$80 Cheap flight deals from Chicago (CHI) to Windsor (HFD)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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
Orbitz is the best place to find guaranteed low prices on Chicago to Windsor flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.
Find Cheap Chicago to Windsor Flights
Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to Windsor. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.
Get Miles and Points for Your Flight
Simply enter your frequent flyer information while booking to get miles or points for qualifying Chicago to Windsor flights. This information can all be saved in your Orbitz account, which means it will not have to be entered each time you take advantage of a great air fare deal.
Flight Alerts Take Away the Stress
Orbitz does not want travelers to worry on their flights from Chicago to Windsor. We keep you updated on any flight changes for Chicago to Windsor flights with alerts sent directly to your email or a mobile device. These alerts can also be sent to friends and family.
Discount Travel Planning Made Simple
You will have no problems finding budget flights from Chicago to Windsor on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.
Flights from Chicago
- Chicago to Los Angeles
- Chicago to New York
- Chicago to Orlando
- Chicago to Toronto
- Chicago to Houston
- Chicago to London
- Chicago to Detroit
- Chicago to Phoenix
- Chicago to Rome
- Chicago to Cleveland
- Chicago to Dallas
- Chicago to New Orleans
- Chicago to San Francisco
- Chicago to Washington
- Chicago to Paris
- Chicago to Sao Paulo
- Chicago to Sacramento
- Chicago to Killeen
- Chicago to Kansas City
- Chicago to Montreal
Windsor Airports
More Destinations
- Flights from Chicago to East Windsor
- Flights from Raleigh to East Windsor
- Flights from Newark to East Windsor
- Flights from Alexandria (AEX) to Hartford (BDL)
- Flights from Bar Harbor (BHB) to Hartford (BDL)
- Flights from Dalian (DLC) to Hartford (BDL)
- Flights from Houston (EFD) to Hartford (BDL)
- Flights from Frankfurt (FRA) to Hartford (BDL)
- Flights from Hagerstown (HGR) to Hartford (BDL)
- Flights from Indianapolis (IND) to Hartford (BDL)
- Flights from Lafayette (LAF) to Hartford (BDL)
- Flights from La Crosse (LSE) to Hartford (BDL)
- Flights from Modesto (MOD) to Hartford (BDL)
- Flights from Page (PGA) to Hartford (BDL)
- Flights from Perpignan (PGF) to Hartford (BDL)
- Flights from Peoria (PIA) to Hartford (BDL)
- Flights from Santiago (STI) to Hartford (BDL)
- Flights from Tallahassee (TLH) to Hartford (BDL)
- Flights from Dothan to Windsor Locks
- Flights from Okinawa Island to Windsor Locks
- Flights from Bergerac to Windsor Locks
- Flights from Hefei to Windsor Locks
- Flights from Madurai to Windsor Locks
- Flights from Atlanta to Windsor Locks
- Flights from Boston to Windsor Locks
- Flights from Charlotte to Windsor Locks
- Flights from Chicago to Windsor Locks
- Flights from Dallas to Windsor Locks
- Flights from Denver to Windsor Locks
- Flights from Detroit to Windsor Locks
- Flights from Dublin to Windsor Locks
- Flights from Ho Chi Minh City to Windsor Locks
- Flights from Kansas City to Windsor Locks
- Flights from Los Angeles to Windsor Locks
- Flights from Minneapolis - St. Paul to Windsor Locks
- Flights from Nashville to Windsor Locks
- Flights from New Orleans to Windsor Locks
- Flights from New York to Windsor Locks
- Flights from Orlando to Windsor Locks
- Flights from Philadelphia to Windsor Locks
- Flights from Phoenix to Windsor Locks
- Flights from Raleigh to Windsor Locks
- Flights from Seattle to Windsor Locks
- Flights from Vienna to Windsor Locks
- Flights from Washington to Windsor Locks
- Flights from Nice to Windsor Locks
- Flights from Karachi to Windsor Locks
- Flights from Melbourne to Windsor Locks
- Flights from Marudi to Windsor Locks
- Flights from Nalchik to Windsor Locks
- Flights from Blountville to Windsor Locks
- Flights from San Pedro Sula to Windsor Locks
- Flights from Moncton to Windsor Locks
- Flights from Arequipa to Windsor Locks
- Flights from Abbotsford to Windsor Locks
- Flights from Ordu to Windsor Locks
- Flights from Kalamazoo to Windsor Locks
- Flights from Tamworth to Windsor Locks
- Flights from Myrtle Beach to Windsor Locks
- Flights from Fort Lauderdale to Windsor Locks
- Flights from Santa Barbara to Windsor Locks
- Flights from Worcester to Windsor Locks
- Flights from Vero Beach to Windsor Locks
- Flights from Fort Myers to Windsor Locks
- Flights from Eugene to Windsor Locks
- Flights from Spokane to Windsor Locks
- Flights from Rochester to Windsor Locks
- Flights from Greensboro to Windsor Locks
- Flights from Dayton to Windsor Locks
- Flights from Tucson to Windsor Locks
- Flights from Tampa to Windsor Locks
- Flights from Augusta to Windsor Locks
- Flights from Gainesville to Windsor Locks
- Flights from Hannover to Windsor Locks
- Flights from Carcassonne to Windsor Locks
- Flights from Guatemala City to Windsor Locks
- Flights from Olympia to Windsor Locks
- Flights from Mahikeng to Windsor Locks
- Flights from Newport News to Windsor Locks
- Flights from Potosi to Windsor Locks
- Flights from Obihiro to Windsor Locks
- Flights from Meridian to Windsor Locks
- Flights from Malappuram to Windsor Locks
- Flights from Louisville to Windsor Locks
- Flights from St. Thomas to Windsor Locks
- Flights from Barreiras to Windsor Locks
- Flights from Sidoarjo to Windsor Locks
- Flights from Puerto Asis to Windsor Locks
- Flights from Valbo to Windsor Locks
- Flights from Edmonton International Airport to Windsor Locks
- Flights from Lower Bogue to Windsor Locks
- Flights from Huanchaco to Windsor Locks
- Flights from Craiova to Windsor Locks
- Flights from Aguadilla to Windsor Locks
- Flights from South Burlington to Windsor Locks
- Flights from Whitsundays to Windsor Locks
- Flights from Columbia to Windsor Locks
- Flights from Gravenhurst to Windsor Locks
- Flights from Chipata to Windsor Locks
- Flights from Palenque to Windsor Locks
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.