$80 Cheap flight deals from Chicago (CHI) to Winchester (CHA)
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This Weekend's Flight Deals from Chicago to Winchester
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 $80 One Way, $148 Round Trip from Chicago to Winchester
Prices starting at $148 for return flights and $80 for one-way flights to Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Winchester economy flight packages
Bluegreen Downtown Nashville
Apr 12 - Apr 14
Chicago (ORD) to Nashville (BNA)
Reviewed on Jul 13, 2025
Conrad Nashville
Apr 14 - Apr 17
Chicago (ORD) to Nashville (BNA)
Nashville (BNA) to Chicago (ORD)
Reviewed on Oct 8, 2025
More About Flying To Winchester from Chicago
Route Information for Flights from Chicago to Winchester
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | CHA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Winchester
It has never been easier to find cheap Chicago to Winchester flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
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Get the Best Deals on Chicago to Winchester Flights
Finding great deals on flights from Chicago to Winchester is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Winchester vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Winchester flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.
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Stay on top of the latest updates for flights from Chicago to Winchester. We send you free email and mobile alerts to keep you informed about delays to Chicago to Winchester flights.
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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.