| Check the PowerBall jackpot and pick your numbers from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Check the Mega Millions jackpot and pick your numbers from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Check the Lotto jackpot and pick your numbers from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Check the LuckyDay Lotto jackpot and pick your numbers from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Play Pick 3 from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Play Pick 4 from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Win with Instant Tickets from Illinois Lottery » Listings » see also: Gambling Entertainment -- Entertainment | Drawing | |
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| Your opinion for the chance to win $3000 cash from Walgreens on the Vibary » Listings » see also: Pharmacies -- Health | Drawing | |
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| Win free sandwich or cash with Wendy's Satisfaction Survey from Wendy's » Listings » see also: Restaurants -- Food, Entertainment | Drawing | |
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| Enroll for chance to win a $500 gift card from ComEd » Listings » see also: Electric Companies -- Business, Home | Drawing | |
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| Win a Tesla Model X from Illinois Solar Energy Association » Listings » see also: Engineering Companies -- Business, Other | Drawing | |
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| Gift Certificates Sweepstakes from The Balance Everyday » see also: Gift Shops -- Shopping, Personal | Drawing | |
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| Win Free Food with Sweepstakes and Contests from The Balance Everyday » see also: Gourmet Foods -- Food | Drawing | |
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| Electronic Gadgets Sweepstakes from The Balance Everyday » see also: Home Electronics -- Computing | Drawing | |
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| Free iPads and Tablets Sweepstakes from The Balance Everyday » see also: Internet Service Providers -- Computing, Business | Drawing | |
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| Free Computer Sweepstakes from The Balance Everyday » see also: Computer Retail -- Computing, Business | Drawing | |
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| Baking, Cooking and Recipe Contests from The Balance Everyday » see also: Houseware Stores -- Shopping, Home, Food | Drawing | |
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| Jewelry and Fashion Sweepstakes from The Balance Everyday » see also: Jewelers -- Fashion, Personal | Drawing | |
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| Sweepstakes for Kids and Teens from The Balance Everyday » see also: Kid Fashions -- Family | Drawing | |
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| Magazine Sweepstakes for monthly prizes from The Balance Everyday » see also: Magazines -- Automotive, Arts, Entertainment, Home, Computing, , Finance, News, Shopping, Sports | Drawing | |
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| Movie and Concert Tickets Sweepstakes from The Balance Everyday » see also: Music Performance -- Education | Drawing | |
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| Sports, Fitness and Outdoors Sweepstakes from The Balance Everyday » see also: Outdoor Recreation -- Sports | Drawing | |
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| NASCAR Sweepstakes from The Balance Everyday » see also: Car Showing -- Automotive, Hobbies | Drawing | |
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| House and Garden Sweepstakes from The Balance Everyday » see also: Appliance Stores -- Home | Drawing | |
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| House and Garden Sweepstakes from The Balance Everyday » see also: Appliance Stores -- Home | Drawing | |
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| Baby and Children Stuff Sweepstakes from The Balance Everyday » see also: Baby Essentials -- Family | Drawing | |
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| Writing Contests from The Balance Everyday » see also: Bookstores -- Education | Drawing | |
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| Sweepstakes where you can win a car from The Balance Everyday » see also: Car Dealership -- Automotive | Drawing | |
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| New Sweepstakes for You to Enter Right Now from The Balance Everyday » see also: Advertisement Agencies -- Business | Drawing | |
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| Toys and Games Sweepstakes from The Balance Everyday » see also: Toys -- Entertainment, Hobbies | Drawing | |
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| Wedding Sweepstakes and Contests from The Balance Everyday » see also: Wedding Services -- Personal | Drawing | |
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| The Annual Raffle - 2021 Lexus LC 500 convertible from Turning Pointe Autism Foundation » Listings » see also: Disability Services -- Family, Personal, Health | Drawing | |
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| Enter Sweepstakes from Guest Experience Survey from Cinemark Theatres » Listings » see also: Cinema -- Entertainment | Drawing | |
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| AMC Sweepstakes from AMC Theatres » Listings » see also: Cinema -- Entertainment | Drawing | |
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| Marcus Sweepstakes & Contests from Marcus Theaters » Listings » see also: Cinema -- Entertainment | Drawing | |
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| Hungry Home 'Recker Challenge! from Real Urbain Barbecue » Listings » see also: Restaurants -- Food, Entertainment | Other | |
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| Radio Contest - Keep listening for a chance to win! from WGN Radio 720 » Listings » see also: Radio Stations -- Entertainment | Drawing | |
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| BIG 95.5 Radio Contests from BIG 95.5 » Listings » see also: Radio Stations -- Entertainment | Drawing | |
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| 103.5 KISS FM Radio Contests from 103.5 KISS FM » Listings » see also: Radio Stations -- Entertainment | Drawing | |
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| 93.9 LITE FM Radio Contests from 93.9 LITE FM » Listings » see also: Radio Stations -- Entertainment | Drawing | |
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| 101 WKQX Radio Contests from 101WKQX » Listings » see also: Radio Stations -- Entertainment | Drawing | |
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| Use the Park Points to bid on Exclusive Experiences from Chicago Park District » Listings » see also: Parks -- Family, Entertainment | Drawing | |
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| FREEinWKND -- Free Stuff Every Friday from RedEye Chicago » Listings » see also: Newspapers -- News | Drawing | |
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| We love contests from Daily Herald » Listings » see also: Newspapers -- News | Drawing | |
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| 10 Days of Giveaways from Chicago Magazine » Listings » see also: Magazines -- Automotive, Arts, Entertainment, Home, Computing, , Finance, News, Shopping, Sports | Drawing | |
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| Search Bing. Earn Free Rewards from Microsoft Bing Search » see also: Internet Service Providers -- Computing, Business | Drawing | |
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| Fill out our survey for a chance to WIN from RSVP Chicago » Listings » see also: Advertisement Agencies -- Business | Drawing | |
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| Main Stream Movie Sweepstakes from gofobo » see also: Cinema -- Entertainment | Drawing | |
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| Movie Sweepstakes on MovieTickets.com from MovieTickets.com » see also: Cinema -- Entertainment | Drawing | |
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| Movie Sweepstakes on Fandango.com from Fandango.com » see also: Cinema -- Entertainment | Drawing | |
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