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Flight Deals
Cheap Flights from Midway to Canada
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Midway to Canada Plane Tickets
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Canada that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Recent round-trip flight deals from Midway to Canada
Fri, Jan 22 - Fri, Jan 29
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Mon, Jan 25 - Fri, Jan 29
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Sun, Jan 24 - Fri, Jan 29
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Thu, Jan 21 - Thu, Jan 28
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Mon, Jan 25 - Thu, Jan 28
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Thu, Jan 21 - Fri, Jan 29
12:44 pm - 10:01 pmMDW Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
8:45 am - 4:53 pmYYC Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
$365Delta
Sat, Dec 12 - Sun, Dec 13
6:00 am - 1:47 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
6h 47m1 stop Atlanta Hartsfield-Jackson
6:00 am - 1:01 pmYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
8h 01m1 stop Detroit Metropolitan Wayne County
$367KLM
Thu, Nov 12 - Sun, Nov 15
9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 00m1 stop Detroit Metropolitan Wayne County
6:00 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
$395Multiple Airlines
Thu, Nov 12 - Mon, Nov 16
9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 00m1 stop Detroit Metropolitan Wayne County
9:45 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 06m1 stop Detroit Metropolitan Wayne County
$395Delta
Sat, Nov 21 - Sun, Nov 22
1:31 pm - 10:57 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
2:20 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 44m1 stop Detroit Metropolitan Wayne County
$396Air France
Recent one-way flight deals from Midway to Canada
Wed, Dec 2
12:28 pm - 1:40 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
24h 12m2 stops Atlanta Hartsfield-Jackson Orlando
$136Multiple Airlines
Thu, Dec 17
6:43 am - 11:55 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
16h 12m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$142Multiple Airlines
Thu, Dec 17
6:43 am - 11:55 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
16h 12m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$145Multiple Airlines
Wed, Dec 16
12:28 pm - 9:55 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
32h 27m2 stops Atlanta Hartsfield-Jackson Orlando
$148Multiple Airlines
Wed, Dec 16
12:28 pm - 1:40 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
24h 12m2 stops Atlanta Hartsfield-Jackson Orlando
$149Multiple Airlines
Tue, Dec 15
12:28 pm - 3:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
25h 52m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$150Multiple Airlines
Wed, Nov 18
6:08 am - 3:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
32h 12m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$154Multiple Airlines
Wed, Dec 16
10:40 am - 1:40 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
26h 00m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Orlando
$154Multiple Airlines
Mon, Nov 30
12:30 pm - 9:58 pmMDW Chicago Midway-YYC Calgary
9h 28m1 stop Minneapolis St Paul
$155Delta
Mon, Nov 30
12:30 pm - 9:58 pmMDW Chicago Midway-YYC Calgary
9h 28m1 stop Minneapolis St Paul
$155Delta
Recent last minute flight deals from Midway to Canada
Wed, Nov 4 - Mon, Nov 16
6:04 am - 12:19 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
5h 15m1 stop Atlanta Hartsfield-Jackson
9:45 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 06m1 stop Detroit Metropolitan Wayne County
$551Delta
Wed, Nov 4 - Sun, Nov 15
6:44 pm - 10:56 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
6:00 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
$551Delta
Sat, Nov 7 - Wed, Nov 18
6:44 pm - 10:56 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
12:15 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
6h 49m1 stop Detroit Metropolitan Wayne County
$551Delta
Tue, Nov 3 - Wed, Nov 18
6:04 am - 12:19 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
5h 15m1 stop Atlanta Hartsfield-Jackson
2:20 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 44m1 stop Detroit Metropolitan Wayne County
$551Delta
Tue, Nov 3 - Thu, Nov 19
6:04 am - 12:19 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
5h 15m1 stop Atlanta Hartsfield-Jackson
2:20 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 44m1 stop Detroit Metropolitan Wayne County
$551Delta
Sat, Nov 7 - Fri, Nov 20
6:44 pm - 10:56 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
12:15 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
6h 49m1 stop Detroit Metropolitan Wayne County
$551Delta
Tue, Nov 3 - Fri, Nov 20
6:04 am - 12:19 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
5h 15m1 stop Atlanta Hartsfield-Jackson
6:00 am - 9:46 amYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
$551Delta
Wed, Nov 4 - Tue, Nov 17
6:44 pm - 10:56 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
9:45 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
4h 06m1 stop Detroit Metropolitan Wayne County
$551Delta
Fri, Nov 6 - Sun, Nov 8
12:20 pm - 1:40 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
24h 20m2 stops Dallas/Fort Worth Orlando
6:30 am - 5:47 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
12h 17m2 stops Orlando Atlanta Hartsfield-Jackson
$599Multiple Airlines
Wed, Nov 4 - Tue, Nov 10
6:42 pm - 3:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
19h 38m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
7:00 am - 11:47 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
17h 47m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
$604Multiple Airlines
Booking Insights
Price, demand and travel trends for Chicago Midway Airport to Canada flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
More
What are the cheapest fares from Chicago Midway Airport to Canada right now?
Here are the cheapest round-trip fares from Chicago Midway Airport to Canada on KAYAK in the last week:
• Calgary (YYC) from $365
• Montreal Pierre Elliott Trudeau Intl (YUL) from $367
• Toronto Pearson Intl (YYZ) from $395
• Winnipeg (YWG) from $485
• Edmonton (YEG) from $631
What’s the cheapest month to fly from Chicago Midway Airport to Canada?
These monthly figures are based on KAYAK fares from the past 12 months, with extreme outliers removed so each month's typical price is accurate.
May is the cheapest time of year to fly, with average fares of $260. Prices are highest in October, when average flight costs increase to around $381.
When is the best time to book flights from Chicago Midway Airport to Canada?
Book your flights 16 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 64% compared to booking last-minute (within 2 weeks of departure).
Which airport in Canada is the cheapest to fly to from Chicago Midway Airport?
Based on KAYAK data from the past 12 months, the cheapest airports to fly into Canada are:
• Toronto Island (YTZ) (avg. price $288)
• Montreal Pierre Elliott Trudeau Intl (YUL) (avg. price $316)
• Ottawa (YOW) (avg. price $427)
What’s the cheapest day to fly from Chicago Midway Airport to Canada?
Monday tends to be the cheapest day to fly from Chicago Midway Airport to Canada, while Sunday is the most expensive. Fares run about 20% higher that day, based on the past 12 months of KAYAK data.
What's the cheapest time of day to fly from Chicago Midway Airport to Canada?
Data from the past 12 months shows it's cheapest to fly to Canada during the morning with average prices of $327. The evening is the most expensive time to fly, with average prices of $452.
What are the cheapest airlines to fly with from Chicago Midway Airport to Canada?
Fares reflect aggregated pricing data and may not include every trip type.
Looking at KAYAK data from the last 12 months, the cheapest airlines to fly with from Chicago Midway Airport to Canada are:
• Air Transat (avg. price $293)
• Porter Airlines (avg. price $302)
• Delta (avg. price $442)
• WestJet (avg. price $452)
• Qatar Airways (avg. price $465)
What's the most popular airline to fly with from Chicago Midway Airport to Canada?
Drawing on KAYAK data from the past three months, the most popular airlines to fly with from Chicago Midway Airport to Canada are:
• Porter Airlines
• Air Transat
• Delta
• WestJet
What are the most popular regions in Canada?
Ontario, Quebec and Manitoba are the most popular regions with KAYAK travelers. Together, they make up 97% of all interest in visiting Canada, based on the past three months of KAYAK data.
What are the most popular flight destinations in Canada?
Toronto, Montreal, Ottawa, Winnipeg and Thunder Bay are the most popular flight destinations in Canada, based on KAYAK data from the past 3 months. Toronto is the clear favorite, making up 86% of that interest.
What time of day has the most delays on flights from Chicago Midway Airport to Canada?
Most flight delays from Chicago Midway Airport to Canada happen in the afternoon at 50%, while there are no delays at night.
How do nonstop and one-stop fares from Chicago Midway Airport to Canada compare?
Nonstop flights cost $288 on average, while one-stop flights average $418. If you are booking a connecting flight, the cheapest layover airport is generally Detroit Metropolitan Wayne County (DTW).
Key details for Chicago Midway Airport to Canada flights
Low season | February |
|---|---|
High season | June |
Cheapest flight | $136 |
Your Chicago Midway Airport to Canada flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Chicago Midway Airport to Canada flights
Get tips on when to book, when to fly and what to know before your trip.Reviews of the top airlines flying from Midway to Canada
8.0
Porter AirlinesOverall score based on 467 reviews
8.2Boarding
8.6Crew
6.9Entertainment
7.6Food
8.0Comfort
Airline reviews
A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..
6.0 GoodHarsh, Apr 2026
A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..
The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!
Much roomer than air Canada! Great flight for the price. No complaints
As a first time flyer with Porter I was happy with the service and comfort of the airline.
Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average
I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc
The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.
There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!
Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.
Flight was delayed over 2 hours, then landed at a different airport!
No beverage/snack service without any explanation or reason. Late boarding and delayed flight.
The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.
I'm 6' 2" and even in economy plenty of leg room
Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.
THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY
The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.
The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.
Very easy to use and convenient, you can perform any action within the same portal
Okay considering we had weather delays which the Pilot notified us of immediately!
The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.
More options for your flight from Midway to Canada
Complete your trip to Canada with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Canada
Cabin classes available on flights to Canada. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Canada
Flights from all regions of Midway to Canada. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from Midway to popular regions in Canada
Flights to popular cities in Canada
Flights to Calgaryfrom $338
Flights to Edmontonfrom $692
Flights to Halifaxfrom $638
Flights to Ottawafrom $580
Flights to Québec Cityfrom $929
Flights to Saskatoonfrom $759
Flights to Thunder Bayfrom $1,909
Flights to Torontofrom $364
Flights to Victoriafrom $1,173
Flights to Winnipegfrom $485