Chicago Sweepstakes
Found 17 total
Enter to win the City Credit Union Joy All Around Sweepstakes - 6 Winners.
Six winners: one Grand Prize is a four-night trip for two to New York City, Los Angeles, Miami or Chicago, including round-trip air, ground transportation, hotel accommodations and a $250 Mastercard Prepaid card (ARV $5500); two First Prizes of a $500 Mastercard Prepaid card each; and three Second Prizes of a $250 Mastercard Prepaid card each. Total ARV $7250.
Open to legal residents of the 50 US and DC who have reached the age of majority in their state (19+ in AL and NE, 21+ in MS), excluding Florida, New York and Rhode Island. Ends January 31 2027 at 11:59 PM CT.
To enter, use a City Credit Union Mastercard debit card for eligible signature-based purchases (one entry per purchase), or send a free email AMOE with your full name, complete mailing address, telephone number, date of birth and email address to [email protected] with the subject line City Credit Union Joy All Around Sweepstakes (one AMOE entry per email). Limit 400 entries per person during the promotion period, regardless of method.
Win $7,250 in value – City Credit Union Joy All Around Sweepstakes - 6 Winners - Enter Now
Enter to win the Cumulus Twisted 2026 Flyaway Contest.
One winner gets a trip for 2 to all 3 nights of the Twisted 2026 concert series in Chicago (December 8-10, 2026) with round-trip airfare and 3 nights hotel. ARV $3000.
Open to legal U.S. residents 21 or older with a valid Social Security number who live within 100 miles of a participating Cumulus station (Appleton WI, Atlanta, Buffalo, Cincinnati, Columbus/Starkville MS, Eugene, Fayetteville AR, Grand Rapids, Indianapolis, Memphis, Minneapolis, New Orleans, Oklahoma City, Peoria, Saginaw, Salt Lake City, Syracuse and Youngstown markets).
To enter, listen to a participating station on weekdays for the 4 daily Secret Keywords (6-9 AM, 9-noon, noon-3 PM and 3-7 PM local time) and text each one to 95819 by 11:59 PM ET that day, or submit the keywords free on the no-purchase entry form at https://amoe.textgroove.com/8900ea64-622f-438a-8620-bb6d61260162 (up to 4 entries per day). One nationwide drawing about November 23, 2026. Ends November 20, 2026.
Win $3,000 in value – Cumulus Twisted 2026 Flyaway Contest - Enter Now
Enter to win the Layla Chicago Pout Perfection Giveaway.
One winner receives a complimentary Juvederm lip filler treatment with Layla at JEM Medspa in Elmhurst IL.
Open to residents of Illinois and Indiana 21+ who can travel to Elmhurst; consultation required. Ends November 15, 2026 at 11:59 PM CST.
To enter, like the post, follow @jemmedspa and @laylatheinjector on Instagram and TikTok and tag 2 friends. Share to your story and tag both for a bonus entry.
Win $650 in value – Layla Chicago Pout Perfection Giveaway - Enter Now
Enter to win the The Shops at North Bridge and The Gwen Chicago Holiday Getaway Giveaway.
One winner receives a $500 shopping spree at The Shops at North Bridge, a $100 food and beverage gift card to Upstairs at the Gwen and a one-night stay at The Gwen Chicago. All prizes must be redeemed during Holiday Shopping Week, December 4-18 2026, and the prize must be picked up at The Shops at North Bridge.
Open only to legal US residents residing in Illinois, age 18 or older. No purchase necessary. Ends November 16 2026 at 11:59 PM CST.
To enter, follow @theshopsatnorthbridge and @thegwenchicago, like the Instagram post and tag a friend in the comments (each tag is an additional entry). The winner is announced in the comments on November 17 and contacted by DM from @theshopsatnorthbridge only.
Enter to win the Arm & Hammer Biggest Jingle Ball Ticket Giveaway - 25 Winners Per City.
Twenty-five winners in each of 9 cities receive a pair of tickets (airfare and hotel are not included) to that city's iHeartRadio Jingle Ball 2026: Dallas/Fort Worth at Dickies Arena on December 1; Los Angeles at Intuit Dome on December 4; Chicago at Allstate Arena on December 7; Detroit at Little Caesars Arena on December 8; New York at Madison Square Garden on December 11 (ARV $320 per prize); Boston at TD Garden on December 13; Washington DC at Capital One Arena on December 14; Philadelphia at Xfinity Mobile Arena on December 15; and Nashville at Bridgestone Arena on December 17. ARV is $200 per prize in the other cities ($48000 total).
Open to 18+ (or age of majority) legal residents of the 50 United States and DC.
To enter, visit iheartradio.com/AHBigWin, select a city, and complete the official entry form; limit 1 entry per person/email/household per day through November 18, 2026 at 11:59 PM ET.
Enter to win the Orlando Magic Sports Fan Getaway Sweepstakes.
One winner receives four tickets to the winner's choice of an Orlando Magic away game (San Antonio Spurs on February 4 2027, Chicago Bulls on March 15 2027, or Miami Heat on April 11 2027), four round-trip airline tickets to that city, and hotel accommodations (one quad room) for three nights for four people. Approximate retail value $4,450 to $4,950 (listed at $4,950).
Open to legal residents of Florida age 18 or older who live within 150 miles of Orlando and not within 75 miles of Miami, and who are eligible to lawfully attend events at the Kia Center. Ends December 28 2026 at 11:59 PM ET. Drawing on January 4 2027.
To enter, complete the official online entry form at the Qualtrics link and click submit (limit one entry per person). No purchase necessary.
Win $4,950 in value – Orlando Magic Sports Fan Getaway Sweepstakes - Enter Now
Enter to win the GOLFZON Miami Dolphins Sweepstakes.
One grand prize winner receives a Miami Dolphins VIP package: four tickets to the Dolphins vs. Chicago Bears game on December 13, 2026 at Hard Rock Stadium, a signed player jersey, a field pass and a tunnel pass, and a round of GOLFZON virtual golf with a Dolphins player (ARV $3,410).
Only open to Florida residents 18 and older; no purchase necessary. Ends December 5, 2026 (listed 11:59 PM PST); winner drawn on or around December 6.
To enter, complete the entry form on the GOLFZON Miami Dolphins Sweepstakes page; limit one entry per person.
Win $3,410 in value – GOLFZON Miami Dolphins Sweepstakes - Enter Now
Enter to win the Do312 Adler Planetarium Chicago Staycation Giveaway.
One winner gets 2 Adler Planetarium museum and Dome Show tickets, Adler merch, a 1-night stay at Hotel Lincoln and a 1-year DoMORE membership. No value is stated; estimated about $400.
No eligibility is stated; the prize is in Chicago IL. Ends 11-15-2026 6:00 PM CST.
To enter, fill out the giveaway form on the do312.com Adler Planetarium Staycation page (linked from @do312's bio). Winner chosen after November 15, 2026.
Win $400 in value – Do312 Adler Planetarium Chicago Staycation Giveaway - Enter Now
Enter to win the Throwback 100.3 Backstreet Boys at Sphere NYE Sweepstakes.
Prize: 2 tickets to the Backstreet Boys at Sphere in Las Vegas on December 31, 2026, round-trip airfare for 2 from Chicago ORD and 2 hotel nights (ARV $2500, 1 winner).
Open to residents 21+ of the Chicago-area counties in IL, Kenosha County WI and Lake and Porter counties IN. Runs November 2 - November 27, 2026 at 11:59 PM CT.
To enter, listen to Throwback 100.3 WTBC for the code word announced 5 times a day and submit it in the station stream player or app during that daily entry period.
Win $2,500 in value – Throwback 100.3 Backstreet Boys at Sphere NYE Sweepstakes - Enter Now
Enter to win the Chicago Bears Dr Pepper Ultimate Gameday Experience Sweepstakes.
One winner gets four tickets to the Bears vs Lions game on January 3, 2027 at Soldier Field, four pre-game sideline passes, $200 in Soldier Field concessions balance, one parking pass, one Chicago Bears autographed item, a 15-minute alumni meet and greet, a $500 Chicago Bears Pro Shop gift card and four knit hats; ARV $8688.
Open to contiguous US residents 18+ except Florida, New York and Rhode Island. Ends December 4, 2026 at 11:59 PM CST.
To enter, complete the online entry form at chicagobears.com/sweepstakes/drpepper with your name, date of birth, email, state and phone number; limit one entry per person. The winner is drawn on or about December 7, 2026.
Win $8,688 in value – Chicago Bears Dr Pepper Ultimate Gameday Experience Sweepstakes - Enter Now
