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Find cheap flights from Chicago Midway Airport to Canada from $98

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 4/22. 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
sam. 4/27
sam. 5/4

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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$227
Calgary
Calgary2 stops$312
Halifax
Halifax1 stop$335
Ottawa
Ottawa1 stop$276
Québec City
Québec City1 stop$395
Winnipeg
Winnipeg1 stop$343
St. John's
St. John's1 stop$562
Saskatoon
Saskatoon1 stop$520
Thunder Bay
Thunder Bay1 stop$412

Good to know

Low season

January

High season

November

Cheapest flight

$98
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 $131 one-way - $242 round-trip
  • Morning departure is around 56% 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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
82boarding
75food
79comfort
80entertainment
81overall
86crew
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

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.

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

New jet. Lots of leg room. On time departure. Early arrival. Reasonable airfare. Excellent online experience.

I had checked in online the day before but was instructed to collect our boarding passes when we arrived. I am not completely comfortable using the automated Kiosks and always enjoy the nostalgia of speaking with someone when checking in for a flight. Upon doing so however, we were immediately asked,"did you check in online already?" To which I replied, "yes, but we were asked to retrieve our boarding passes upon arrival." She then said, "that's what those machines over there are for. We really encourage people to use those." That unfortunately sparked a series of shortness and overall poor behavior in my opinion from the woman who checked us in. I understand it was early in the morning but I am always excited to experience flying and that interaction has unfortunately left a bitter taste in my mouth to the point I will forever now hesitate to book with Porter again. Thank you for taking the time to read this. Cheers, JD

Everything was fantastic, by far the best airline experience in Canada 🇨🇦!

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

5/2jeu.
nonstopPorter Airlines
1h 42mMDW-YTZ
5/5dim.
nonstopPorter Airlines
1h 47mYTZ-MDW
$227
6/14ven.
nonstopPorter Airlines
1h 42mMDW-YTZ
6/16dim.
nonstopPorter Airlines
1h 47mYTZ-MDW
$231
4/24mer.
nonstopPorter Airlines
1h 42mMDW-YTZ
5/1mer.
nonstopPorter Airlines
1h 47mYTZ-MDW
$232
4/18jeu.
1 stopKLM
8h 21mMDW-YYZ
4/21dim.
1 stopKLM
3h 35mYYZ-MDW
$281
4/18jeu.
1 stopDelta
8h 42mMDW-YUL
4/21dim.
1 stopDelta
6h 35mYUL-MDW
$287
4/17mer.
1 stopDelta
5h 10mMDW-YYZ
4/21dim.
1 stopDelta
3h 35mYYZ-MDW
$293
4/25jeu.
1 stop
18h 46mMDW-YVR
5/2jeu.
2 stops
14h 09mYVR-MDW
$297
4/17mer.
nonstop
1h 42mMDW-YTZ
4/24mer.
1 stop
8h 03mYTZ-MDW
$306
5/11sam.
1 stopWestJet
5h 31mMDW-YUL
5/12dim.
1 stopWestJet
6h 30mYUL-MDW
$357
5/7mar.
1 stopWestJet
12h 28mMDW-YYZ
5/14mar.
1 stopWestJet
9h 36mYYZ-MDW
$366

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Recent one-way flight deals

4/22lun.
nonstopPorter Airlines
1h 42mMDW-YTZ
$98
5/6lun.
1 stopPorter Airlines
4h 45mMDW-YUL
$99
5/14mar.
1 stopDelta
7h 12mMDW-YUL
$115
5/6lun.
1 stopDelta
8h 42mMDW-YUL
$121
4/22lun.
1 stop
25h 11mMDW-YYC
$130
4/9mar.
2 stops
26h 13mMDW-YYZ
$141
5/6lun.
2 stopsWestJet
11h 45mMDW-YYZ
$166
6/1sam.
1 stopWestJet
5h 14mMDW-YYZ
$168
8/1jeu.
1 stopUndisclosed Carrier
10h 48mMDW-YYZ
$186
5/7mar.
2 stopsUndisclosed Carrier
10h 53mMDW-YHZ
$225

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

4/1lun.
nonstopPorter Airlines
1h 42mMDW-YTZ
4/13sam.
nonstopPorter Airlines
1h 47mYTZ-MDW
$440
3/31dim.
nonstopPorter Airlines
1h 42mMDW-YTZ
4/5ven.
nonstopPorter Airlines
1h 47mYTZ-MDW
$463
4/1lun.
nonstopPorter Airlines
1h 42mMDW-YTZ
4/8lun.
nonstopPorter Airlines
1h 47mYTZ-MDW
$477
4/2mar.
multi-stop
17h 56mMDW-YUL
4/8lun.
multi-stop
6h 32mYUL-MDW
$484
4/2mar.
multi-stop
17h 56mMDW-YUL
4/7dim.
multi-stop
6h 32mYUL-MDW
$490
4/2mar.
multi-stop
26h 35mMDW-YUL
4/8lun.
multi-stop
6h 32mYUL-MDW
$496
3/31dim.
multi-stopDelta
5h 51mMDW-YYZ
4/5ven.
multi-stopDelta
5h 01mYYZ-MDW
$573
4/1lun.
multi-stopWestJet
5h 04mMDW-YYZ
4/5ven.
multi-stopWestJet
6h 44mYYZ-MDW
$584
3/30sam.
multi-stopDelta
5h 51mMDW-YYZ
4/7dim.
multi-stopDelta
5h 49mYYZ-MDW
$585
3/30sam.
multi-stopWestJet
15h 41mMDW-YYZ
3/31dim.
multi-stopWestJet
11h 38mYYZ-MDW
$587

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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:

$421
$224