$364+ Cheap flights from Chicago (CHI) to Windsor, ON (YQG)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQG
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Windsor with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Windsor
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to WindsorExplore the most affordable flight options available from Chicago to Windsor. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Chicago to Windsor. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This Mytrip deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:40 pm -
3 stops21h 11m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Multiple Airlines logo]()
$692
This Flightnetwork deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:20 pm -
2 stops29h 31m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/1![Multiple Airlines logo]()
$711
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
1 stop4h 55m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Air Canada logo]()
$715
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:50 pm -
1 stop4h 55m
Sun 11/1510:35 am -
1 stop6h 03m
Deal found 10/4![Air Canada logo]()
$730
This Flightnetwork deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:50 pm -
1 stop4h 55m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/1![Air Canada logo]()
$731
Best flights from Chicago to WindsorDiscover carefully curated flight deals from Chicago to Windsor that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Chicago to Windsor that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This Mytrip deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:40 pm -
3 stops21h 11m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Multiple Airlines logo]()
$692
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
1 stop4h 55m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Air Canada logo]()
$715
This Flightnetwork deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:20 pm -
2 stops29h 31m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/1![Multiple Airlines logo]()
$711
This Air Canada deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:05 am -
2 stops10h 40m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/2![Air Canada logo]()
$739
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am -
2 stops10h 40m
Sun 11/1510:35 am -
1 stop6h 03m
Deal found 10/4![Air Canada logo]()
$739
This Air Canada deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:50 pm -
1 stop4h 55m
Mon 11/2310:35 am -
1 stop6h 13m
Deal found 10/2![Air Canada logo]()
$771
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2512:50 pm -
1 stop4h 55m
Sat 2/2710:35 am -
1 stop6h 03m
Deal found 10/4![Air Canada logo]()
$889
Last-minute flights from Chicago to WindsorDiscover last-minute flight deals from Chicago to Windsor. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Windsor. Data last updated October 5, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:50 pm -
1 stop4h 55m
Sun 11/1510:35 am -
1 stop6h 03m
Deal found 10/4![Air Canada logo]()
$730
This Flightnetwork deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:20 pm -
2 stops29h 31m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/1![Multiple Airlines logo]()
$711
This Flightnetwork deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:50 pm -
1 stop4h 55m
Sun 11/2210:35 am -
1 stop6h 03m
Deal found 10/1![Air Canada logo]()
$731
This Mytrip deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:40 pm -
3 stops21h 11m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Multiple Airlines logo]()
$692
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
1 stop4h 55m
Tue 11/2410:35 am -
2 stops10h 17m
Deal found 10/3![Air Canada logo]()
$715
One-way flights from Chicago to WindsorSearch for one-way flight options from Chicago to Windsor. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Chicago to Windsor. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:50 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$364
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:45 am -
2 stops8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$416
This Air Canada deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:45 am -
2 stops8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:15 am -
3 stops34h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$439
This Porter Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:20 pm -
2 stops23h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Porter Airlines logo]()
$486
This KAYAK deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:20 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$522
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:40 pm -
1 stop11h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
3 stops21h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
3 stops54h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$549
Find flight deals from Chicago to Windsor
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Windsor (YQG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $692 (Mytrip) |
One-way from | $364 (Air Canada) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Windsor that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
Use the filters below to find and compare flights from Chicago to Windsor that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Wed 10/28
12:50 pm-6:45 pm
1 stop4h 55m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$364
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Thu 10/15
8:40 pm-9:22 am
1 stop11h 42m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$441
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Thu 11/5
6:20 pm-6:51 pm
2 stops23h 31m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$486
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Fri 10/23
9:20 pm-9:22 am
1 stop11h 02m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$522
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Mon 10/12
8:40 pm-9:22 am
1 stop11h 42m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$540
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Thu 10/15
5:30 pm-3:46 pm
3 stops21h 16m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$543
Quickest round-trip
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Wed 10/14
12:59 pm-6:42 pm
1 stop4h 43m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$551
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Sun 10/11
12:59 pm-6:42 pm
1 stop4h 43m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$629
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Tue 10/13
7:11 am-6:42 pm
2 stops10h 31m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$635
ChicagoWindsor
ORD Chicago O'Hare Intl - YQG Windsor
ORDYQG
Chicago O'Hare Intl
Sat 10/10
5:00 am-6:42 pm
2 stops12h 42m
Windsor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$681
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Chicago to Windsor
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Windsor in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Windsor, Ontario flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Windsor, Ontario flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Windsor, Ontario flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Windsor, Ontario flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Windsor, Ontario flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Windsor
Have a flexible travel schedule? Discover the best time to fly to Windsor from Chicago with our price prediction graph.
CHI-YQG
ORD-YQG
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Windsor
CHI-YQG
ORD-YQG
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Windsor. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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