Chicago Sweepstakes
Found 18 total
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 Ken in Chicago Brazilian Lymph Spa 70 Minute Massage Giveaway.
One winner receives a 70-minute Body Detox Lymphatic Drainage Massage at Brazilian Lymph Spa Chicago (valued at $650).
In-person prize at Brazilian Lymph Spa in Chicago Illinois; winner must be able to visit the spa.
To enter, like the giveaway post, follow @brazilianlymphspa and @keninchicago on Instagram and tag a friend in the comments. More comments earn more entries.
Win $650 in value – Ken in Chicago Brazilian Lymph Spa 70 Minute Massage Giveaway - Enter Now
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 MegMade Interior Design Giveaway.
One winner gets a one-hour design consultation with the MegMade team (in home in the Chicago area or virtual elsewhere) plus a $500 MegMade gift card.
To enter, follow @megmade on Instagram, like the post and tag friends in the comments (tag as many as you like). Entries close November 10 2026 at 11:59 PM CST. Winner announced November 11.
Win $500 in value – MegMade Interior Design Giveaway - Enter Now
Art Deco Nutcracker Experience Giveaway offers tickets to the full Art Deco Nutcracker Ballet performance and a one‑night hotel stay in a King Room at Sofitel Chicago Magnificent Mile. - Tickets to the full Art Deco Nutcracker Ballet performance. - One‑night hotel stay in a King Room at Sofitel Chicago Magnificent Mile. The estimated retail value of the prize package is $650. The sweepstakes ends on November 11, 2026 at 11:59 PM CST.
To enter, follow @sofitelchicago, @aaballetcenterfordance, and @theathenaeum_chicago, like the post, and tag who you'd bring along (each comment counts as one entry).
Win $650 in value – Art Deco Nutcracker Experience Giveaway - 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 Fairmont Chicago The Ultimate Chicago Holiday Getaway Giveaway.
Fairmont Chicago The Ultimate Chicago Holiday Getaway Giveaway offers a single winner a holiday package. - 5 VIP viewing stand tickets to the Wintrust Magnificent Mile Lights Festival® on November 21, providing a front‑row view of the festivities, fireworks, festive surprises and holiday gifts. Total value $1,500.
No eligibility stated. Ends November 11, 2026 11:59 PM EST.
To enter, follow @fairmontchicago and @themagmile, like the post and comment on the post. The winner is picked after the giveaway ends.
Win $1,500 in value – Fairmont Chicago The Ultimate Chicago Holiday Getaway 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
