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C$ 142 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 4/2. 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 from Midway

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

Toronto
TorontodirectC$ 376
Ottawa
Ottawa1 stopC$ 519
Québec City
Québec City1 stopC$ 851

Good to know

Low season

February

High season

December
Best time to beat the crowds (20% less expensive on average)
Most popular time to fly and prices are also 7% lower on average.

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 from Chicago Midway Airport to Canada is likely to change within 7 days, so travellers 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 from Chicago Midway Airport to Canada with an airline and back 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 from Chicago Midway Airport to Canada 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 C$ 421 one-way - C$ 482 round-trip
  • High season is considered to be September, October and November. The cheapest month to fly from Chicago is February.
  • Morning departure is around 7% cheaper 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.
7.9
Porter AirlinesOverall score based on 283 reviews
8.1Boarding
7.0Entertainment
8.7Crew
7.6Food
8.0Comfort
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

4/2Tue
1 stopDelta
8h 27mMDW-YYC
11/2Tue
1 stopDelta
5h 07mYYC-MDW
C$ 358
5/2Wed
2 stopsDelta
12h 20mMDW-YYC
12/2Wed
1 stopDelta
10h 08mYYC-MDW
C$ 371
13/2Thu
directPorter Airlines
1h 42mMDW-YTZ
16/2Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 376
3/2Mon
1 stop
11h 47mMDW-YVR
10/2Mon
2 stops
17h 41mYVR-MDW
C$ 379
16/2Sun
directPorter Airlines
1h 42mMDW-YTZ
17/2Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 381
3/2Mon
1 stop
11h 47mMDW-YVR
10/2Mon
2 stops
17h 41mYVR-MDW
C$ 389
4/2Tue
1 stopWestJet
8h 41mMDW-YYZ
11/2Tue
1 stopWestJet
7h 12mYYZ-MDW
C$ 451
28/1Tue
1 stopWestJet
21h 23mMDW-YYZ
29/1Wed
1 stopWestJet
23h 01mYYZ-MDW
C$ 576
5/6Thu
directAir Transat
1h 42mMDW-YTZ
8/6Sun
directAir Transat
1h 50mYTZ-MDW
C$ 891
5/2Wed
directAir Transat
1h 42mMDW-YTZ
9/2Sun
directAir Transat
1h 50mYTZ-MDW
C$ 977

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Recent one-way flight deals

4/2Tue
1 stopDelta
8h 27mMDW-YYC
C$ 142
4/2Tue
2 stopsDelta
12h 20mMDW-YYC
C$ 149
8/1Wed
2 stops
16h 15mMDW-YVR
C$ 152
27/1Mon
2 stops
18h 04mMDW-YYZ
C$ 157
16/2Sun
1 stopPorter Airlines
5h 10mMDW-YHZ
C$ 184
18/1Sat
2 stopsPorter Airlines
7h 20mMDW-YHZ
C$ 187
16/1Thu
1 stopWestJet
11h 52mMDW-YYZ
C$ 266
4/2Tue
2 stopsWestJet
16h 01mMDW-YHZ
C$ 272
4/1Sat
directAir Transat
1h 42mMDW-YTZ
C$ 293
6/6Fri
directAir Transat
1h 42mMDW-YTZ
C$ 445

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

24/12Tue
directPorter Airlines
1h 42mMDW-YTZ
11/1Sat
directPorter Airlines
1h 50mYTZ-MDW
C$ 619
23/12Mon
directPorter Airlines
1h 42mMDW-YTZ
12/1Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 621
24/12Tue
directPorter Airlines
1h 42mMDW-YTZ
12/1Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 624
23/12Mon
multi-stopWestJet
5h 04mMDW-YYZ
12/1Sun
multi-stopWestJet
7h 16mYYZ-MDW
C$ 680
23/12Mon
multi-stop
9h 58mMDW-YTZ
12/1Sun
direct
1h 50mYTZ-MDW
C$ 685
24/12Tue
multi-stopWestJet
5h 18mMDW-YYZ
11/1Sat
multi-stopWestJet
5h 06mYYZ-MDW
C$ 730
26/12Thu
multi-stop
5h 04mMDW-YYZ
10/1Fri
multi-stop
8h 23mYYZ-MDW
C$ 740
27/12Fri
directAir Transat
1h 42mMDW-YTZ
31/12Tue
directAir Transat
1h 50mYTZ-MDW
C$ 779
24/12Tue
multi-stopDelta
5h 18mMDW-YYZ
12/1Sun
multi-stopDelta
6h 23mYYZ-MDW
C$ 795
23/12Mon
multi-stopDelta
5h 04mMDW-YYZ
3/1Fri
multi-stopDelta
7h 19mYYZ-MDW
C$ 805

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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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