| Contest Name | Contest Winner | Date of Win |
| You Pick-It Fence – $3500 fence from Green T Services | Daniel Silkorski | 1/19/2021 |
| Miracle Method Easy Step | Diane Reynolds | 5/13/2021 |
| Visit Bloomington Indiana Road Trip Getaway (ARV: $700) | Margaret Burroughs | 9/8/2021 |
| Traverse City, MI: Chateau Chantal package | Barbara Span | 9/16/2021 |
| Discover Peoria Getaway (ARV: $728) | Adolfo Matus | 10/28/2021 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Pat Dennehey | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Donna Draeger | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Carol Hohlen | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Susan Ilich | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Richard Miner | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Theresa Pretzer | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Heidi Renteria | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Kathy Riley | 4/11/2022 |
| Dean’s Night Out: 2x tickets to Rock of Ages at Paramount | Yvette Herczeg | 4/11/2022 |
| Air Supply at Four Winds Casino New Buffalo | Frank Longo | 4/18/2022 |
| Streets of Lake Geneva Fashion Week Hotel Giveaway | Shannon May | 4/22/2022 |
| Experience Jackson – Race Weekend Getaway ($525 value) | Susan Walker | 5/16/2022 |
| NV5 Invitational: 2x tickets to The Hangar all-inclusive hospitality | Kelly Turner | 5/16/2022 |
| Johnny Mathis at Four Winds Casino | Carol Kellen | 5/23/2022 |
| Johnny Mathis at Four Winds Casino | Carol Barz | 5/23/2022 |
| Johnny Mathis at Four Winds Casino | Don Ryzewski | 5/23/2022 |
| Johnny Mathis at Four Winds Casino | Louis Karagiannes | 5/23/2022 |
| Why Wait To Renovate – $250 Builder Supply Outlet local prize | Arlene Wax | 5/24/2022 |
| Roof for a Hero – Roof up to $17,5000 by Rogers Roofing for a veteran | Robert Joiner | 5/24/2022 |
| Grand Rapids Getaway ($1,790 value) | Rebecca Herrera | 6/1/2022 |
| $500 Petoskey Area Lodging | Laura Tritschler | 6/6/2022 |
| Indiana Beach overnight and passes | Heidi Renteria | 6/10/2022 |
| Lou’s Bloomington Barn Vacation Getaway ($1,000 value) | Elaine Sofferman | 6/30/2022 |
| Night on the Town – Chicago Northwest | Nancy Zurawski | 7/7/2022 |
| It’s All Here: Concert, Dinner, Overnight in Rosemont | Steve Maraffino | 7/7/2022 |
| Unforgettable Forgottonia Macomb Getaway | Kent Renn | 7/14/2022 |
| $50 Restore Hyper Wellness gift certificate (#1) | Christine Lantz | 7/18/2022 |
| $50 Restore Hyper Wellness gift certificate (#2) | Lisa Schaedler | 7/25/2022 |
| Champaign-Urbana $500 Getaway | Sandy Rasmussen | 8/1/2022 |
| Shipshewana Weekend Getaway/LaGrange County Visitors Bureau | Corine Scoglio | 8/2/2022 |
| $50 Restore Hyper Wellness gift certificate (#3) | Molly Piech | 8/2/2022 |
| $50 Restore Hyper Wellness gift certificate (#4) | Lois Fowler | 8/8/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Rexine Sokolnik | 8/11/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Tremaine Hargon | 8/11/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Irene Maksym | 8/11/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Dan Cooney | 8/11/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Joan Nehls | 8/11/2022 |
| Tchaikovsky Spectacular at Ravinia – 4 Lawn Admission | Judy Brandhorst | 8/11/2022 |
| Restore Hyper Wellness – $380 grand prize | James Kelly | 8/16/2022 |
| Lake Geneva Cruise Line – 4 adult tour tickets + $200 Pier 290 | Judy Donash | 8/22/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Janet Pero | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre- Dreamgirls | Joan Murray | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Sandra Machaj | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Heidi Bolder | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Emily Ward | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Laurie Hickman | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Tina Lux | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Petra Hein-Peters | 9/6/2022 |
| Dean’s Night Out at Paramount Theatre – Dreamgirls | Mary Leahy | 9/6/2022 |
| Dena’s Night Out at Paramount Theatre – Dreamgirls | Barbara Watters | 9/6/2022 |
| Hocking Hills Adventure Getaway ($800 value) | Laura O’Connor | 9/12/2022 |
| Bloomington, Indiana Getaway ($644 value) | Kathy Duffy | 9/19/2022 |
| Home Away From Home: Blackhawks in Milwaukee | Catherine Adamczyk | 9/20/2022 |
| Home Away From Home: Blackhawks in Milwaukee | Diane Cooper | 9/20/2022 |
| Paul Anka Premium Ticket Giveaway | Gary Patula | 10/5/2022 |
| Behind-the-Scenes at Mecum Auctions | Bob Hines | 10/10/2022 |
| Behind-the-Scenes at Mecum Auctions | Craig Gray | 10/11/2022 |
| Two Ticket Tuesdays at Two (10/21 game) | Glenn Kozeluh | 10/11/2022 |
| Two day getaway in Northwest Illinois | Susan Ribordy | 10/17/2022 |
| Two Ticket Tuesdays at Two (10/27 game) | C.C. Kay | 10/18/2022 |
| Two Ticket Tuesdays at Two (10/30 game) | Kimberly Asta | 10/25/2022 |
| Two Ticket Tuesdays at Two (11/14 game) | Don Langland | 11/1/2022 |
| Year’s worth of Brew Pub Pizza (ARV: $750) | Henry Julkowski | 11/2/2022 |
| Two Ticket Tuesdays at Two (11/16 game) | Cheryl Pranz | 11/8/2022 |
| Stairlift for a veteran (ARV: up to $3,900) | Alex Aratri | 11/10/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Heidi Bolger | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Bridget Broucek | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Bonnie Eaton | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Mary Jeanne Fitzgerald | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Karen Kelly | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Bill Kurczodyna | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | David Sanders | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Dan Sheehan | 11/14/2022 |
| Dean’s Night Out at Paramount Theatre – The Sound of Music | Ed Okrei | 11/14/2022 |
| Two Ticket Tuesdays at Two (11/20 game) | Deanne Frieders | 11/15/2022 |
| Two Ticket Tuesdays at Two (11/27 game) | Ted Hathorn | 11/22/2022 |
| Two Ticket Tuesdays at Two (12/9 game) | Georgette Brokopp | 11/29/2022 |
| Two Ticket Tuesdays at Two (12/13 game) | Debbie Salazar | 12/6/2022 |
| Lake Geneva Santa Cruise for four + $200 Pier 290 | Joseph Sullivan | 12/9/2022 |
| Two Ticket Tuesdays at Two (12/18 game) | Rick Reder | 12/13/2022 |
| Subscription for two – Marriott Theatre 2023 season | Lori Balsamo | 12/19/2022 |
| Omaha Steaks Holiday Gift Package | Lori Shaffer | 12/20/2022 |
| Two Ticket Tuesdays at Two (12/23 game) | Jane Pierri | 12/20/2022 |
| Two Ticket Tuesdays at Two (1/3 game) | Judy Maitland | 12/27/2022 |
| Rhino Cart for you and a friend | Jennifer Sweetman | 12/29/2022 |
| Taste of Swiss-consin (ARV: $350) | Chiffvette Rice | 12/30/2022 |
| Two Ticket Tuesdays at Two (1/8 game) | Brad Upperman | 1/3/2023 |
| Toro – December Product Impulse Endeavor Inverter | Sissy Brenn | 1/6/2023 |
| Two Ticket Tuesdays at Two (1/14 game) | Linda Miller | 1/10/2023 |
| Two Ticket Tuesdays at Two (1/22 game) | John Undesser | 1/17/2023 |
| Two Ticket Tuesdays at Two (2/7 game) | Melissa Cook | 1/24/2023 |
| Two Ticket Tuesdays at Two (2/10 game) | Kelly Cote | 1/31/2023 |
| Toro – January Product Snow Blower (ARV: $699) | Kathy Timm | 2/3/2023 |
| Granite Peak Ski Getaway for Two (ARV: $595) | Roman Lys | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Kerri Albin | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Nancy Belda | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Laura Beringer | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Anna Bernecka | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Constance Ten Bruin | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Mark Elias | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Sara Kerkemeyer | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Paula Nessie | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | George Sine | 2/6/2023 |
| Dean’s Night Out at Paramount Theatre – Into the Woods | Cheryl Trojanowski | 2/6/2023 |
| Tix package to Wuthering Heights at Chicago Shakespeare Theater | Karen Meifert | 2/6/2023 |
| Two Ticket Tuesdays at Two (2/19 game) | Bob Grazian | 2/7/2023 |
| Snowriver Mountain Resort Ski Getaway (ARV: $595) | Jerry Bauer | 2/13/2023 |
| Two Ticket Tuesday at Two (2/21 game) | Peter Nosal | 2/14/2023 |
| Two Ticket Tuesday at Two (3/4 game) | Phil Partipilo | 2/21/2023 |
| Two Ticket Tuesday at Two (3/6 game) | Tyler Tobolt | 2/28/2023 |
| Toro – February Product of the Month (ARV: $299) | Lenore Capua | 3/1/2023 |
| Two Ticket Tuesday at Two (3/14 game) | Guy Schingoethe | 3/7/2023 |
| Two Ticket Tuesday at Two (3/26 game) | Jim Renick | 3/14/2023 |
| Two Ticket Tuesday at Two (3/30 game) | Jason Johnson | 3/21/2023 |
| Two Ticket Tuesday at Two (4/1 game) | Debbie Stevens | 3/28/2023 |
| Toro – March Product of the Month (ARV $299) | Mary Gerard | 4/3/2023 |
| Tickets to Wayne Newton + Tony Orlando | John Kaleta | 4/3/2023 |
| Tickets to Wayne Newton + Tony Orlando | Roberta Arends | 4/3/2023 |
| Tickets to Wayne Newton + Tony Orlando | Gail Albert | 4/3/2023 |
| Two Tickets Tuesday at Two (4/13 game) | VIkki Rushing | 4/4/2023 |
| Wayne Newton/Tony Orlando at Hard Rock Live | Roberta Arends | 4/5/2023 |
| Dean’s Night Out at Paramount – School of Rock | Dennis Balk | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Janice Hildebrand | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Sally Juiris | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Roger LaRoussa | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Julia Levy | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Justin Mascarenas | 4/17/2023 |
| Dean’s Night Out at Paramount – School of Rock | Vivian Miner | 4/17/2023 |
| Wayne Newton/Tony Orlando at Hard Rock Live | Steve Buss | 4/18/2023 |
| Toro – April Product of the Month (ARV: $729) | Katherine Faulkner | 5/1/2023 |
| Hocking Hills Luxury Cabin Getaway (ARV: $1,000) | Denise Schaller | 5/2/2023 |
| Pat Tomasulo at Egyptian Theatre | Larry Bajmakovich | 5/16/2023 |
| Bloomington Indiana Mother’s Day Getaway (ARV: $599) | Latasha Sandoval | 5/18/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Pat Pindelski | 5/22/203 |
| West Side Story at Lyric Opera (ARV: $400) | Tracy Dietschweiler | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Chiffvette Rice | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Janet Cavenagh | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Cathy Virga | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Andy Murashige | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | Dave Levy | 5/22/2023 |
| West Side Story at Lyric Opera (ARV: $400) | William Murray | 5/22/2023 |
| $300 Gift of Geneva (INLURO, Stockholm’s Restaurant & Brewery, RJA Design) | Carol Noa | 5/22/2023 |
| 2023 NTT INDYCAR SERIES Sonsio Grand Prix at Road America package (event tickets, camping, campsite – ARV: $540) | George Berger | 5/30/2023 |
| Toro – May Product of the Month (ARV: $4,799) | Dave Stailey | 6/6/2023 |
| Escape to Unforgettable Forgottonia (ARV: $1,130) | Mary Levato | 6/14/2023 |
| Omaha Steaks Father’s Day $99 Package | Ginny Cummings | 6/19/2023 |
| Drill Dock Giveaway (ARV: $34.95) | James Gleissner | 6/19/2023 |
| Drill Dock Giveaway (ARV: $34.95) | Joseph Souligne | 6/19/2023 |
| Rhino Cart (ARV: $159.95) | Keith Poppen | 6/19/2023 |
| Rhino Cart (ARV: $159.95) | Steve Domian | 6/19/2023 |
| Bloomington Indiana Dad’s Day Getaway (ARV: $790) | Robert Prah | 6/22/2023 |
| $450 Gift of Geneva (Liz & Kate Boutique, Love Theory Bridal, Anastazia Treasures for the Home, GIA MIA Geneva, Livia Italian Eatery, Ella’s Italian Pub) | Beth Prueter | 6/22/2023 |
| Visit Lake Geneva – Black Point Estate & Gardens Sunset Tour for 8 (ARV: $500) | Erin Flannigan-Davies | 6/26/2023 |
| Taste of Swiss-consin: Green County Getaway (ARV: $300) | Maureen Taylor | 7/1/2023 |
| Toro – June Product of the Month (ARV: $219.99) | Jennifer Kowalski | 7/5/2023 |
| Visit Kankakee County for Music & More (ARV: $406) | Lana O’Brien | 7/5/2023 |
| Riverboat Twilight Signature 2-Day Cruise for 2 (ARV: $933.74) | Mary DeLucca | 7/7/2023 |
| Starved Rock Country Adventure Package (ARV: $1,000) | Bob Kolososki | 7/10/2023 |
| Inside the Ropes at NV5 Invitational (ARV: $1,000) | Tracy Ito | 7/10/2023 |
| 2x tickets to Ravinia with the CSO | Larry Colvin | 7/10/2023 |
| $300 Gift of Geneva (Lash Dash, The Herrington Inn & Spa, Atwater’s Restaurant, Pug & Hound Pet Apothecary) | Lauren Caliri | 7/25/2023 |
| Toro – July Product of the Month (ARV: $229.99) | Gail Albert | 8/1/2023 |
| Tickets to Kenny Loggins at Ravinia | Judy Button | 8/8/2023 |
| $550 Gift of Geneva (Crystal Life Technology, FoxFire Steakhouse, State Street Jewelers, Urban Artisan | Margaret Pearce | 8/22/2023 |
| $1,000 Wild Fork gift card | Lori Selof | 8/31/2023 |
| Toro – August Product of the Month (ARV: $299.99) | Davis Rann | 9/1/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Pat Totman | 9/5/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Joanne Gard | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Cynthia Kaminski | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Rebecca Gamboa | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Diane Goodman | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Nancy Farrell | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Diane Schmit | 9/6/2023 |
| Dean’s Night Out at Paramount – Little Shop of Horrors | Lori Balsamo | 9/6/2023 |
| Southwest Michigan Getaway (ARV: $500) | Pam Berger | 9/14/2023 |
| Hocking Hills Getaway (ARV: $1,280) | Dan Perrone | 9/22/2023 |
| $200 Gift of Geneva (Country Naturals, Little Barn Baby, Rookies Pub & Grill) | Matt Polovin | 9/25/2023 |
| Visit Lake Geneva September Getaway with Grand Geneva Resort (ARV: $1,401.37) | Christos Panos | 10/2/2023 |
| Toro – September Product of the Month (ARV: $299.99) | Sharon Uhlemann | 10/3/2023 |
| $300 Gift of Geneva (Little Red Barn Door, The Little Traveler, Craft Urban Restaurant) | Jennifer Boehm | 10/25/2023 |
| Toro – October Product of the Month (ARV: $199.99) | Angel Wendt | 11/1/2023 |
| Autumn Adventure in Janesville (ARV: $300) | Jim Harvey | 11/3/2023 |
| Visit Lake Geneva October Getaway with The Abbey Resort (ARV: $1892.62) | Mike McKeown | 11/7/2023 |
| Tickets to Locavore Farm’s Friendsgiving Feast & Overnight in Kankakee County (ARV: $430) | Vanessa Calderon | 11/8/2023 |
| Brew Pub Lotzza Motzza Pizza for a Year (ARV: $750) | Susan Alberts | 11/10/2023 |
| Dean’s Night Out at Paramount – Charlie | Helen Bacza | 11/14/2023 |
| Dean’s Night Out at Paramount – Charlie | Christine Callison | 11/14/2023 |
| Dean’s Night Out at Paramount – Charlie | Nancy Zurawski | 11/14/2023 |
| Dean’s Night Out at Paramount – Charlie | Roger Zellers | 11/14/2023 |
| Dean’s Night Out at Paramount – Charlie | Joan Mastin | 11/14/2023 |
| Dean’s Night Out at Paramount – Charlie | Mary Jeanne Fitzgerald | 11/14/2023 |
Winners are ineligible to win any other WGN(AM) contest or sweepstakes only once (1) every sixty (60) days. Only one (1) winner per household is permitted in any contest or sweepstakes. Winners are eligible to win a prize valued at $600 or more only once (1) every two (2) years.
