$80 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 $80 One Way, $159 Round Trip from Chicago to Windsor
Prices starting at $159 for return flights and $80 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
Comfort Inn Naugatuck-Shelton, CT
Apr 3 - Apr 6
Chicago (ORD) to New Haven (HVN)
Reviewed on Sep 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 | HFD |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Windsor
Great Deals on Flights From Chicago to Windsor
Spend more of your time and money at Windsor instead of sitting at your computer, searching for discount Chicago to Windsor flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Windsor.
Flights That Fit Your Budget
Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Windsor flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.
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Search for Flights from Chicago to Windsor on the Go
Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Windsor. Find cheap Chicago to Windsor flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.
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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.