples and Older at Fox Meadows (Up to 20%Off)

Enjoy a 45-minute scenic flight with Chicago Aerial Tours by Zain Aviation, up to 20% off; Restrictions Apply