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C$ 130 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 6/3. 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.
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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$ 284
Ottawa
Ottawa1 stopC$ 423
Québec City
Québec City1 stopC$ 819

Good to know

Low season

January

High season

April

Cheapest flight

C$ 130
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to Toronto Island

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$ 259 one-way - C$ 585 round-trip
  • High season is considered to be September, October and November. The cheapest month to fly from Chicago is January.
  • Morning departure is around 31% 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.
7.9
Porter AirlinesOverall score based on 277 reviews
8.7Crew
6.9Entertainment
8.2Boarding
7.6Food
8.0Comfort
Airline reviews

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

8.0 ExcellentJason, Dec 2024YUL - YHZ
Read more Porter Airlines reviews

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

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.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

13/2Thu
directPorter Airlines
1h 42mMDW-YTZ
16/2Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 284
25/2Tue
directPorter Airlines
1h 42mMDW-YTZ
27/2Thu
directPorter Airlines
1h 50mYTZ-MDW
C$ 286
13/2Thu
direct
1h 42mMDW-YTZ
16/2Sun
direct
1h 50mYTZ-MDW
C$ 314
22/3Sat
directAir Transat
1h 42mMDW-YTZ
26/3Wed
directAir Transat
1h 50mYTZ-MDW
C$ 346
10/2Mon
1 stopDelta
8h 27mMDW-YYC
16/2Sun
1 stopDelta
10h 08mYYC-MDW
C$ 360
8/2Sat
1 stopDelta
10h 28mMDW-YYC
11/2Tue
1 stopDelta
5h 07mYYC-MDW
C$ 361
4/3Tue
2 stops
17h 25mMDW-YVR
10/3Mon
2 stops
19h 31mYVR-MDW
C$ 383
13/2Thu
1 stopKLM
8h 41mMDW-YYZ
16/2Sun
1 stopKLM
5h 17mYYZ-MDW
C$ 432
20/2Thu
2 stopsKLM
13h 54mMDW-YYC
27/2Thu
1 stopKLM
5h 07mYYC-MDW
C$ 495
30/5Fri
directAir Transat
1h 42mMDW-YTZ
2/6Mon
directAir Transat
1h 50mYTZ-MDW
C$ 507

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Recent one-way flight deals

6/3Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 130
18/2Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 134
12/2Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 135
4/3Tue
2 stops
18h 38mMDW-YYZ
C$ 143
3/2Mon
2 stopsDelta
12h 20mMDW-YYC
C$ 153
22/2Sat
1 stop
16h 50mMDW-YVR
C$ 157
3/2Mon
1 stopDelta
8h 27mMDW-YYC
C$ 160
26/2Wed
1 stopKLM
8h 27mMDW-YYC
C$ 179
11/3Tue
1 stopWestJet
6h 13mMDW-YYZ
C$ 209
11/2Tue
2 stopsWestJet
12h 14mMDW-YYZ
C$ 238

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

23/1Thu
multi-stopDelta
8h 27mMDW-YYC
30/1Thu
multi-stopDelta
10h 12mYYC-MDW
C$ 409
23/1Thu
multi-stopDelta
12h 19mMDW-YYC
30/1Thu
multi-stopDelta
10h 12mYYC-MDW
C$ 423
26/1Sun
multi-stopDelta
12h 19mMDW-YYC
31/1Fri
multi-stopDelta
5h 11mYYC-MDW
C$ 454
23/1Thu
multi-stopDelta
12h 19mMDW-YYC
30/1Thu
multi-stopDelta
10h 39mYYC-MDW
C$ 469
23/1Thu
multi-stopPorter Airlines
7h 20mMDW-YHZ
25/1Sat
multi-stopPorter Airlines
5h 35mYHZ-MDW
C$ 603
23/1Thu
multi-stopPorter Airlines
7h 20mMDW-YHZ
25/1Sat
multi-stopPorter Airlines
7h 40mYHZ-MDW
C$ 610
24/1Fri
multi-stop
24h 10mMDW-YEG
26/1Sun
multi-stop
13h 58mYEG-MDW
C$ 680
24/1Fri
multi-stop
16h 47mMDW-YEG
26/1Sun
multi-stop
13h 58mYEG-MDW
C$ 681
23/1Thu
multi-stopWestJet
21h 23mMDW-YYZ
2/2Sun
multi-stopWestJet
7h 16mYYZ-MDW
C$ 788
24/1Fri
multi-stopWestJet
11h 52mMDW-YYZ
27/1Mon
multi-stopWestJet
7h 16mYYZ-MDW
C$ 789

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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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