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Flight Deals from Chicago to Windsor from $176

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Stops

  • Up to 1 stop
    $422
  • Up to 2 stops
    $492

Airlines

  • Air Canada
    $422
  • United Airlines
    $714

Cabin Class

  • Economy
    $422

Departure Airports

  • Chicago O Hare Airport
    $422

Arrival Airports

  • Windsor Airport
    $422

Layover Airports

  • Montreal Trudeau Airport
    $492
  • Toronto Pearson Airport
    $422

Best Price. GUARANTEED.

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

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 9m
YYZ

09/17/25

ORD
$422
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 19m
YYZ

09/17/25

ORD
$422
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 34m
YYZ

09/17/25

ORD
$422
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
10h 34m
YYZ

09/17/25

ORD
$446
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 9m
YYZ

09/17/25

ORD
$446
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 19m
YYZ

09/17/25

ORD
$446
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 34m
YYZ

09/17/25

ORD
$446
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
8h 38m
YYZ

09/17/25

ORD
$446
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
8h 38m
YYZ

09/17/25

ORD
$470
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
10h 34m
YYZ

09/17/25

ORD
$470
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
11h 16m
YYZ
YUL

09/17/25

ORD
$492
Air Canada Logo
Air Canada

09/10/25

ORD
11h 57m
YYZ

09/11/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
11h 16m
YYZ
YUL

09/17/25

ORD
$516
Air Canada Logo
Air Canada

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 19m
YYZ

09/17/25

ORD
$519
Air Canada Logo
Air Canada

09/10/25

ORD
4h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
5h 6m
YYZ

09/17/25

ORD
$519
Air Canada Logo
Air Canada

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
5h 6m
YYZ

09/17/25

ORD
$519
Air Canada Logo
Air Canada

09/10/25

ORD
7h 6m
YUL
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 9m
YYZ

09/17/25

ORD
$524
Air Canada Logo
Air Canada

09/10/25

ORD
7h 6m
YUL
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 53m
YYZ

09/17/25

ORD
$524
Air Canada Logo
Air Canada

09/10/25

ORD
7h 6m
YUL
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 34m
YYZ

09/17/25

ORD
$524
Air Canada Logo
Air Canada

09/10/25

ORD
7h 6m
YUL
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 19m
YYZ

09/17/25

ORD
$524
Air Canada Logo
Air Canada

09/10/25

ORD
7h 6m
YUL
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
5h 6m
YYZ

09/17/25

ORD
$524
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
5h 6m
YYZ

09/17/25

ORD
$714
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 19m
YYZ

09/17/25

ORD
$714
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
4h 34m
YYZ

09/17/25

ORD
$714
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 9m
YYZ

09/17/25

ORD
$714
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
6h 53m
YYZ

09/17/25

ORD
$714
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
10h 34m
YYZ

09/17/25

ORD
$738
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
8h 38m
YYZ

09/17/25

ORD
$738
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
17h 6m
YYZ
YUL

09/18/25

ORD
$776
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
23h 6m
YYZ
YUL

09/18/25

ORD
$776
United Airlines Logo
United Airlines

09/10/25

ORD
5h 22m
YYZ

09/10/25

YQG
Air Canada Logo
Air Canada

09/17/25

YQG
20h 28m
YYZ
YUL

09/18/25

ORD
$776

Top Deals on flights from Chicago to Windsor

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

Air Canada Logo
Air Canada

Sep 10

ORD
4h 22m
YYZ

Sep 10

YQG

as low as

$176

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

Air Canada Logo
Air Canada

Sep 10

ORD
11h 57m
YYZ

Sep 11

YQG

as low as

$200

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

Air Canada Logo
Air Canada

Sep 10

ORD
5h 22m
YYZ

Sep 10

YQG

as low as

$224

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

Air Canada Logo
Air Canada

Sep 10

ORD
7h 6m
YUL
YYZ

Sep 10

YQG

as low as

$230

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

Air Canada Logo
Air Canada

Sep 10

ORD
17h 9m
EWR
YYZ

Sep 11

YQG

as low as

$234

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

Air Canada Logo
Air Canada

Sep 10

ORD
8h 17m
EWR
YYZ

Sep 10

YQG

as low as

$234

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

Air Canada Logo
Air Canada

Sep 10

ORD
11h 10m
YYZ

Sep 11

YQG

as low as

$248

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

Air Canada Logo
Air Canada

Sep 10

ORD
7h 7m
YYZ

Sep 10

YQG

as low as

$248

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

Air Canada Logo
Air Canada

Sep 10

ORD
20h 11m
YOW
YYZ

Sep 11

YQG

as low as

$282

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

Air Canada Logo
Air Canada

Sep 10

ORD
14h 2m
YYZ

Sep 11

YQG

as low as

$286

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

Air Canada Logo
Air Canada

Sep 10

ORD
17h 5m
YYZ

Sep 11

YQG

as low as

$291

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

Air Canada Logo
Air Canada

Sep 10

ORD
19h 32m
IAD
YYZ

Sep 11

YQG

as low as

$303

Frequently Asked Questions

What are all possible destination arrival airports?
The possible destination arrival airports are Windsor Airport and Toronto Pearson Airport.
What is the time difference between destination and arrival?
Your arrival in Windsor will be in a different time zone than Chicago, resulting in a time difference. Ensure to account for this when planning your activities upon arrival.
Is there a direct flight from Chicago to Windsor?
There is no direct flight from Chicago to Windsor. The cheapest available option is a 1 stop flight with Air Canada for $422, with layovers at Toronto Pearson Airport.
Are there convenient layover flights from Chicago to Windsor?
Yes, there are convenient layover flights from Chicago to Windsor. Air Canada offers a 1 stop flight for $422, and United Airlines offers a 1 stop flight for $714. Additionally, Air Canada has a 2 stops option priced at $524.
What are the most convenient layover airports for my flight?
For your flight from Chicago to Windsor, the most convenient layover airports are Toronto Pearson Airport and Montreal Trudeau Airport, as they facilitate smoother connections with both Air Canada and United Airlines.
What is the cheapest and fastest flight from Chicago to Windsor?
The cheapest flight is with Air Canada at $422, 4 hours 22 minutes. No faster option is available.