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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 6/10. 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 6/7
Fri 6/14

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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$239
Calgary
Calgary1 stop$257
Halifax
Halifax1 stop$292
Ottawa
Ottawa1 stop$393
Québec City
Québec City1 stop$394
Winnipeg
Winnipeg1 stop$411
St. John's
St. John's2 stops$504
Saskatoon
Saskatoon2 stops$654
Thunder Bay
Thunder Bay1 stop$399

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 - $273 round-trip
  • Morning departure is around 12% 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 10789 reviews
7.9Comfort
8.2Boarding
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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

6/4Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/18Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$239
6/11Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/15Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$247
5/25Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
5/26Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$248
10/2Wed
1 stopDelta
7h 43mMDW-YYC
10/13Sun
1 stopDelta
5h 12mYYC-MDW
$257
6/11Tue
2 stops
11h 53mMDW-YYC
6/18Tue
1 stop
8h 03mYYC-MDW
$292
10/5Sat
1 stopDelta
9h 44mMDW-YYC
10/13Sun
1 stopDelta
5h 12mYYC-MDW
$293
6/11Tue
2 stops
11h 53mMDW-YYC
6/18Tue
1 stop
8h 03mYYC-MDW
$301
6/13Thu
1 stopWestJet
5h 14mMDW-YYZ
6/16Sun
1 stopWestJet
11h 13mYYZ-MDW
$377
8/17Sat
2 stopsWestJet
11h 45mMDW-YYZ
8/24Sat
1 stopWestJet
4h 54mYYZ-MDW
$379
7/28Sun
nonstopAPG Airlines
1h 42mMDW-YTZ
8/9Fri
nonstopAPG Airlines
1h 47mYTZ-MDW
$429

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Recent one-way flight deals

6/10Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$107
5/25Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$109
5/26Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$110
9/4Wed
2 stopsDelta
12h 17mMDW-YYC
$113
8/13Tue
1 stop
20h 48mMDW-YVR
$116
5/28Tue
1 stop
20h 26mMDW-YVR
$120
9/4Wed
1 stopDelta
9h 42mMDW-YYC
$127
7/6Sat
1 stopWestJet
15h 27mMDW-YYZ
$156
6/5Wed
1 stopWestJet
7h 04mMDW-YYZ
$160
9/24Tue
2 stopsKLM
21h 38mMDW-YHZ
$369

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

5/13Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/20Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$330
5/13Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/18Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$378
5/13Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/15Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$390
5/11Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
5/20Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$403
5/10Fri
multi-stopWestJet
6h 59mMDW-YWG
5/13Mon
multi-stopWestJet
24h 32mYWG-MDW
$437
5/10Fri
multi-stopWestJet
12h 56mMDW-YWG
5/13Mon
multi-stopWestJet
24h 32mYWG-MDW
$442
5/13Mon
multi-stop
7h 04mMDW-YYZ
5/14Tue
multi-stop
16h 16mYYZ-MDW
$493
5/11Sat
multi-stop
26h 11mMDW-YVR
5/19Sun
multi-stop
12h 50mYVR-MDW
$567
5/12Sun
multi-stopDelta
7h 59mMDW-YYZ
5/19Sun
multi-stopDelta
8h 21mYYZ-MDW
$588
5/10Fri
multi-stopDelta
7h 34mMDW-YYZ
5/13Mon
multi-stopDelta
8h 21mYYZ-MDW
$652

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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:

$292
$241