Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago Midway Airport to Canada from $107

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 8/13. 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
Thu 6/27
Thu 7/4

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

In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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$278
Halifax
Halifax1 stop$317
Ottawa
Ottawa1 stop$367
Québec City
Québec City1 stop$394
Winnipeg
Winnipeg2 stops$455
St. John's
St. John's2 stops$558
Saskatoon
Saskatoon1 stop$497

Good to know

Low season

November

High season

July

Cheapest flight

$107
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 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 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 11% 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 10502 reviews
7.9Comfort
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

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.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

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

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

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

6/26Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
7/3Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$245
6/13Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$246
6/14Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$249
7/21Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
7/28Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$251
7/17Wed
1 stop
11h 32mMDW-YYC
7/23Tue
1 stop
8h 50mYYC-MDW
$278
7/16Tue
1 stop
11h 47mMDW-YYC
7/23Tue
1 stop
8h 50mYYC-MDW
$279
10/1Tue
1 stopDelta
7h 43mMDW-YYC
10/6Sun
1 stopDelta
10h 15mYYC-MDW
$303
9/14Sat
1 stopDelta
9h 44mMDW-YYC
9/22Sun
1 stopDelta
10h 15mYYC-MDW
$308
8/16Fri
1 stopWestJet
7h 10mMDW-YYZ
8/17Sat
1 stopWestJet
6h 29mYYZ-MDW
$385
7/1Mon
1 stopWestJet
9h 44mMDW-YYZ
7/4Thu
1 stopWestJet
9h 21mYYZ-MDW
$390

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/13Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$107
6/18Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$111
6/17Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$112
6/9Sun
1 stop
25h 33mMDW-YYZ
$125
6/18Tue
1 stopDelta
6h 34mMDW-YYZ
$132
7/24Wed
1 stop
11h 32mMDW-YYC
$132
6/29Sat
1 stopDelta
4h 19mMDW-YUL
$134
7/24Wed
1 stopKLM
8h 29mMDW-YYZ
$147
6/25Tue
1 stopWestJet
8h 04mMDW-YYZ
$164
7/3Wed
1 stopWestJet
5h 10mMDW-YYZ
$169

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Canada

Last minute flight, train and bus deals

5/30Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
6/28Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$417
5/31Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
9/30Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$421
5/29Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
9/13Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$428
5/29Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
6/5Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$452
5/29Wed
multi-stop
11h 10mMDW-YTZ
6/5Wed
nonstop
1h 47mYTZ-MDW
$487
6/1Sat
multi-stop
19h 20mMDW-YVR
6/8Sat
multi-stop
10h 22mYVR-MDW
$519
5/29Wed
multi-stopWestJet
7h 04mMDW-YYZ
6/5Wed
multi-stopWestJet
6h 37mYYZ-MDW
$538
5/29Wed
multi-stopWestJet
5h 10mMDW-YYZ
9/13Fri
multi-stopWestJet
5h 39mYYZ-MDW
$565
5/30Thu
multi-stopDelta
8h 25mMDW-YYZ
6/28Fri
multi-stopDelta
8h 19mYYZ-MDW
$587
6/1Sat
multi-stopDelta
12h 58mMDW-YVR
6/8Sat
multi-stopDelta
8h 49mYVR-MDW
$630

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Canada Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Canada - Chicago Midway Airport

Cabin classes:

$477
$159