City Spotlight: Best Ongoing Sweepstakes in Chicago
Chicago is a city of big wins and bigger energy—from neighborhood street fests to sold-out games at the United Center. If you love no-purchase-necessary prizes that pop up again and again, here’s a practical guide to the best ongoing or frequently recurring sweepstakes Chicagoans can tap into, plus tips to play smarter and stay safe.
Top picks for ongoing or frequently recurring sweepstakes
1) ZipSweep (Daily, free, citywide)
ZipSweep is a free, ad-funded daily sweepstakes built around U.S. ZIP codes—including every Chicago ZIP. Each day, a winning code (ZIP + unique user ID) is randomly generated. If the exact winner claims by 9 PM, the prize is theirs. If not, we sometimes roll the prize over to the entire ZIP code—first come, first served—at our discretion. It’s fast, fair, and frictionless: no tickets, no payments, no catch. We only use your email for daily reminders and occasional updates, and we’ll never share your details unless you say it’s OK. ZipSweep is a free sweepstakes, not a lottery or gambling.
2) Chicago sports teams and arenas
Pro and semi-pro teams in Chicago often run recurring giveaways for tickets, merch, and VIP experiences. Keep an eye on:
- Basketball & Hockey at the United Center (Chicago Bulls, Chicago Blackhawks)
- Baseball (Chicago Cubs, Chicago White Sox)
- Football and Soccer (Chicago Bears, Chicago Fire FC)
- WNBA (Chicago Sky)
Tip: Subscribe to team newsletters and follow official social accounts; many promos run seasonally but recur year after year.
3) Chicago radio stations
Local stations frequently host keyword draws, ticket drops, and flyaway sweepstakes. Popular ones include Top 40, adult contemporary, and sports talk stations in the Chicago market. Watch their websites, morning shows, and social feeds for recurring campaigns.
4) Festivals and venues
Major annual events and venues often repeat giveaways each season, especially for ticket bundles and upgrades:
- Music festivals (e.g., large summer festivals, venue anniversaries)
- Iconic halls and theaters across the Loop, River North, and West Loop
- Neighborhood street fests (Lincoln Park, Wicker Park, Pilsen, Hyde Park)
Tip: Follow event calendars and local culture newsletters—many run monthly or seasonal contests.
5) Food and beverage brands
Chicago-loved eateries and beverage brands periodically run monthly or quarterly sweepstakes for gift cards, merch, or experiences. Sign up for email clubs and check promotional pages—these often recur.
6) Travel and experiences
Airlines with a big Chicago presence and local hospitality groups occasionally run ongoing or seasonal sweepstakes for flights, hotel stays, or staycations. These often return annually or quarterly.
7) Museums and attractions
Major institutions—think science, art, and aquarium staples—sometimes host recurring promotions tied to exhibits or membership drives. Keep an eye on newsletters and member pages for repeating patterns.
How to spot legit sweepstakes (and skip the spam)
- No purchase necessary: Real sweepstakes never require payment to enter or win.
- Official rules: Look for eligibility (age, residency), entry period, odds, prize details, and sponsor name/address.
- One entry vs. daily entry: Many allow daily entries—set reminders.
- Privacy: Reputable sponsors state how they use your data. For ZipSweep, we only use your email for reminders and occasional updates, and never share it unless you opt in.
- Taxes: In the U.S., prizes with ARV $600+ may be reported for tax purposes; plan accordingly.
A simple Chicago “win-more” routine
- Daily: Check ZipSweep and your email for claim windows; rollovers can make ZIP-wide grabs time-sensitive.
- Twice weekly: Scan team and venue newsletters for recurring promos.
- Weekly: Review radio station contest pages; many run ongoing cash or ticket giveaways.
- Monthly: Revisit festival, museum, and brand pages—many promos reset each month or quarter.
Final word
Chicago’s sweepstakes scene is lively and repeatable if you know where to look. Prioritize trustworthy, no-purchase-necessary promotions, keep a tight routine, and capitalize on daily opportunities like ZipSweep—especially if your ZIP sees a rollover. Always read official rules and eligibility, and good luck out there.