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Find cheap flights from Chicago Midway Airport to Canada from $110

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 6/18. 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
Mon 7/1
Mon 7/8

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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$244
Calgary
Calgary1 stop$293
Halifax
Halifax1 stop$289
Ottawa
Ottawa1 stop$381
Québec City
Québec City1 stop$430
Winnipeg
Winnipeg2 stops$429
St. John's
St. John's1 stop$557
Saskatoon
Saskatoon2 stops$723
Thunder Bay
Thunder Bay1 stop$472

Good to know

Low season

November

High season

July

Cheapest flight

$110
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway Airport to Toronto Pearson Airport

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 $125 one-way - $266 round-trip
  • Morning departure is around 33% 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 10410 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

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

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.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

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.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

6/13Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$244
6/29Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
7/6Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$245
6/17Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
6/19Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$248
6/30Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
7/4Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$249
9/9Mon
1 stop
12h 58mMDW-YVR
9/12Thu
1 stop
9h 24mYVR-MDW
$256
9/26Thu
1 stop
13h 04mMDW-YVR
9/29Sun
2 stops
12h 25mYVR-MDW
$259
8/15Thu
1 stopDelta
8h 29mMDW-YYZ
8/18Sun
1 stopDelta
7h 38mYYZ-MDW
$285
6/29Sat
1 stopDelta
4h 05mMDW-YYZ
7/9Tue
1 stopDelta
7h 09mYYZ-MDW
$317
8/28Wed
1 stopWestJet
10h 30mMDW-YYZ
9/4Wed
1 stopWestJet
7h 08mYYZ-MDW
$349
8/13Tue
1 stopWestJet
7h 10mMDW-YYZ
8/16Fri
2 stopsWestJet
17h 44mYYZ-MDW
$366

Search by stops

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Recent one-way flight deals

6/18Tue
1 stopDelta
8h 04mMDW-YYZ
$110
6/18Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$111
6/17Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$112
6/26Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$114
7/3Wed
1 stopDelta
6h 34mMDW-YYZ
$115
6/13Thu
1 stop
19h 10mMDW-YYC
$115
7/24Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$115
9/5Thu
1 stopWestJet
5h 26mMDW-YYZ
$158
8/28Wed
1 stopWestJet
5h 10mMDW-YYZ
$164
6/13Thu
nonstopFLYGTA Airlines
2h 30mMDW-YTZ
$15,413

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

6/4Tue
multi-stop
20h 26mMDW-YVR
6/11Tue
multi-stop
13h 34mYVR-MDW
$303
6/4Tue
multi-stop
20h 26mMDW-YVR
6/11Tue
multi-stop
17h 34mYVR-MDW
$314
6/5Wed
multi-stop
32h 30mMDW-YYC
6/8Sat
multi-stop
9h 30mYYC-MDW
$371
6/3Mon
multi-stop
29h 05mMDW-YVR
6/9Sun
multi-stop
30h 20mYVR-MDW
$387
6/4Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
8/4Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$404
6/4Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/26Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$409
6/5Wed
multi-stopDelta
7h 59mMDW-YYZ
6/10Mon
multi-stopDelta
8h 19mYYZ-MDW
$466
6/4Tue
multi-stopDelta
7h 34mMDW-YYZ
6/26Wed
multi-stopDelta
5h 34mYYZ-MDW
$467
6/4Tue
multi-stopWestJet
7h 34mMDW-YYZ
8/4Sun
multi-stopWestJet
16h 28mYYZ-MDW
$588
6/4Tue
multi-stopWestJet
7h 34mMDW-YYZ
6/8Sat
multi-stopWestJet
6h 59mYYZ-MDW
$594

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
$150