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Find cheap flights from Chicago Midway Airport to Canada from $81

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 7/17. 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
Sat 6/15
Sat 6/22

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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$241
Calgary
Calgary1 stop$267
Halifax
Halifax1 stop$304
Ottawa
Ottawa1 stop$386
Québec City
Québec City1 stop$372
Winnipeg
Winnipeg1 stop$323
St. John's
St. John's2 stops$554
Saskatoon
Saskatoon1 stop$606
Thunder Bay
Thunder Bay1 stop$436

Good to know

Low season

November

High season

July

Cheapest flight

$81
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 Vancouver

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 $138 one-way - $270 round-trip
  • Morning departure is around 10% 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 10673 reviews
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
7.9Comfort
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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

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

7/17Wed
1 stop
29h 20mMDW-YVR
8/24Sat
1 stop
10h 27mYVR-MDW
$234
6/1Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
6/14Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$241
5/28Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/14Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$242
6/13Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
6/19Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$245
6/29Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
7/7Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$248
9/7Sat
1 stopDelta
9h 42mMDW-YYC
9/14Sat
1 stopDelta
10h 15mYYC-MDW
$267
6/6Thu
1 stopDelta
8h 25mMDW-YYZ
6/10Mon
1 stopDelta
8h 19mYYZ-MDW
$287
7/16Tue
1 stopKLM
4h 08mMDW-YYZ
7/23Tue
1 stopKLM
5h 34mYYZ-MDW
$312
5/29Wed
1 stopWestJet
7h 34mMDW-YYZ
6/5Wed
1 stopWestJet
4h 57mYYZ-MDW
$349
5/29Wed
1 stopWestJet
6h 18mMDW-YUL
6/1Sat
1 stopWestJet
11h 41mYUL-MDW
$358

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Recent one-way flight deals

7/17Wed
1 stop
29h 20mMDW-YVR
$81
8/7Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$111
9/25Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$112
7/11Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$116
6/11Tue
1 stopDelta
6h 34mMDW-YYZ
$132
7/27Sat
1 stopDelta
4h 16mMDW-YUL
$134
9/10Tue
1 stopKLM
8h 01mMDW-YYZ
$147
6/5Wed
1 stopWestJet
5h 10mMDW-YYZ
$155
8/10Sat
1 stopWestJet
5h 42mMDW-YYZ
$158
5/28Tue
1 stopKLM
7h 59mMDW-YYZ
$166

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

5/21Tue
multi-stopPorter Airlines
5h 55mMDW-YUL
5/28Tue
multi-stopPorter Airlines
6h 32mYUL-MDW
$374
5/21Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
5/29Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$394
5/21Tue
nonstop
1h 42mMDW-YTZ
5/29Wed
multi-stop
6h 50mYTZ-MDW
$403
5/18Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
5/29Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$441
5/18Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
5/26Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$453
5/18Sat
multi-stop
22h 12mMDW-YVR
5/25Sat
multi-stop
10h 11mYVR-MDW
$579
5/19Sun
multi-stopWestJet
7h 34mMDW-YYZ
5/22Wed
multi-stopWestJet
8h 01mYYZ-MDW
$581
5/21Tue
multi-stopDelta
8h 25mMDW-YYZ
5/29Wed
multi-stopDelta
4h 02mYYZ-MDW
$582
5/19Sun
multi-stopWestJet
12h 28mMDW-YYZ
5/21Tue
multi-stopWestJet
6h 37mYYZ-MDW
$588
5/18Sat
multi-stopDelta
8h 50mMDW-YVR
5/21Tue
multi-stopDelta
9h 17mYVR-MDW
$604

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
$232