$112 Cheap flight deals from Chicago (CHI) to Windsor (HFD)
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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 $112 One Way, $204 Round Trip from Chicago to Windsor
Prices starting at $204 for return flights and $112 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
Pier Blue Inn Old Saybrook - Essex
Jul 8 - Jul 11
Chicago (CHI) to New Haven (HVN)
New Haven (HVN) to Chicago (CHI)
Reviewed on Mar 20, 2026
Saybrook Point Resort & Marina
Jul 8 - Jul 11
Chicago (CHI) to New Haven (HVN)
New Haven (HVN) to Chicago (CHI)
Reviewed on Dec 19, 2022
More About Flying To Windsor from Chicago
Route Information for Flights from Chicago to Windsor
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | HFD |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Windsor
Orbitz assures that you will receive cheap air fares on flights from Chicago to Windsor and special deals that give you guaranteed low prices on hotels, cruises, car rentals, and anything else you need on your trip.
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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.