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Find cheap flights from Chicago Midway Airport to Canada from $108

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 9/20. 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
Fri 6/21
Fri 6/28

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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$245
Calgary
Calgary1 stop$284
Halifax
Halifax1 stop$289
Ottawa
Ottawa1 stop$379
Québec City
Québec City1 stop$395
Winnipeg
Winnipeg2 stops$429
St. John's
St. John's2 stops$560
Saskatoon
Saskatoon1 stop$677

Good to know

Low season

November

High season

July

Cheapest flight

$108
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 3% increase in price.
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 $132 one-way - $266 round-trip
  • Morning departure is around 23% 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 airlines 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.
8.0
DeltaOverall score based on 10585 reviews
7.4Food
7.9Comfort
8.6Crew
8.0Entertainment
8.2Boarding
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

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

6/11Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$245
6/8Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
6/12Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$246
6/29Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
7/6Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$248
7/26Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
7/26Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$249
6/5Wed
1 stop
11h 56mMDW-YYC
6/8Sat
1 stop
9h 30mYYC-MDW
$284
9/4Wed
1 stop
15h 28mMDW-YVR
9/11Wed
1 stop
9h 24mYVR-MDW
$292
10/1Tue
1 stopDelta
7h 43mMDW-YYC
10/6Sun
1 stopDelta
5h 12mYYC-MDW
$303
6/5Wed
1 stopDelta
7h 34mMDW-YYZ
6/11Tue
1 stopDelta
3h 44mYYZ-MDW
$317
6/4Tue
1 stopWestJet
7h 34mMDW-YYZ
6/17Mon
1 stopWestJet
24h 13mYYZ-MDW
$350
8/31Sat
1 stopWestJet
5h 14mMDW-YYZ
9/2Mon
1 stopWestJet
12h 21mYYZ-MDW
$355

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Recent one-way flight deals

9/20Fri
1 stopDelta
7h 43mMDW-YYC
$108
6/29Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$111
7/29Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$112
9/21Sat
1 stopDelta
9h 44mMDW-YYC
$112
8/15Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$115
6/20Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$116
6/20Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$117
6/11Tue
1 stopKLM
8h 04mMDW-YYZ
$138
8/6Tue
1 stopWestJet
5h 13mMDW-YYZ
$154
6/15Sat
1 stopWestJet
15h 27mMDW-YYZ
$162

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

5/27Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
8/13Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$333
5/27Mon
multi-stopPorter Airlines
3h 55mMDW-YUL
6/3Mon
multi-stopPorter Airlines
4h 02mYUL-MDW
$371
5/27Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
6/2Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$411
5/27Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/28Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$425
5/27Mon
multi-stopDelta
11h 03mMDW-YVR
6/1Sat
multi-stopDelta
11h 07mYVR-MDW
$453
5/26Sun
multi-stopDelta
9h 47mMDW-YYC
5/30Thu
multi-stopDelta
9h 12mYYC-MDW
$507
5/25Sat
multi-stopWestJet
25h 40mMDW-YHZ
5/27Mon
multi-stopWestJet
26h 20mYHZ-MDW
$522
5/23Thu
multi-stop
21h 00mMDW-YVR
5/31Fri
multi-stop
24h 39mYVR-MDW
$530
5/25Sat
multi-stopWestJet
7h 12mMDW-YYZ
5/29Wed
multi-stopWestJet
8h 01mYYZ-MDW
$538
5/27Mon
multi-stop
12h 22mMDW-YYC
5/29Wed
multi-stop
15h 47mYYC-MDW
$569

Search by stops

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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:

$477
$159