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$99 Find Cheap Flights from Chicago Midway Airport to Canada

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Canada departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

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Best Canada Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Toronto
Torontononstop$252
Calgary
Calgary1 stop$250
Halifax
Halifax2 stops$306
Ottawa
Ottawa1 stop$405
Québec City
Québec City1 stop$633
Winnipeg
Winnipeg1 stop$451
St. John's
St. John's3 stops$623
Saskatoon
Saskatoon1 stop$782
Thunder Bay
Thunder Bay1 stop$477

Good to know

Low season

February

High season

December

Cheapest flight

$99
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago Midway Airport to Calgary

FAQs - booking Canada flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Canada?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Canada.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Canada?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Canada from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Canada?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Canada with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Canada?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Canada from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Canada

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Toronto $169 one-way - $272 round-trip
  • Morning departure is around 10% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airline flying from Midway to Canada

Need help choosing which airline to fly with from Midway to Canada? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
Porter AirlinesOverall score based on 288 reviews
8.1Boarding
6.9Entertainment
7.9Comfort
7.6Food
8.6Crew
Airline reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

1/24Fri
1 stop
11h 47mMDW-YVR
1/28Tue
2 stops
19h 51mYVR-MDW
$241
1/20Mon
1 stopDelta
8h 27mMDW-YYC
1/24Fri
1 stopDelta
10h 12mYYC-MDW
$250
12/12Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
12/15Sun
nonstopPorter Airlines
1h 50mYTZ-MDW
$252
12/12Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
12/15Sun
nonstopPorter Airlines
1h 50mYTZ-MDW
$255
1/19Sun
1 stop
11h 12mMDW-YYC
1/29Wed
1 stop
8h 11mYYC-MDW
$256
12/12Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
12/15Sun
nonstopPorter Airlines
1h 50mYTZ-MDW
$256
12/12Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
12/15Sun
nonstopPorter Airlines
1h 50mYTZ-MDW
$257
1/30Thu
1 stopWestJet
11h 52mMDW-YYZ
1/31Fri
1 stopWestJet
20h 51mYYZ-MDW
$394
12/12Thu
1 stopWestJet
12h 56mMDW-YYZ
12/16Mon
1 stopWestJet
13h 02mYYZ-MDW
$397
1/4Sat
nonstopAPG Airlines
1h 42mMDW-YTZ
1/11Sat
nonstopAPG Airlines
1h 50mYTZ-MDW
$486

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Recent one-way flight deals

1/11Sat
1 stopDelta
10h 34mMDW-YYC
$99
1/11Sat
2 stopsDelta
12h 19mMDW-YYC
$104
12/17Tue
1 stop
8h 44mMDW-YYC
$112
1/22Wed
2 stops
16h 15mMDW-YVR
$116
12/15Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$121
12/19Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$123
12/18Wed
1 stopWestJet
12h 56mMDW-YYZ
$150
12/21Sat
nonstopAir Transat
1h 42mMDW-YTZ
$161
12/17Tue
1 stopWestJet
10h 11mMDW-YUL
$176
3/19Wed
nonstopAir Transat
1h 42mMDW-YTZ
$214

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

11/26Tue
multi-stopWestJet
17h 24mMDW-YYZ
11/29Fri
multi-stopWestJet
13h 02mYYZ-MDW
$414
11/26Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
11/29Fri
nonstopPorter Airlines
1h 50mYTZ-MDW
$422
11/26Tue
multi-stop
42h 34mMDW-YVR
11/29Fri
multi-stop
10h 11mYVR-MDW
$459
11/26Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
11/28Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
$462
11/25Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
11/29Fri
nonstopPorter Airlines
1h 50mYTZ-MDW
$484
11/26Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
11/28Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
$488
11/26Tue
multi-stop
16h 40mMDW-YYZ
11/29Fri
multi-stop
13h 02mYYZ-MDW
$508
11/25Mon
multi-stopPorter Airlines
4h 30mMDW-YUL
11/29Fri
multi-stopPorter Airlines
5h 50mYUL-MDW
$521
11/25Mon
multi-stopDelta
12h 04mMDW-YYC
11/29Fri
multi-stopDelta
13h 46mYYC-MDW
$595
11/23Sat
multi-stopDelta
8h 17mMDW-YYZ
11/26Tue
multi-stopDelta
7h 57mYYZ-MDW
$662

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Everything you need to know for your flight from Midway to Canada

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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