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Find cheap flights from Chicago Midway Airport to Canada from $118

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 6/8. 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
Tue 6/4
Tue 6/11

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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$258
Calgary
Calgary1 stop$308
Halifax
Halifax1 stop$406
Ottawa
Ottawa1 stop$383
Québec City
Québec City1 stop$380
Winnipeg
Winnipeg1 stop$382
St. John's
St. John's2 stops$557
Saskatoon
Saskatoon2 stops$505
Thunder Bay
Thunder Bay1 stop$482

Good to know

Low season

November

High season

July

Cheapest flight

$118
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 10826 reviews
8.2Boarding
8.6Crew
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

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!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

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!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

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

5/25Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$258
6/7Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
6/9Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$270
6/4Tue
2 stops
19h 23mMDW-YVR
6/11Tue
1 stop
9h 03mYVR-MDW
$303
5/25Sat
1 stopDelta
9h 47mMDW-YYC
5/29Wed
1 stopDelta
9h 12mYYC-MDW
$308
6/7Fri
1 stop
15h 29mMDW-YVR
6/10Mon
1 stop
31h 22mYVR-MDW
$309
5/25Sat
1 stopDelta
9h 47mMDW-YYC
5/29Wed
2 stopsDelta
8h 11mYYC-MDW
$318
7/23Tue
1 stopKLM
7h 48mMDW-YYZ
7/25Thu
1 stopKLM
3h 36mYYZ-MDW
$332
5/28Tue
1 stopWestJet
7h 59mMDW-YYZ
6/4Tue
1 stopWestJet
9h 36mYYZ-MDW
$367
5/25Sat
1 stopWestJet
5h 14mMDW-YYZ
5/26Sun
1 stopWestJet
4h 54mYYZ-MDW
$369
7/23Tue
1 stopKLM
4h 19mMDW-YUL
7/25Thu
1 stopKLM
3h 40mYUL-MDW
$387

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Recent one-way flight deals

6/8Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$118
9/7Sat
1 stop
25h 14mMDW-YVR
$120
6/18Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$120
5/31Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$121
6/25Tue
1 stop
16h 54mMDW-YYC
$126
6/18Tue
1 stop
9h 51mMDW-YYZ
$126
6/19Wed
1 stopDelta
6h 34mMDW-YYZ
$142
6/1Sat
1 stopDelta
5h 30mMDW-YUL
$145
7/10Wed
1 stopWestJet
5h 10mMDW-YYZ
$164
6/19Wed
1 stopWestJet
5h 10mMDW-YYZ
$167

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

5/9Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
5/14Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$447
5/6Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/13Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$448
5/10Fri
multi-stop
30h 36mMDW-YYZ
5/12Sun
multi-stop
7h 29mYYZ-MDW
$453
5/8Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
5/13Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$462
5/9Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
5/13Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$473
5/10Fri
multi-stop
30h 36mMDW-YYZ
5/12Sun
multi-stop
9h 36mYYZ-MDW
$515
5/10Fri
multi-stopWestJet
5h 10mMDW-YYZ
5/12Sun
multi-stopWestJet
4h 57mYYZ-MDW
$523
5/6Mon
multi-stopWestJet
24h 04mMDW-YYZ
5/13Mon
multi-stopWestJet
23h 57mYYZ-MDW
$527
5/9Thu
multi-stopDelta
8h 25mMDW-YYZ
5/12Sun
multi-stopDelta
4h 02mYYZ-MDW
$599
5/7Tue
multi-stopDelta
7h 59mMDW-YYZ
5/16Thu
multi-stopDelta
8h 21mYYZ-MDW
$641

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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
$234