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Business Class Flight Deals from Chicago to Windsor from $371

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Up to 1 stop
    $853
  • Up to 2 stops
    $859

Airlines

  • Air Canada
    $853

Cabin Class

  • Business
    $853

Departure Airports

  • Chicago O Hare Airport
    $853

Arrival Airports

  • Windsor Airport
    $853

Layover Airports

  • Montreal Trudeau Airport
    $859
  • Toronto Pearson Airport
    $853

Best Price. GUARANTEED.

Exclusively for Priceline Members
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BUNDLE & SAVE
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On average save $240 per traveler
Air Canada Logo
Air Canada

09/05/25

ORD
5h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
4h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
5h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
5h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
4h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
4h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
4h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
5h 32m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$853
Air Canada Logo
Air Canada

09/05/25

ORD
7h 16m
YUL
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$859
Air Canada Logo
Air Canada

09/05/25

ORD
7h 16m
YUL
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$859
Air Canada Logo
Air Canada

09/05/25

ORD
7h 16m
YUL
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$859
Air Canada Logo
Air Canada

09/05/25

ORD
7h 16m
YUL
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$859
Air Canada Logo
Air Canada

09/05/25

ORD
11h 57m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
14h 21m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 57m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
7h 17m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
14h 21m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 57m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
7h 17m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 10m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 10m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
6h 9m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 57m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
7h 17m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
7h 17m
YYZ

09/05/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 10m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
14h 21m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 34m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
14h 21m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
11h 10m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$877
Air Canada Logo
Air Canada

09/05/25

ORD
14h 2m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
4h 19m
YYZ

09/12/25

ORD
$915
Air Canada Logo
Air Canada

09/05/25

ORD
14h 2m
YYZ

09/06/25

YQG
Air Canada Logo
Air Canada

09/12/25

YQG
5h 6m
YYZ

09/12/25

ORD
$915

Top Deals on flights Business Class from Chicago to Windsor

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

Air Canada Logo
Air Canada

Sep 6

ORD
4h 32m
YYZ

Sep 6

YQG

as low as

$371

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

Air Canada Logo
Air Canada

Sep 6

ORD
8h 27m
EWR
YYZ

Sep 6

YQG

as low as

$380

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

Air Canada Logo
Air Canada

Sep 6

ORD
14h 2m
YYZ

Sep 7

YQG

as low as

$394

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

Air Canada Logo
Air Canada

Sep 6

ORD
11h 57m
YYZ

Sep 7

YQG

as low as

$394

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

Air Canada Logo
Air Canada

Sep 6

ORD
11h 10m
YYZ

Sep 7

YQG

as low as

$432

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

Air Canada Logo
Air Canada

Sep 6

ORD
14h 21m
YYZ

Sep 7

YQG

as low as

$432

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

Air Canada Logo
Air Canada

Sep 6

ORD
7h 17m
YYZ

Sep 6

YQG

as low as

$470

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

Air Canada Logo
Air Canada

Sep 6

ORD
19h 17m
YYZ

Sep 7

YQG

as low as

$496

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

Air Canada Logo
Air Canada

Sep 6

ORD
21h 34m
YYZ

Sep 7

YQG

as low as

$496

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

Air Canada Logo
Air Canada

Sep 6

ORD
16h 32m
YYZ

Sep 7

YQG

as low as

$554

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

Air Canada Logo
Air Canada

Sep 6

ORD
20h 22m
YYZ

Sep 7

YQG

as low as

$554

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

Air Canada Logo
Air Canada

Sep 6

ORD
18h 22m
YYZ

Sep 7

YQG

as low as

$873

Frequently Asked Questions

What is the cheapest and fastest flight from Chicago to Windsor?
The cheapest flight is with Air Canada at $853, 1 stop, 4 hours 32 minutes. No faster option available.
What are all possible destination arrival airports?
The possible destination arrival airports for your flight from Chicago to Windsor are Windsor Airport, Toronto Pearson Airport, and Montreal Trudeau Airport.
What is the time difference between destination and arrival?
Chicago is in the Central Time Zone (CST), while Windsor is in the Eastern Time Zone (EST). Therefore, there is a one-hour time difference, with Windsor being one hour ahead of Chicago.
Is there a direct flight from Chicago to Windsor?
No, there is no direct flight from Chicago to Windsor. The cheapest available option is a 1 stop flight with Air Canada, costing $853 and requiring a layover at Toronto Pearson Airport.
Are there convenient layover flights from Chicago to Windsor?
Yes, there are convenient layover flights from Chicago O Hare to Windsor. The 1 stop flight with Air Canada is available at $853 with a layover at Toronto Pearson, and the 2 stops option is also available at $859 with layovers at Montreal Trudeau and Toronto Pearson.
What are the most convenient layover airports for the flight?
For your flight from Chicago to Windsor, the most convenient layover airport is Toronto Pearson, with Montreal Trudeau as an alternative for multiple stops.