$257 Cheap flight deals from Windsor (YQG) to Chicago (CHI)

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Airfares from $257 One Way, Round Trip from Windsor to Chicago

Prices starting at for return flights and $257 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Chicago from Windsor

Route Information for Flights from Windsor to Chicago

Origin Airport IATA Code
YQG
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Windsor to Chicago

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Family Matters, and So Do Cheap Tickets

Don’t miss another birthday, graduation or wedding, wherever they are. Take advantage of Orbitz On-the-Go’s discount travel planning features to save on flights from Windsor to Chicago and Windsor to Chicago flights. Tell them you’ll be there, every single time.

Escape to Romance

Treat yourself and the one you love to a romantic hideaway. Orbitz budget air flights from Windsor to Chicago and Windsor to Chicago flights can be bundled into packages for extravagant savings at spa resorts and hotels.

See the World

It’s finally your time. Go wherever the wind takes you. Orbitz On-the-Go makes dreams come true. Book low fare flights from Windsor to Chicago, the world is at your fingertips.

Flight or Gate Changes? No Problem

Once you’ve reserved your low cost air ticket on Windsor to Chicago flights or flights from Windsor to Chicago, stay informed with Orbitz On-the-Go free alerts. Choose from email, voice and text notification. You’ll always know your flight status and gate number, and where and how to pick up your bags.

Frequently asked questions

What is the shortest flight from Windsor to Chicago?
If the weather is good and there are no delays, you could be jetting into ORD from Windsor Intl. Airport in just 2 hours and 53 minutes. With such a short flight time, consider traveling with carry-on luggage only.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.