$380 Business Class Flight Deals from Windsor to Chicago

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Stops

Up to 1 stop
$974
Up to 2 stops
$979

Airlines

Air Canada
$974

Cabin Class

Business
$974

Departure Airports

Windsor Airport
$974

Arrival Airports

Chicago O Hare Airport
$974

Layover Airports

Montreal Trudeau Airport
$979
Newark Liberty Airport
$984
Ottawa Macdonald-Cartier International Airport
$996
Toronto Pearson Airport
$974

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On average save $240 per traveler

Air Canada

09/24/25

4:00pm

YQG

18h 55m

YYZ

09/25/25

9:55am

ORD

Air Canada

10/01/25

8:55am

ORD

5h 17m

YYZ

10/01/25

3:12pm

YQG

^$974

Air Canada

09/24/25

4:00pm

YQG

16h 58m

YYZ

09/25/25

7:58am

ORD

Air Canada

10/01/25

8:55am

ORD

5h 17m

YYZ

10/01/25

3:12pm

YQG

^$974

Air Canada

09/24/25

4:00pm

YQG

18h 55m

YYZ

09/25/25

9:55am

ORD

Air Canada

10/01/25

7:11am

ORD

7h 1m

YUL

YYZ

10/01/25

3:12pm

YQG

^$979

Air Canada

09/24/25

4:00pm

YQG

16h 58m

YYZ

09/25/25

7:58am

ORD

Air Canada

10/01/25

7:11am

ORD

7h 1m

YUL

YYZ

10/01/25

3:12pm

YQG

^$979

Air Canada

09/24/25

4:00pm

YQG

16h 58m

YYZ

09/25/25

7:58am

ORD

Air Canada

10/01/25

6:00am

ORD

8h 12m

EWR

YYZ

10/01/25

3:12pm

YQG

^$984

Air Canada

09/24/25

4:00pm

YQG

17h

YYZ

YOW

09/25/25

8:00am

ORD

Air Canada

10/01/25

8:55am

ORD

5h 17m

YYZ

10/01/25

3:12pm

YQG

^$996

Air Canada

09/24/25

4:00pm

YQG

17h 1m

YYZ

YUL

09/25/25

8:01am

ORD

Air Canada

10/01/25

8:55am

ORD

5h 17m

YYZ

10/01/25

3:12pm

YQG

^$1001

Air Canada

09/24/25

4:00pm

YQG

7h 7m

YYZ

09/24/25

10:07pm

ORD

Air Canada

10/01/25

8:55am

ORD

5h 17m

YYZ

10/01/25

3:12pm

YQG

^$1171

Air Canada

09/24/25

4:00pm

YQG

7h 7m

YYZ

09/24/25

10:07pm

ORD

Air Canada

10/01/25

7:11am

ORD

7h 1m

YUL

YYZ

10/01/25

3:12pm

YQG

^$1176

Air Canada

09/24/25

4:00pm

YQG

7h 7m

YYZ

09/24/25

10:07pm

ORD

Air Canada

10/01/25

6:00am

ORD

8h 12m

EWR

YYZ

10/01/25

3:12pm

YQG

^$1181

Air Canada

09/24/25

4:00pm

YQG

7h 7m

YYZ

09/24/25

10:07pm

ORD

Air Canada

10/01/25

7:10am

ORD

7h 2m

YYZ

10/01/25

3:12pm

YQG

^$1194

Top Deals on flights Business Class from Windsor to Chicago

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

6h 53m

YYZ

Sep 25

3:48pm

ORD

as low as

^$380

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

5h 6m

YYZ

Sep 25

2:01pm

ORD

as low as

^$380

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

4:00pm

YQG

17h

YYZ

YOW

Sep 26

8:00am

ORD

as low as

^$387

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

9h 59m

YYZ

YOW

Sep 25

6:54pm

ORD

as low as

^$404

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

8h 38m

YYZ

Sep 25

5:33pm

ORD

as low as

^$498

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

9h 46m

YYZ

YUL

Sep 25

6:41pm

ORD

as low as

^$576

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

11h 16m

YYZ

YUL

Sep 25

8:11pm

ORD

as low as

^$641

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

9:55am

YQG

14h 35m

YYZ

EWR

Sep 25

11:30pm

ORD

as low as

^$642

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

4:00pm

YQG

23h 1m

YYZ

Sep 26

2:01pm

ORD

as low as

^$662

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

4:00pm

YQG

16h 58m

YYZ

Sep 26

7:58am

ORD

as low as

^$662

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada

Sep 25

4:00pm

YQG

18h 55m

YYZ

Sep 26

9:55am

ORD

as low as

^$662

Frequently Asked Questions

What are the cheapest and fastest flights from Windsor to Chicago?

The cheapest flight is with Air Canada at $974, taking 16 hours 58 minutes. The fastest flight is also with Air Canada at $1171, taking 7 hours 7 minutes.

What are all possible destination arrival airports?

The possible destination arrival airport is Chicago O'Hare Airport, along with layover airports being Toronto Pearson Airport and Ottawa Macdonald-Cartier International Airport.

What is the time difference between destination and arrival?

Chicago is in the Central Time Zone, which is generally one hour behind Windsor. When you arrive, you should adjust your schedule accordingly.

Is there a direct flight from Windsor to Chicago?

There is no direct flight from Windsor to Chicago. The available flights include a 1 stop flight with Air Canada priced at $974 or $1171, both with layovers at Toronto Pearson Airport.

Are there convenient layover flights from Windsor to Chicago?

Yes, convenient layover flights from Windsor to Chicago are available. Air Canada offers a 1 stop flight for $974 and a 2 stops flight for $996, both with layovers at Toronto Pearson Airport.

What are the most convenient layover airports for the flight?

For your flight from Windsor to Chicago, the most convenient layover airport is Toronto Pearson Airport. If considering additional stops, Ottawa Macdonald-Cartier International Airport is also an option.

Flights to Chicago

Top Destinations

Origins

Return flights

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➔ Business Class Flights From Chicago To Windsor

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Business Class Flight Deals from Windsor to Chicago from $380

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights Business Class from Windsor to Chicago

Frequently Asked Questions

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