Route 66 Byway, Illinois Photo Contest
Travel along Route 66 between Chicago and St. Louis during the month of August 2025, and take photos of 20 or more of the designated places along the way to win your share of $3,000!
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Use the QR code to enter the contest
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How it works
1
Get the Overlook mobile app to access the Route 66 Byway, Illinois itinerary
2
Travel along the byway and visit 20 or more of the designated places
3
Take and upload photos to enter them into the contest
Winners will be announced in September
Travelers can compete for first, second, and third place in three categories:
“20-or-more”, “30-or-more”, or “All-40”, with prizes and glory for all the winners!
By continuing, you agree to our contest Terms and Conditions
Frequently asked questions
How does it work?
Drive along Route 66 between Chicago and St. Louis during the month of August 2025, and visit 20 or more of the 40 designated special places along the way. At each place, use the app to upload at least one beautiful photo to mark your visit.
How do I submit my photo?
Once you've arrived at the designated place, use the Overlook app to confirm your visit and upload your photo by clicking the image upload button or clicking into the place and marking as Visited.
What are the prizes?
The grand prize will be $500, with other categories and prizes to be announced soon!
When does it start and end?
The contest runs August 1, 2025 to August 31, 2025. You must visit in August 2025!
How many photos can I submit?
Submit between one and five photos for at least 20 designated places along the route to be eligible for prizes.
When will winners be announced?
Winners will be announced and notified in September.
How can I get help or report an issue?
Email support@overlookmaps.com and we will be happy to help.
Join the Route 66 Byway, Illinois Photo Contest
Use the QR code to get the Overlook app and enter the contest