$103 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 $103 One Way, $208 Round Trip from Chicago to Windsor
Prices starting at $208 for return flights and $103 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
Landing Apartments New Haven Near Dixwell
Oct 8 - Oct 12
Chicago (ORD) to New Haven (HVN)
Reviewed on May 25, 2026
Windsor first class flight packages
Trumbull Marriott Shelton
Sep 17 - Sep 20
Chicago (CHI) to New Haven (HVN)
Reviewed on Aug 13, 2026
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
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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.