Find flights
Deals
When to book
FAQs & Tips
Airlines

C$ 138 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 14/1. 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

Search hundreds of travel sites at once for deals on flights to Canada

Best Canada Flight Deals

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

Toronto
TorontodirectC$ 324
Ottawa
Ottawa1 stopC$ 452
Québec City
Québec City1 stopC$ 734

Good to know

Low season

February

High season

December
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly and prices are also 12% 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 to Canada from Chicago Midway Airport 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 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 C$ 160 one-way - C$ 386 round-trip
  • Morning departure is around 6% 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.
7.8
Porter AirlinesOverall score based on 293 reviews
7.6Food
8.5Crew
8.0Boarding
7.9Comfort
6.9Entertainment
Airline reviews

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

4.0 OkayAnonymous, Oct 2024YYZ - YOW
Read more Porter Airlines reviews

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

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

4/12Wed
directPorter Airlines
1h 42mMDW-YTZ
8/12Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 324
24/12Tue
directPorter Airlines
1h 42mMDW-YTZ
9/1Thu
directPorter Airlines
1h 50mYTZ-MDW
C$ 325
7/12Sat
directPorter Airlines
1h 42mMDW-YTZ
10/12Tue
directPorter Airlines
1h 50mYTZ-MDW
C$ 332
4/12Wed
2 stopsDelta
12h 04mMDW-YYC
10/12Tue
1 stopDelta
5h 31mYYC-MDW
C$ 360
6/12Fri
direct
1h 42mMDW-YTZ
7/12Sat
direct
1h 50mYTZ-MDW
C$ 363
4/12Wed
direct
1h 42mMDW-YTZ
9/12Mon
direct
1h 50mYTZ-MDW
C$ 364
4/12Wed
2 stopsDelta
12h 04mMDW-YYC
10/12Tue
2 stopsDelta
9h 32mYYC-MDW
C$ 367
5/12Thu
1 stopKLM
6h 08mMDW-YYZ
8/12Sun
1 stopKLM
3h 45mYYZ-MDW
C$ 450
3/12Tue
directAir Transat
1h 42mMDW-YTZ
5/12Thu
directAir Transat
1h 50mYTZ-MDW
C$ 478
2/12Mon
directAir Transat
1h 42mMDW-YTZ
7/12Sat
directAir Transat
1h 50mYTZ-MDW
C$ 482

Search by stops

Search by airline

Search by price

Recent one-way flight deals

14/1Tue
1 stopDelta
8h 27mMDW-YYC
C$ 138
18/12Wed
1 stop
22h 40mMDW-YEG
C$ 142
4/12Wed
2 stopsDelta
12h 04mMDW-YYC
C$ 145
16/12Mon
2 stops
22h 17mMDW-YEG
C$ 145
30/11Sat
1 stopPorter Airlines
4h 20mMDW-YUL
C$ 156
27/11Wed
1 stopPorter Airlines
4h 30mMDW-YUL
C$ 158
24/12Tue
1 stopWestJet
5h 18mMDW-YYZ
C$ 221
6/12Fri
1 stopWestJet
17h 27mMDW-YYZ
C$ 222
25/11Mon
directAir Transat
1h 42mMDW-YTZ
C$ 229
14/11Thu
directAir Transat
1h 42mMDW-YTZ
C$ 327

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Canada

Last minute flight, train and bus deals

9/11Sat
directPorter Airlines
1h 42mMDW-YTZ
11/11Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 653
7/11Thu
directPorter Airlines
1h 42mMDW-YTZ
14/11Thu
directPorter Airlines
1h 50mYTZ-MDW
C$ 660
9/11Sat
directAir Transat
1h 42mMDW-YTZ
19/11Tue
directAir Transat
1h 50mYTZ-MDW
C$ 701
8/11Fri
direct
1h 42mMDW-YTZ
14/11Thu
direct
1h 50mYTZ-MDW
C$ 724
8/11Fri
multi-stop
4h 30mMDW-YUL
17/11Sun
multi-stop
11h 54mYUL-MDW
C$ 730
9/11Sat
multi-stopWestJet
12h 02mMDW-YYZ
11/11Mon
multi-stopWestJet
16h 17mYYZ-MDW
C$ 770
8/11Fri
multi-stopDelta
4h 09mMDW-YYZ
13/11Wed
multi-stopDelta
5h 47mYYZ-MDW
C$ 852
9/11Sat
multi-stopWestJet
12h 02mMDW-YYZ
12/11Tue
multi-stopWestJet
16h 17mYYZ-MDW
C$ 869
9/11Sat
multi-stopDelta
4h 15mMDW-YUL
16/11Sat
multi-stopDelta
9h 51mYUL-MDW
C$ 890
9/11Sat
directAir Transat
1h 42mMDW-YTZ
15/11Fri
directAir Transat
1h 50mYTZ-MDW
C$ 1,517

Search by stops

Search by airline

Search by price

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

Information on your arrival and departure airports