Past Chicago Contests

Steinhafels Solo Stove Sweepstakes Contest ended on 5/23/24

2024 I-94 Rivalry Roadtrip Sweepstakes Contest ended on 5/19/24

Chelsea v Celtic Ball Kid Sweepstakes Rules Contest ended on 5/10/24

Chelsea v Celtic Flag Bearer Sweepstakes Rules Contest ended on 5/10/24

Chelsea v Celtic Ticket Sweepstakes Contest ended on 5/10/24

Mothers Day Mishaps Contest Rules Contest ended on 5/8/24

2024 Woodford Reserve Distillery Experience Contest Rules Contest ended on 5/5/24

ESPN Chicago Derby 150 Sweepstakes Rules Contest ended on 5/3/24

Derby Day Party Package Sweepstakes Rules Contest ended on 4/26/24

Draft Watch Party with Jurko Sweepstakes Rules Contest ended on 4/25/24

Chicago Bears Draft Party Contest Rules Contest ended on 4/19/24

A Night with Marian Hossa Sweepstakes Contest ended on 4/16/24

Wee Whiskey Fest Sweepstakes Contest ended on 4/12/24

64 Teams, 1 Winner Contest Rules Contest ended on 4/9/24

Taste of The Masters Contest Rules Contest ended on 4/6/24

Xfinity Grand Opening Sweepstakes Contest Rules Contest ended on 4/6/24

Northside Home Opener Sweepstakes Contest Rules Contest ended on 4/1/24

Steinhafels Presidents’ Day Flyaway Contest Rules Contest ended on 2/16/24

Lou Malnati’s Super Pizza Package Contest Rules Contest ended on 2/7/24

Advantage Acura ESPN Chicago Fantasy Football Championship Draft Contest Rules Contest ended on 1/9/24

2023 ESPN Chicago Fantasy Football Championship Contest Rules Contest ended on 1/9/24

Chicago Bears Night in Chicago Contest Rules Contest ended on 1/8/24

Football Feast Sweepstakes Contest Rules Contest ended on 1/5/24

Bud Light Trivia Nights with Shea Norling Contest Rules Contest ended on 12/29/23

PBR Unleash the Beast Sweepstakes Contest Rules Contest ended on 12/17/23

2023 Waddle & Silvy Holiday Parody Contest Rules Contest ended on 12/15/2023

The Champions Classic Ticket Sweepstakes Contest Rules Contest ended on 11/13/2023

Creed Ticket Sweepstakes Contest Rules Contest ended on 11/3/2023

ESPN Chicago Home of the Chicago Bears Sweepstakes Contest Rules Contest ended on 10/22/2023

Football Feast Toast to a Victory Sweepstakes Contest Rules Contest ended on 10/5/2023

Nissan No-Hitter Contest Rules 2023 Contest ended on 10/1/2023

Behind the Scenes with Kap & J.Hood Part 2 Contest Rules Contest ended on 10/1/2023

US Women’s National Soccer Team Sweepstakes Contest Rules Contest ended on 9/20/2023

2023 LIV Golf Sweepstakes Contest Rules Contest ended on 9/19/2023

2023 ESPN Chicago Football Fest Ticket Sweepstakes Contest Rules Contest ended 8/21/2023

ESPN Chicago Bears Training Camp Sweepstakes Contest Rules Contest ended 8/10/2023

PYP Crushed Car Contest Contest Rules Contest ended 8/4/2023

White Claw Windy City Takeover in Kansas City On-Air Contest Rules Contest ended 8/4/2023

White Claw Windy City Takeover in Kansas City Contest Rules Contest ended 7/29/2023

National Sports Collectors Convention Giveaway Contest Rules Contest ended 7/25/2023

Inside the Ropes Contest Rules Contest ended 7/24/2023

Country Thunder VIP Giveaway Contest Rules Contest ended 7/18/2023

SkyTown VIP Experience Giveaway Contest Rules Contest ended 7/10/2023

Dawg Town Block Party Giveaway Contest Rules Contest ended 7/8/2023

2023 ESPN Chicago Honorary ESPY Contest Rules Contest ended 6/23/2023

Chew on This Contest Rules Contest ended 6/23/2023

What Would You Do Contest Rules Contest ended 6/23/2023

2023 Golf Center Golf Giveaway Contest Rules Contest ended 6/19/2023

NASCAR Giveaway Contest Rules Contest ended 6/9/2023

2023 Best Dad Fails Contest Rules Contest ended 6/9/2023

Woodford Reserve Distillery Experience Contest Rules Contest ended 4/21/2023

Skate with Carmen & Jurko Contest Rules Contest ended 3/23/2023

ESPN Chicago’s 25th Anniversary Ticket Giveaway Contest Rules Contest ended 3/17/2023

64 Teams, 1 Winner Contest Rules Contest ended 3/15/2023

Behind the Scenes with Kap & J.Hood Contest Rules Contest ended 3/10/2023

Tip Off the Madness Ticket Giveaway Contest Rules Contest ended 2/24/2023

Spare a Square 2023 Contest Rules Contest ended 2/12/2023

2023 National Pizza Week Pizza Giveaway Contest Rules Contest ended 1/13/2023

Carmen & Jurko Cover5 Contest Rules Contest ended 1/10/2023

PointsBet Pregame Show – The Second Chance Contest Rules Contest ended 1/10/2023

2022 ESPN Chicago Fantasy Football Championship Draft Contest Rules Contest ended 1/6/2023

2022 Shot or No Shot Contest Rules Contest ended 12/16/2022

Best Holiday Fails Contest Rules Contest ended 12/16/2022

2022 Waddle & Silvy Holiday Parody Contest Rules Contest ended 12/9/2022

KJM $10K A DAY GIVEAWAY Contest ended 12/7/2022

Carmen & Silvy Blackhawks Tickets Giveaway Contest Rules Contest ended 12/2/2022

Big 10 Pick ‘Em Challenge Contest Rules Contest ended 11/20/2022

Club Hawthorne Pool Party Contest Rules (Kap) Contest ended 10/20/2022

PointsBet Pregame Show – The Second Chance Contest Rules Contest ended 10/20/2022

Nissan No-Hitter Contest Rules 2022 Contest ended 10/6/2022

White Claw Windy City Takeover in Dallas Bar Crawl Contest Rules Contest ended 10/2/2022

Windy City Takeover in Dallas Contest Rules Contest ended 9/30/2022

Pride Stores Barrel Pick Contest Rules Contest ended 8/31/2022

LKQ Crushed Car Contest Contest Rules Contest ended 8/15/2022

Sagamore Spirit Whiskey University Giveaway Contest Rules Contest ended 7/20/2022

The 2022 ArchnemeSWISS Giveaway Contest ended 7/3/2022

2022 ESPN Chicago Honorary ESPY Contest Rules Contest ended 7/1/2022

2022 My Wife or Radio Partner Contest Rules (ComedySportz) Contest ended 6/29/2022

Best Dad Fails Contest Rules Contest ended 6/17/2022

Cover5 ESPN Chicago Playoff Hoops Contest Rules Contest ended 6/20/2022

MLB The Show Giveaway Contest Rules Contest ended 4/22/2022

MLB The Show 22 Trivia Giveaway Contest Rules Contest ended 4/22/2022

CDGA Golf Show Zero Friction Giveaway Contest Rules Contest ended 4/17/2022

GKB Cover5 Madness 16 Contest Rules Contest ended 3/25/2022

GKB Cover5 Madness Contest Rules Contest ended 3/21/2022

68 Teams, 1 Cup Contest Rules 2022 Contest ended 3/16/2022

Shot or No Shot Contest Rules 2022 Contest ended 3/4/2022

Would You Rather Contest Rules 2022 Contest ended 2/9/2022

AEW Ticket Giveaway Contest Rules Contest ended 1/27/2022

What’s At Steak Contest Rules 2022 Contest ended 1/24/2022

Frank Caliendo Ticket Giveaway Contest Rules Contest ended 1/19/2022

My Wife or Radio Partner Contest Rules 2022 Contest ended 1/19/2022

National Pizza Week Pizza Giveaway Contest Rules Contest ended 1/14/2022

Waddle & Silvy Twin Peaks Giveaway Contest Rules Contest ended 1/14/2022

2021 Waddle & Silvy Holiday Parody Contest Rules Contest ended 12/17/2021

The Grate Cheesy Giveaway (Nov, Dec) – Contest Rules 2021 Contest ended 12/12/2021

Chicago’s College Tailgate Gift Card Giveaway Contest Rules Contest ended 12/4/2021

Waddle Watch Party Giveaway Contest Rules Contest ended 11/8/2021

Bleck & Abdalla Watch Party Ticket Giveaway Contest Rules Contest ended 11/6/2021

Whiskey University Gift Card Giveaway Contest Rules Contest ended 11/10/2021

ESPN Chicago PointsBet Pregame Giveaway Contest Rules Contest ended 1/9/2022

Free Pizza Friday Giveaway Contest Rules Contest ended 10/29/2021

It’s Miller Time Cooler Giveaway Contest Rules Contest ended 12/3/2021

Big 10 Championship Trip Giveaway Contest Rules Contest ended 11/19/2021

Jason Bonham’s Led Zeppelin Evening Ticket Giveaway Contest Rules Contest ended 10/13/2021

Chicago Wolves Ticket Giveaway Contest Rules Contest ended 10/16/2021

Playoff Gift Card Giveaway Contest Rules Contest ended October, 2021

Windy City Takeover in Vegas Contest Rules Contest ended 9/20/2021

ESPN Chicago Golf Outing Enter to Win Contest Rules Contest ended 9/14/2021

Windy City Takeover in Vegas Bar Crawl Contest Rules Contest ended 9/18/2021

Monster Jam Ticket Giveaway Contest Rules Contest ended 9/9/2021

Run Your Sox Off 5k Giveaway Contest Rules Contest ended 9/8/2021

Where Are They Now Contest Rules Contest ended 8/26/2021

#ESPNFanCamp Contest Rules Contest ended 8/25/2021

Giving Small Business a Big Future 2021 Contest ended 8/22/2021

Free Ticket Friday Contest Rules Contest ended 9/17/2021

The Grate Cheesy Giveaway – Contest Rules 2021 Contest ended 7/23/2021

2021 ESPN Chicago Fantasy Football Championship Contest Rules Contest ended 8/21/2021

National Sports Collectors Convention Ticket Giveaway Contest Rules Contest ended 7/19/2021

Show Us Your Dash Contest Rules Contest ended 10/15/2021

Meat and Greet with Jurko Contest Rules Contest ended 7/1/2021

Kane County Fair Ticket Giveaway Contest Rules Contest ended 6/28/2021

I-94 Rivalry Roadtrip Rules Contest ended 6/21/2021

Kap & J.Hood City Connect Jersey Giveaway Contest Rules Contest ended 6/9/2021

City Connect Jersey Giveaway Contest Rules Contest ended 6/8/2021

Freaky Fast Trivia Rules Contest ended 5/10/2021

White Sox Ticket Giveaway Contest Rules Contest ended 4/8/2021

Opening Day White Sox Trivia Contest Rules Contest ended 4/1/2021

Hometown Hockey Giveaway Contest Rules Contest ended 2/20/2021

Coors Light Game Face Contest Rules Contest ended 2/7/2021

Waddle & Silvy Spare a Square Contest Rules Contest ended 2/3/2020

Giving Tuesday’s Ultimate Giveaway Contest ended 2/7/2021

Waddle & Silvy Holiday Parody Contest Rules Contest ended 12/16/2020

ArchnemeSWISS Giveaway – Contest Rules 2020 Contest ended 11/29/2020

The Last Dance Blu-ray Giveaway Contest Rules Contest ended 11/10/2020

PointsBet Pregame Call to Win Contest Rules Contest ended 1/4/2021

It’s Miller Time in Chicago Contest Rules Contest ended 1/3/2021

Great Clips 20 Greatest Bears Players Contest Rules Contest ended 12/10/2020

Quarterback Carousel Contest Rules Contest ended 9/11/2020

Battle of the Reporters Contest Rules Contest ended 9/2/2020

Season of the Southsiders Contest Rules Contest ended 10/1/2020

Chicago’s Best Baseball Bars Contest Rules Contest ended 10/3/2020

The Skrewball Sign-Off Contest Rules Contest ended 1/1/2021

Miller Lite Fantasy Football Championship 2020 Contest Rules Contest ended 8/23/2020

Silvy Strong Challenge Contest Rules Contest ended 8/31/2020

Great Clips 20 Greatest Cubs Players Contest Rules Contest ended 9/17/2020

Made to Chill Contest Rules Contest ended 8/14/2020

Ultimate Home Tailgate Contest Rules Contest ended 8/28/2020

Woodbridge Heroes Contest Rules Contest ended 9/27/2020

ESPN Chicago Honorary ESPY Contest Rules Contest ended 6/16/2020

Ultradad Giveaway Contest Rules Contest ended 6/21/2020

Golf with Jurko Contest Rules Contest ended 5/31/2020

The Game – Ultimate Loser Edition Contest Rules Contest ended 5/6/2020

Waddle & Silvy Talent Contest Rules Contest ended 4/24/2020

The Game – Tourney of Champions Contest Rules Contest ended 4/17/2020

The Biggest Name Drop Contest Rules Contest ended 4/3/2020

The Way Back Screening Contest Rules Contest ended 3/2/2020

Follow the Northsiders to England Contest Rules Contest ended 3/6/2020

D. Wade Life Unexpected Screening Contest Rules Contest ended 2/18/2020

Great Clips 20 Greatest Players Rules Contest ended 3/20/20

Waddle & Silvy Spare a Square Detailed Contest Rules Contest ended 2/3/2020

Crawl to Spring Training Rules Contest ended 2/19/2020

Cover 2 Contest ended 12/16/2019