$119 Cheap flight deals from Chicago (CHI) to Windsor (OAK)
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This Weekend's Flight Deals from Chicago to Windsor
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $119 One Way, $242 Round Trip from Chicago to Windsor
Prices starting at $242 for return flights and $119 for one-way flights to Windsor were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Windsor economy flight packages
DoubleTree by Hilton Hotel Berkeley Marina
Jan 27 - Jan 29
Chicago (MDW) to Oakland (OAK)
Reviewed on Nov 10, 2025
Homewood Suites by Hilton Oakland-Waterfront
Jan 27 - Jan 29
Chicago (MDW) to Oakland (OAK)
Reviewed on Dec 12, 2025
Holiday Inn Express Hotel & Suites Oakland-Airport by IHG
Jan 27 - Jan 29
Chicago (MDW) to Oakland (OAK)
Reviewed on Aug 6, 2025
More About Flying To Windsor from Chicago
Route Information for Flights from Chicago to Windsor
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | OAK |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Windsor
If you are looking to get guaranteed low prices for Chicago to Windsor flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.
Get Package Savings by Booking Flights and Hotels at the Same Time
Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Windsor if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.
Orbitz for Business Helps Corporations save Money
Orbitz can assist all businesses from the small to major corporations with discounts on flights from Chicago to Windsor. We fine- tune your needs for Chicago to Windsor flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.
Using Online Check-In Makes Flying Simple
You can use the Orbitz website to check-in for your flights from Chicago to Windsor. You can also make changes to your schedule or even cancel a flight.
Flights from Chicago
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Windsor Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.