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Find cheap flights from Chicago Midway Airport to Canada from $89

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 9/23. 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 7/11
Thu 7/18

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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$237
Calgary
Calgary1 stop$238
Halifax
Halifax1 stop$263
Ottawa
Ottawa1 stop$378
Québec City
Québec City1 stop$401
Winnipeg
Winnipeg2 stops$646
St. John's
St. John's1 stop$476
Saskatoon
Saskatoon1 stop$615

Good to know

Low season

November

High season

July

Cheapest flight

$89
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 1% 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 $122 one-way - $252 round-trip
  • Morning departure is around 17% 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 10277 reviews
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
8.2Boarding
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

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

9/21Sat
1 stop
15h 36mMDW-YVR
9/25Wed
1 stop
9h 24mYVR-MDW
$235
7/8Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
7/15Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$237
7/19Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
7/21Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
$238
7/2Tue
1 stop
27h 41mMDW-YYC
7/9Tue
1 stop
8h 50mYYC-MDW
$238
9/21Sat
2 stops
14h 03mMDW-YVR
9/25Wed
1 stop
9h 24mYVR-MDW
$238
7/10Wed
1 stopDelta
8h 16mMDW-YYZ
7/17Wed
1 stopDelta
7h 09mYYZ-MDW
$306
8/16Fri
1 stopDelta
7h 46mMDW-YUL
8/21Wed
1 stopDelta
3h 38mYUL-MDW
$315
6/25Tue
1 stopWestJet
5h 10mMDW-YYZ
7/2Tue
1 stopWestJet
24h 07mYYZ-MDW
$358
8/16Fri
1 stopWestJet
7h 48mMDW-YYZ
8/24Sat
1 stopWestJet
4h 59mYYZ-MDW
$376
7/5Fri
1 stopAir Transat
3h 39mMDW-YOW
7/7Sun
1 stopAir Transat
6h 32mYOW-MDW
$394

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Recent one-way flight deals

9/23Mon
1 stop
22h 31mMDW-YVR
$89
9/10Tue
1 stop
12h 58mMDW-YVR
$95
7/22Mon
1 stopPorter Airlines
5h 30mMDW-YUL
$102
7/7Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$103
6/29Sat
1 stopDelta
6h 40mMDW-YYZ
$126
7/8Mon
1 stopDelta
7h 25mMDW-YUL
$128
8/17Sat
1 stopWestJet
5h 10mMDW-YYZ
$159
8/27Tue
2 stopsWestJet
23h 08mMDW-YHZ
$161
8/18Sun
nonstopAir Transat
1h 42mMDW-YTZ
$269
9/2Mon
nonstopAir Transat
1h 42mMDW-YTZ
$357

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Last minute flights from Midway to Canada

Last minute flight, train and bus deals

6/15Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
6/25Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$330
6/14Fri
multi-stop
26h 01mMDW-YYC
6/16Sun
multi-stop
24h 00mYYC-MDW
$377
6/15Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$388
6/13Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
7/6Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$430
6/13Thu
multi-stopWestJet
22h 25mMDW-YYZ
7/6Sat
multi-stopWestJet
16h 31mYYZ-MDW
$528
6/13Thu
multi-stopWestJet
14h 59mMDW-YYZ
6/17Mon
multi-stopWestJet
24h 13mYYZ-MDW
$551
6/13Thu
multi-stopDelta
11h 11mMDW-YVR
6/15Sat
multi-stopDelta
10h 15mYVR-MDW
$561
6/13Thu
multi-stopDelta
11h 11mMDW-YVR
6/15Sat
multi-stopDelta
8h 49mYVR-MDW
$566
6/14Fri
multi-stop
15h 19mMDW-YYZ
6/15Sat
multi-stop
23h 50mYYZ-MDW
$569
6/13Thu
multi-stopAir Transat
4h 04mMDW-YOW
6/28Fri
multi-stopAir Transat
5h 27mYOW-MDW
$639

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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:

$404
$192