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Find cheap flights from Chicago Midway Airport to Canada from C$ 161

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 23/5. 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
Wed 29/5
Wed 5/6

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Best Canada Flight Deals

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

Toronto
TorontodirectC$ 344
Ottawa
Ottawa1 stopC$ 504
Kelowna
Kelowna1 stopC$ 850
Québec City
Québec City1 stopC$ 504

Good to know

Low season

January

High season

November

Cheapest flight

C$ 161
Best time to beat the crowds (25% less expensive on average)
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 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$ 146 one-way - C$ 324 round-trip
  • Morning departure is around 14% 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.
7.4
Porter AirlinesOverall score based on 436 reviews
6.6Entertainment
7.6Boarding
7.4Food
7.5Comfort
8.2Crew
Airline reviews

Wish we had music during take off and landing like the last flight

10.0 ExcellentAnonymous, Apr. 2024EWR - YTZ
Read more about Porter Airlines reviews

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
3/6Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 344
29/5Wed
directPorter Airlines
1h 42mMDW-YTZ
5/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 346
22/5Wed
directPorter Airlines
1h 42mMDW-YTZ
29/5Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 347
28/5Tue
directPorter Airlines
1h 42mMDW-YTZ
29/5Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 351
29/5Wed
2 stops
11h 10mMDW-YTZ
31/5Fri
direct
1h 47mYTZ-MDW
C$ 391
15/5Wed
1 stop
20h 42mMDW-YVR
20/5Mon
1 stop
8h 57mYVR-MDW
C$ 394
27/7Sat
1 stopDelta
6h 48mMDW-YYZ
31/7Wed
1 stopDelta
3h 36mYYZ-MDW
C$ 458
31/5Fri
1 stopDelta
6h 37mMDW-YYZ
2/6Sun
1 stopDelta
4h 02mYYZ-MDW
C$ 459
5/6Wed
1 stopWestJet
12h 28mMDW-YYZ
12/6Wed
1 stopWestJet
11h 13mYYZ-MDW
C$ 499
14/6Fri
1 stopWestJet
10h 14mMDW-YYZ
17/6Mon
1 stopWestJet
13h 06mYYZ-MDW
C$ 525

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Recent one-way flight deals

23/5Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 161
22/5Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 164
8/5Wed
1 stop
30h 36mMDW-YYZ
C$ 164
7/5Tue
1 stop
18h 37mMDW-YVR
C$ 165
27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 165
18/6Tue
1 stopDelta
7h 48mMDW-YYZ
C$ 194
21/5Tue
1 stopDelta
8h 47mMDW-YUL
C$ 198
20/6Thu
1 stopWestJet
8h 14mMDW-YYZ
C$ 216
30/6Sun
1 stopWestJet
5h 10mMDW-YYZ
C$ 224
30/5Thu
3 stopsFlair Airlines
24h 00mMDW-YVR
C$ 373

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

3/5Fri
multi-stopDelta
12h 55mMDW-YYC
12/5Sun
multi-stopDelta
9h 12mYYC-MDW
C$ 461
3/5Fri
multi-stopKLM
10h 36mMDW-YYC
12/5Sun
multi-stopKLM
9h 12mYYC-MDW
C$ 551
2/5Thu
multi-stop
18h 46mMDW-YVR
6/5Mon
multi-stop
9h 50mYVR-MDW
C$ 595
30/4Tue
multi-stop
17h 31mMDW-YVR
3/5Fri
multi-stop
13h 39mYVR-MDW
C$ 596
2/5Thu
multi-stop
18h 46mMDW-YVR
6/5Mon
multi-stop
12h 05mYVR-MDW
C$ 597
2/5Thu
multi-stop
18h 46mMDW-YVR
4/5Sat
multi-stop
13h 09mYVR-MDW
C$ 605
1/5Wed
directPorter Airlines
1h 42mMDW-YTZ
18/5Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 615
3/5Fri
directPorter Airlines
1h 42mMDW-YTZ
6/5Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 637
1/5Wed
multi-stopWestJet
6h 00mMDW-YYZ
18/5Sat
multi-stopWestJet
5h 25mYYZ-MDW
C$ 715
3/5Fri
multi-stopWestJet
5h 54mMDW-YYZ
7/5Tue
multi-stopWestJet
4h 57mYYZ-MDW
C$ 731

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Chicago Midway Airport - Canada Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Canada - Chicago Midway Airport

Cabin classes:

C$ 171