Seasonal Deals in Chicago — 381 deals

Immerse Yourself in Mystery: Private Escape Room Experience at Combat Chicago (Up to 37% Off)

Up to 50% Off on Automotive Window Tinting at Chicagos Tint Studio

Oh My Goodness Soul Eatery

Up to $50 to spend on soul food and more at Oh My Goodness Soul Eatery, Up To 50% Off

★ 4.4 · 778 reviews

Pure Serenity Spa

60-minute Tailored Deep-Tissue or Swedish Massage with Couples Option at Pure Serenity Spa (Up to 37% Off)

★ 4.8 · 5,144 reviews

Elements Massage South Loop

Massage or Facial Packages: Single or Multi-Session Options at Elements Massage South Loop(Up To 41% Off)

★ 4.6 · 402 reviews

Conquer the Bullseye: Axe Throwing Thrills Await at Black Oak Axe Throwing at Combat Chicago (Up to 40% Off)

Skydive Windy City - Michigan City, IN

Experience Stunning Views of Lake Michigan and the Chicago Skyline From Above w/ Tandem Skydive Jump for 1 to 4

★ 4.9

Chicago R&B Rodeo Southern Style Food Music Festival Chicago 2026

Chicago R&B Rodeo: Southern Style Food & Music Festival on July 25

Partake NYC and HK Hall - New York

Best of Both Cities: Chicago & New York Takeover w/ DJ Sean Mac, Joe Global, & more on July 10-11 at 10 PM

Get Smooth with One 15-minute or 30-minute Electrolysis Hair Removal Session at Cassie Electrolysis Up To 27%Off)

One-Way Trip Premier SUV for Up to 4 Passengers or Round Trip from Downtown Chicago to Airports (Up to 33% Off)

Heavenly Massage

Unwind with a Swedish or Deep-Tissue Massage, Enhanced by Aromatherapy & CBD Oil for Solo or Couples

★ 4.6 · 19,516 reviews

Experience Leah Chavie Skincare Boutiques Hydrafacial Options, 3-Pack or Single Treatment, with up to 26% Off

Discover Chicagos Rich LGBTQ History & Culture on a Guided Bus Tour for One, Two or Four People

Panic Escape Room - Chicago

Escape Room Challenge for 4–10 People at Panic Escape Room

Chicago Ghosts and Gangsters Tours - Chicago, IL

Choose Your Adventure: Ghost Walking Tour, Food Tasting Tour, or Minibus Tour Exploring Historic & Haunted Sites

Pure Medical Spa

Unlock Timeless Beauty with One or Two Syringes of Juvéderm Ultra XC at Pure Medical Spa (Up to 31% Off

Create Joyful Memories for Your Kids with Indoor Play & Unique Birthday Parties at Early Bird Play Cafe

Discover Chicagos Hidden Architectural Wonders: Secret Interiors Walking Tour

Dive into Great Chicago Fire Brewerys beer flights and pints packages for two or four, with up to 30% off on an authentic experience

Walkin with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Explore Chicagos Rich Maritime History with Admission for 2, 3, 4, or 6 People to the Chicago Maritime Museum

The Rabbit Hole Offers $20 or $40 Towards Food and Drink Experience in Chicago (Up to 28% Off)

Fly Heli Chicago IL

Soar Above the Skyline: Experience Chicagos Iconic Landmarks on a Helicopter Tour

★ 4.6