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Cheap flights from Windsor, ON to Chicago from C$ 365

YQG — CHI
23 Oct — 30 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Chicago

Tue 20/1010:05 a.m. -
1 stop4h 18m
Tue 27/1012:50 p.m. -
1 stop4h 55m
Deal found 21/9C$ 683
Mon 26/1010:35 a.m. -
1 stop6h 03m
Wed 28/1012:50 p.m. -
1 stop4h 55m
Deal found 19/9C$ 684
Tue 3/1110:35 a.m. -
1 stop6h 03m
Tue 10/117:05 a.m. -
2 stops10h 40m
Deal found 18/9C$ 695
Sun 1/1110:35 a.m. -
1 stop6h 03m
Sun 8/117:05 a.m. -
2 stops10h 40m
Deal found 18/9C$ 729
Mon 26/107:00 a.m. -
2 stops11h 40m
Wed 28/106:20 p.m. -
3 stops23h 31m
Deal found 19/9C$ 853
Tue 6/107:25 p.m. -
1 stop13h 35m
Sat 10/109:20 p.m. -
1 stop11h 02m
Deal found 22/9C$ 874

Find flight deals from Windsor to Chicago

Round-trip from

C$ 683

One-way from

C$ 365
Air Canada
  • Air Canada
  • 20/10-27/10
  • 2 total stops
  • 9h 13m total
  • Windsor to Chicago
Search Deals
Air Canada
  • Air Canada
  • 7/11-31/12
  • 1 total stop
  • 6h 03m total
  • Windsor to Chicago
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Windsor to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Sat 7/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 365

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Tue 3/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 367

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Thu 5/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 367

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Thu 5/11

7:00 a.m.-5:40 p.m.

2 stops11h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 593

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Sun 1/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Sun 8/11

12:50 p.m.-6:45 p.m.

1 stop4h 55m

C$ 683

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Tue 20/10

10:05 a.m.-1:23 p.m.

1 stop4h 18m

Chicago O'Hare Intl

Tue 27/10

12:50 p.m.-6:45 p.m.

1 stop4h 55m

C$ 683

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Thu 5/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Thu 12/11

12:50 p.m.-6:45 p.m.

1 stop4h 55m

C$ 683

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Thu 5/11

7:00 a.m.-3:37 p.m.

3 stops33h 37m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 686

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Tue 3/11

10:35 a.m.-3:38 p.m.

1 stop6h 03m

Chicago O'Hare Intl

Tue 10/11

7:05 a.m.-6:45 p.m.

2 stops10h 40m

C$ 695

WindsorChicago

YQG Windsor - ORD Chicago O'Hare Intl

YQGORD

Windsor

Tue 3/11

7:00 a.m.-5:47 p.m.

3 stops35h 47m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 705

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/9

Showing 1-10 of 12 resultsSorted by cheapest first
1
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Best time to book a flight from Windsor to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Windsor with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Windsor to Chicago

No data available for this route at this time. Please check back soon.

Related info for your journey

  • What airport do you fly from for flights from Windsor to Chicago?

    If you book a flight to Chicago from Windsor, you will be flying from Windsor, which is the city’s only airport. Windsor (YQG) is located 8.0 km from the centre of Windsor. There are 0 flights from Windsor to Chicago per day from 0 different airlines.

  • How long is the flight from Windsor, Ontario to Chicago?

    Airlines like Air Canada fly from Windsor, Ontario to Chicago in about 6h 03m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 409 km.

  • Can I find deals for flights from Windsor to Chicago that include hotel bookings?

    Yes. In addition to deals on Windsor to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Windsor to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Windsor to Chicago.

  • Can I find deals for business class flights from Windsor to Chicago?

    Yes. Cheapflights offers flight deals from Windsor to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Windsor to Chicago flexibly with Cheapflights today.

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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Windsor today and book when prices fit your budget.

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