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Lowest round trip fares by airline from Chicago and Windsor
Cheapest prices ($59 One Way, $163 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Great Deals On Cheap Hotels in Windsor
Hampton Inn & Suites Windsor - Sonoma Wine Country
Reviewed on May 5, 2024
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
Reviewed on May 8, 2024
WorldMark Windsor
Reviewed on Apr 24, 2024
Fly From Chicago to Windsor
Origin | Chicago |
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Destination | Windsor |
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Cheap flights from Chicago to Windsor
Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.
If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.
Save Even More Time and Money With a Windsor Travel Package
Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Windsor vacation that you can't get when you book flights and hotel separately.
Relax in Windsor With Confidence and Convenience
Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.
Need to grab a cheap travel deal while you're on the go? Download our mobile app, where you can search and book just like you would on your home computer. Stay in-the-know on great rates on flights from Chicago to Windsor by signing up for exclusive email deals.