Outdoor & Fitness deals in Chicago

28 active deals · Updated July 2, 2026

Best deal Lowest price Biggest savings Newest

Under $25 Under $50 Under $100

Discover Chicago’s Hidden Beauty with Wateriders’ 2-Hour Kayak Rentals for One or Two People

Save 36%

Kayaking Paddleboarding

Discover Chicago’s Hidden Beauty with Wateriders’ 2-Hour Kayak Rentals for One or Two People

$33$51.78Save $18.78View deal →

Adventure Awaits with Wateriders Sunset, Moonlight, Guided Kayak Tours & Rentals in the Heart of Downtown Chicago

Save 30%

Kayaking Paddleboarding

Wateriders Kayak Tours - Kingsbury Location

Adventure Awaits with Wateriders Sunset, Moonlight, Guided Kayak Tours & Rentals in the Heart of Downtown Chicago

★ 4.8

$45$64.50Save $19.50View deal →

Daily Single Kayak Rentals Near Chicago

Kayaking Paddleboarding

Daily Single Kayak Rentals Near Chicago

$89View deal →

Daily Tandem Kayak Rentals Near Chicago

Kayaking Paddleboarding

Daily Tandem Kayak Rentals Near Chicago

$99View deal →

More deals in Chicago

Things to Do156 deals Food & Drink66 deals Tickets & Events10 deals Kids & Family16 deals Beauty & Wellness89 deals Auto & Home16 deals