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Flight Deals from Windsor to Chicago from $177

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Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

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

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If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

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Stops

  • Up to 1 stop
    $405
  • Up to 2 stops
    $463

Airlines

  • Air Canada
    $405

Cabin Class

  • Economy
    $405

Departure Airports

  • Windsor Airport
    $405

Arrival Airports

  • Chicago O Hare Airport
    $405

Layover Airports

  • Ottawa Macdonald-Cartier International Airport
    $486
  • Toronto Pearson Airport
    $405
  • Washington Dulles Airport
    $463

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Air Canada Logo
Air Canada

07/25/25

YQG
4h 8m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$405
Air Canada Logo
Air Canada

07/25/25

YQG
7h 5m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$448
Air Canada Logo
Air Canada

07/25/25

YQG
6h 45m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$448
Air Canada Logo
Air Canada

07/25/25

YQG
4h 56m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$448
Air Canada Logo
Air Canada

07/25/25

YQG
4h 8m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$460
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$463
Air Canada Logo
Air Canada

07/25/25

YQG
6h 45m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$475
Air Canada Logo
Air Canada

07/25/25

YQG
4h 56m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$475
Air Canada Logo
Air Canada

07/25/25

YQG
7h 5m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$475
Air Canada Logo
Air Canada

07/25/25

YQG
4h 56m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
11h 13m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
6h 45m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 32m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
6h 45m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
11h 13m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
7h 5m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
11h 13m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
7h 5m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 32m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
4h 56m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 32m
YYZ

08/02/25

YQG
$485
Air Canada Logo
Air Canada

07/25/25

YQG
7h 5m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
4h 24m
YYZ

08/01/25

YQG
$486
Air Canada Logo
Air Canada

07/25/25

YQG
4h 56m
YYZ

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
4h 24m
YYZ

08/01/25

YQG
$486
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
12h 2m
YYZ

08/02/25

YQG
$486
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$490
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 32m
YYZ

08/02/25

YQG
$500
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
11h 13m
YYZ

08/02/25

YQG
$500
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
4h 24m
YYZ

08/01/25

YQG
$501
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 7m
YYZ

08/02/25

YQG
$513
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
11h 13m
YYZ

08/02/25

YQG
$524
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
14h 32m
YYZ

08/02/25

YQG
$524
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
4h 24m
YYZ

08/01/25

YQG
$525
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
17h 57m
YYZ

08/02/25

YQG
$607
Air Canada Logo
Air Canada

07/25/25

YQG
8h 30m
YYZ
IAD

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
16h 37m
YYZ

08/02/25

YQG
$622
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
17h 57m
YYZ

08/02/25

YQG
$631
Air Canada Logo
Air Canada

07/25/25

YQG
9h 48m
YYZ
YOW

07/25/25

ORD
Air Canada Logo
Air Canada

08/01/25

ORD
16h 37m
YYZ

08/02/25

YQG
$645

Top Deals on flights from Windsor to Chicago

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

Air Canada Logo
Air Canada

Jul 24

YQG
5h 59m
YYZ

Jul 24

ORD

as low as

$177

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

Air Canada Logo
Air Canada

Jul 24

YQG
4h 29m
YYZ

Jul 24

ORD

as low as

$198

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

Air Canada Logo
Air Canada

Jul 24

YQG
7h 5m
YYZ

Jul 24

ORD

as low as

$218

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

Air Canada Logo
Air Canada

Jul 24

YQG
8h 30m
YYZ
IAD

Jul 24

ORD

as low as

$234

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

Air Canada Logo
Air Canada

Jul 24

YQG
14h 25m
YYZ
IAD

Jul 24

ORD

as low as

$249

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

Air Canada Logo
Air Canada

Jul 24

YQG
4h 8m
YYZ

Jul 24

ORD

as low as

$274

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

Air Canada Logo
Air Canada

Jul 24

YQG
4h 56m
YYZ

Jul 24

ORD

as low as

$280

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

Air Canada Logo
Air Canada

Jul 24

YQG
6h 45m
YYZ

Jul 24

ORD

as low as

$280

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

Air Canada Logo
Air Canada

Jul 24

YQG
10h 24m
YYZ

Jul 24

ORD

as low as

$291

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

Air Canada Logo
Air Canada

Jul 24

YQG
13h
YYZ

Jul 24

ORD

as low as

$304

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

Air Canada Logo
Air Canada

Jul 24

YQG
18h 59m
YYZ

Jul 25

ORD

as low as

$309

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

Air Canada Logo
Air Canada

Jul 24

YQG
9h 48m
YYZ
YOW

Jul 24

ORD

as low as

$314