Big signs.
Bigger impact.
The largest Chicago-based independent sign company in the market, with 60 sign faces, almost all on Chicago-area expressways.
Book a free consultation- 60
- sign faces across the Chicago market
- Expressways
- where almost every Windsor sign stands
- Mid-1990s
- first two signs built, across the street from O'Hare
Your message, placed where Chicago travels
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Expressway Billboards
Large-format sign faces on Chicago-area expressways, placed where daily commuters and travelers pass every day.
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Location Planning
Tell us who you need to reach. We help you choose the faces and the direction of travel that put your message in front of them.
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Flexible Campaigns
Run one sign or several, for a short push or a long stay. We shape the campaign around your goals and budget.
“We started with two signs across from O'Hare. The idea hasn't changed: put the message where people can't miss it.”Jim CaraherFounder
In the mid-1990s, Mr. Caraher started Windsor Outdoor as a diversification of his real estate investment business. He built his first two signs on the site of office buildings he owned across the street from O'Hare Airport in Chicago. He grew Windsor into the largest Chicago-based independent sign company in the market, with 60 sign faces, almost all on Chicago-area expressways.
Book a free consultation
| Monday – Friday | 9:00 am – 5:00 pm |
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| Saturday – Sunday | Closed |