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Fall Activities » Outdoor Fun

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            Trending
            St. Julian Winery
            9145 Union Pier Road • 49.1 mi
            4.8
            4.8 stars out of 5 stars
            2172 Ratings
            Regular price $12
            $12
             
            Discount price $7.50
            $7.50
            38% OFF
            Wine Tasting for one person
            View Deal
            • Trending
              Tours and Boats - Architecture Tour - Chicago
              900 South Wells Street, Chicago • 0.8 mi
              4.8
              4.8 stars out of 5 stars
              8707 Ratings
              Regular price $49
              $49
               
              Discount price $29
              $29
              41% OFF
              $29 for 90-Minute Chicago Architecture Boat Tour for One
            • Trending
              Suburbanite Bowl
              201 W Ogden Ave., Westmont • 19.1 mi
              4.8
              4.8 stars out of 5 stars
              1259 Ratings
              Regular price $49
              $49
               
              Discount price $26
              $26
              47% OFF
              1 Hour of Bowling on 1 Lane with Shoe Rentals for Two and 2 Free Game Coupons for Your Next Visit
            • VIN312 Winery
              4710 North Ravenswood Avenue, Chicago • 6.6 mi
              4.9
              4.9 stars out of 5 stars
              175 Ratings
              Regular price $50
              $50
               
              Discount price $43
              $43
              14% OFF
              Tasting and One Bottle of Red or White Wine for One
            • LIV Golf Chicago
              2001 Rodeo Drive, Bolingbrook • 30.8 mi
              Regular price $35.10
              $35.10
               
              Discount price $24.57
              $24.57
              30% OFF
              Friday Grounds Pass to LIV Golf Chicago (8/8/25)
              6 bought
            • True Motion Golf
              4.9
              4.9 stars out of 5 stars
              9 Ratings
              Regular price $297
              $297
               
              Discount price $178
              $178
              40% OFF
              3-Months Unlimited Golf Lessons
            • Chicago Cruise Events
              200 North Breakwater Access, Chicago • 0.8 mi
              4.4
              4.4 stars out of 5 stars
              3419 Ratings
              Regular price $32
              $32
               
              Discount price $12
              $12
              63% OFF
              Monday or Tuesday Night Sunset Skyline Cruise for One
            • White Pine Winery
              317 State Street, Saint Joseph
              4.6
              4.6 stars out of 5 stars
              293 Ratings
              Regular price $24
              $24
               
              Discount price $14.40
              $14.40
              40% OFF
              Wine Tasting for Two
            • Skydive Windy City
              1300 S Indiana Highway 212, Michigan City • 43 mi
              4.9
              4.9 stars out of 5 stars
              1793 Ratings
              Regular price $279
              $279
               
              Discount price $203
              $203
              27% OFF
              Tandem Skydive Jump for One
            • iFLY
              1752 Freedom Dr., Naperville • 26.4 mi
              4.8
              4.8 stars out of 5 stars
              214 Ratings
              Discount price $94
              $94
              Two Flights for One Person
            • D'Vine Wine And Gifts
              243 East Northwest Highway, Palatine • 26.9 mi
              4.7
              4.7 stars out of 5 stars
              501 Ratings
              Regular price $50
              $50
               
              Discount price $32
              $32
              36% OFF
              Wine And Popcorn Tasting For 2 With Take Home Bottle of Wine And Bag Of Popcorn
            • Fly Heli
              1339 South Wood Street, Chicago • 2.6 mi
              4.8
              4.8 stars out of 5 stars
              15 Ratings
              Regular price $375
              $375
               
              Discount price $338
              $338
              10% OFF
              The Chicago Helicopter Tour 12 Miles (Up to 3 Passengers)
            • 10 Pin Lounge
              330 North State Street, Chicago • 0.6 mi
              4.8
              4.8 stars out of 5 stars
              473 Ratings
              Regular price $60
              $60
               
              Discount price $38
              $38
              37% OFF
              One-Hour of Bowling with Shoes for Two
            • CHICAGO LUXURY CRUISES
              400 East Monroe Street, Chicago • 0.4 mi
              Regular price $60
              $60
               
              Discount price $35
              $35
              42% OFF
              Skyline Boat Cruise For One Person
            • iFLY
              800 W Scott St., Chicago • 2.2 mi
              4.6
              4.6 stars out of 5 stars
              194 Ratings
              Discount price $94
              $94
              Two Flights for One Person
            • Schaumburg Boomers Baseball 2025
              1999 S Springinsguth Rd., Schaumburg • 26.6 mi
              Regular price $32
              $32
               
              Discount price $24
              $24
              25% OFF
              2 Reserved tickets to Any Home Game
              560+ bought
            • City Cruises - Chicago Architectural Tour (NBC Tower)
              455 North Cityfront Plaza Drive, Chicago • 0.7 mi
              4.4
              4.4 stars out of 5 stars
              2916 Ratings
              Regular price $55.88
              $55.88
               
              Discount price $46.49
              $46.49
              17% OFF
              Seadog Architecture Tour
            • Raymond's Bowl & Entertainment Center
              3960 North Johnsburg Road • 46.8 mi
              4.9
              4.9 stars out of 5 stars
              1079 Ratings
              Regular price $61
              $61
               
              Discount price $35
              $35
              43% OFF
              60-Minute Bowling Package for Two with Shoe Rental and Two Medium Sodas or Two Pints of Domestic Beer
            • Prāzbar
              5.0
              5.0 stars out of 5 stars
              1 Rating
              Regular price $49.99
              $49.99
               
              Discount price $35.99
              $35.99
              28% OFF
              Non-Alcoholic Wine Pairing Party
            • Skydive Midwest
              13851 56th Road, Sturtevant
              4.9
              4.9 stars out of 5 stars
              1231 Ratings
              Regular price $299
              $299
               
              Discount price $219
              $219
              27% OFF
              One Tandem Skydiving Jump for One Person (Ages 18+), Valid Monday - Friday
            • Kane County Cougars 2025
              34w002 Cherry Lane, Geneva • 33.9 mi
              Regular price $29
              $29
               
              Discount price $12
              $12
              59% OFF
              Minor-League Baseball Games
              710+ bought
            • Valentino Vineyards & Winery
              5175 Aptakisic Rd., Long Grove • 27.7 mi
              4.2
              4.2 stars out of 5 stars
              483 Ratings
              Regular price $49
              $49
               
              Discount price $28
              $28
              43% OFF
              Tour & Wine-Appreciation Seminar
            • Punch Bowl Social Chicago
              310 North Green Street, Chicago • 1.4 mi
              5.0
              5.0 stars out of 5 stars
              12 Ratings
              Regular price $75
              $75
               
              Discount price $54.50
              $54.50
              27% OFF
              1.5hrs of Bowling for Two People, Free Shoe Rental (Sales Tax Included)
            • Kayak Chicago
              1220 W. LeMoyne Ave., Chicago • 2.7 mi
              4.8
              4.8 stars out of 5 stars
              1365 Ratings
              Regular price $90.85
              $90.85
               
              Discount price $64
              $64
              30% OFF
              1 Person: Sunset, Bonfire & S’mores Kayaking Tour [Online Reservation Required]
            • First Lady Cruises
              112 East Wacker Drive, Chicago • 0.6 mi
              4.6
              4.6 stars out of 5 stars
              151 Ratings
              Discount price $45
              $45
              Creepy Cruise Tickets
            • The Forge Adventure Park at Lemont Quarries
              227 Heritage Quarries Dr, Lemont • 23.6 mi
              4.7
              4.7 stars out of 5 stars
              357 Ratings
              Regular price $55
              $55
               
              Discount price $45
              $45
              18% OFF
              Explorer Day Pass for One, Valid until October 26
            • Swing Loose Indoor Golf
              2000 Center Drive, Hoffman Estates • 29.2 mi
              4.7
              4.7 stars out of 5 stars
              3 Ratings
              Regular price $80
              $80
               
              Discount price $45
              $45
              44% OFF
              One-Hour Golf Simulator Bay Rental for Up to Six and Club Rentals
            • Chicago White Sox 2025
              333 West 35th Street, Chicago
              Regular price $28.13
              $28.13
               
              Discount price $11.20
              $11.20
              60% OFF
              Chicago White Sox
              1,000+ bought
            • Offshore Adventures
              400 E Monroe St., Chicago • 0.4 mi
              4.3
              4.3 stars out of 5 stars
              735 Ratings
              Regular price $600
              $600
               
              Discount price $199
              $199
              67% OFF
              Private Boat Tour
            • First Lady Cruises
              112 East Wacker Drive, Chicago • 0.6 mi
              4.6
              4.6 stars out of 5 stars
              151 Ratings
              Discount price $45
              $45
              Cruise
            • Wateriders Kayak Tours - Kingsbury Location
              500 N Kingsbury St., Chicago • 1.1 mi
              4.8
              4.8 stars out of 5 stars
              978 Ratings
              Regular price $57.50
              $57.50
               
              Discount price $39
              $39
              32% OFF
              Sunset Paddle Tour for 1 Person
            • LTD Charters
              400 East Monroe Street, Chicago • 0.4 mi
              1.0
              1.0 star out of 5 stars
              1 Rating
              Regular price $1,500
              $1,500
               
              Discount price $1,200
              $1,200
              20% OFF
              Boat Party
            • Superior Training
              7580 South Quincy Street, Willowbrook • 18.7 mi
              4.8
              4.8 stars out of 5 stars
              62 Ratings
              Regular price $30
              $30
               
              Discount price $19
              $19
              37% OFF
              Two 50-Minute Lap-Swimming Sessions (Ages 16 and Up)
            • Chicago Tiki Boat Inc.
              Monroe Harbor, Chicago • 0.4 mi
              4.6
              4.6 stars out of 5 stars
              45 Ratings
              Regular price $1,451.97
              $1,451.97
               
              Discount price $670
              $670
              54% OFF
              Three-Hour Tiki Boat Cruise; Valid Monday–Thursday
            • Lake Katherine Nature Ctr/Botanic Garden
              7402 West Lake Katherine Drive, Palos Heights • 16.7 mi
              4.5
              4.5 stars out of 5 stars
              1020 Ratings
              Regular price $10
              $10
               
              Discount price $7.50
              $7.50
              25% OFF
              Holiday Pre-Sale 1-Hour kayaking on Lake Katherine for One
            • ClimbZone - Chicago
              2500 West Bradley Place, Chicago • 6 mi
              4.9
              4.9 stars out of 5 stars
              317 Ratings
              Regular price $31.99
              $31.99
               
              Discount price $25.60
              $25.60
              20% OFF
              ClimbZone
            • Shoreline Sightseeing
              401 N. Michigan Ave, Chicago • 0.6 mi
              4.9
              4.9 stars out of 5 stars
              3475 Ratings
              Discount price $32.50
              $32.50
              Chicago River Boat Cruises
            • Trending
              Wicked Ball
              332 Yorktown Shopping Center, Lombard • 20.1 mi
              4.5
              4.5 stars out of 5 stars
              287 Ratings
              Regular price $10
              $10
               
              Discount price $7
              $7
              30% OFF
              One Walk-In Game for One Person (Valid Friday-Sunday)
            • Dive Right In Scuba
              16336 South 104th Avenue, Orland Park • 20.7 mi
              5.0
              5.0 stars out of 5 stars
              12 Ratings
              Regular price $80
              $80
               
              Discount price $40
              $40
              50% OFF
              Discover Scuba Diving
            • Homewood Flossmoor Ice Arena
              777 Kedzie Ave, Homewood • 23.2 mi
              4.6
              4.6 stars out of 5 stars
              187 Ratings
              Regular price $10
              $10
               
              Discount price $7
              $7
              30% OFF
              Open Skate Admission and Skate Rental for 1
            • Tall Ship Windy
              600 E Grand Ave., Chicago • 1.2 mi
              4.6
              4.6 stars out of 5 stars
              4339 Ratings
              Regular price $34
              $34
               
              Discount price $25.50
              $25.50
              25% OFF
              75-Minute Skyline Sail for 1 Child (age 1-12) - Valid for Trips August 4 - Sept. 28, 2025 [Online Redemption Required]
            • Wateriders Kayak Tours
              3057 North Rockwell Street, Chicago • 5.3 mi
              4.7
              4.7 stars out of 5 stars
              91 Ratings
              Regular price $51.78
              $51.78
               
              Discount price $33
              $33
              36% OFF
              2-Hour Kayak Rental for 1 Person
            • Chicago Sailboat Charters
              400 West Belmont Harbor Drive, Chicago • 4.5 mi
              4.7
              4.7 stars out of 5 stars
              76 Ratings
              Regular price $920
              $920
               
              Discount price $249
              $249
              73% OFF
              Sailing
            • Wines for Humanity
              Regular price $250
              $250
               
              Discount price $55
              $55
              78% OFF
              In-Home Wine Tasting
              380+ bought
            • The Rink
              1122 E 87th St., Chicago • 10 mi
              4.8
              4.8 stars out of 5 stars
              95 Ratings
              Regular price $36
              $36
               
              Discount price $29
              $29
              19% OFF
              One Skate Lesson with Rental and Open Skate for three
            • Enterrium
              2 Woodfield Mall, Schaumburg • 24 mi
              4.5
              4.5 stars out of 5 stars
              558 Ratings
              Regular price $30
              $30
               
              Discount price $25
              $25
              17% OFF
              For Two: One Hour of Bowling with Shoes; Valid Sunday to Thursday
            • Wateriders Kayak Tours
              1200 West 35th Street, Chicago • 3.8 mi
              4.9
              4.9 stars out of 5 stars
              29 Ratings
              Regular price $48.51
              $48.51
               
              Discount price $33
              $33
              32% OFF
              For One: 2-Hour Kayak Rental
            • Forteza Fitness Physical Culture and Martial Arts
              4437 North Ravenswood Avenue, Chicago • 6.3 mi
              5.0
              5.0 stars out of 5 stars
              98 Ratings
              Regular price $140
              $140
               
              Discount price $94.99
              $94.99
              32% OFF
              Four-hour archery beginner's course for one person
            • Grayslake Park District
              2150 North Drury Lane, Grayslake • 40.4 mi
              4.8
              4.8 stars out of 5 stars
              881 Ratings
              Regular price $19
              $19
               
              Discount price $16
              $16
              16% OFF
              For One: 9-Hole Round of Golf Including Pull Cart
            • Showtime Farms
              2604 280th Avenue, Salem
              4.9
              4.9 stars out of 5 stars
              153 Ratings
              Regular price $75
              $75
               
              Discount price $56.25
              $56.25
              25% OFF
              One Horseback Riding Lesson for One Person
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