Pittsburgh Insider's Guide Sweepstakes 2026
Experience Pittsburgh in Every Season
Four Seasons. Four Winners. One Ultimate Trip.
To celebrate the launch of our 2026 Insider’s Guide, VisitPITTSBURGH is giving away four incredible 4-day / 3-night trips. Whether you want to see the city in full bloom or catch the winter magic, you choose when to visit.
Four winners will be selected for a 4-day / 3-night trip, with the flexibility to choose exactly when you want to visit.
The Prize Package
Four lucky winners will receive a curated Pittsburgh experience
- Hotel Stay: A 4-day / 3-night stay in the city.
- Airfare: Roundtrip flights for two.
- Experiences: A pair of tickets to a local attraction or experience.
- $500 Cash: A Visa Gift Card to fuel your exploration.
Ready to Go? How to Enter:
Entries are open from January 20–29, 2026. Follow these steps to get your name in the hat:
- Follow: Find us @VisitPITTSBURGH on Instagram or Facebook.
- Comment: Tag us with “ENTER” on the official sweepstakes post.
- Submit: Watch your DMs for a link to the official entry form. Note: You must complete the online form to qualify.
The Fine Print
- Entry Deadline: Submissions close January 29, 2026.
- Winner Selection: Four random winners will be notified via DM on January 29.
- Travel Window: You must complete your travel by December 31, 2026. Hotel blackout days apply.
- No purchase necessary. Terms and conditions apply.
- We will NOT ask you for your credit card information to claim your prize.
- This giveaway is not affiliated or associated with Instagram or Facebook.
