$146 Find Cheap Flights from Chicago Midway Airport to Canada - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 19% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Toronto
1h 40mNonstop
from $348per person
Montreal
3h 41m2 stops
from $352per person
Calgary
7h 38m2 stops
from $370per person
Winnipeg
4h 12m2 stops
from $419per person
Vancouver
9h 06m3 stops
from $506per person
Ottawa
5h 07m2 stops
from $543per person
Edmonton
5h 28m2 stops
from $544per person
Halifax
7h 24m4 stops
from $629per person
Explore the map
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.

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:

• Toronto Pearson Intl (YYZ) from $348
• Montreal Pierre Elliott Trudeau Intl (YUL) from $352
• Calgary (YYC) from $405
• Winnipeg (YWG) from $419
• Vancouver Intl (YVR) from $475

What’s the cheapest month to fly from Chicago Midway Airport to Canada?

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) from $288
• Montreal Pierre Elliott Trudeau Intl (YUL) from $316
• Ottawa (YOW) from $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.

Key details for Chicago Midway Airport to Canada flights

Low season

February

Cheapest flight

$146
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Chicago Midway Airport to Toronto Pearson Intl Airport

Your Chicago Midway Airport to Canada flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to Canada?

    Fares from Chicago Midway Airport to Canada are around their usual level right now. A round-trip under $241 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Chicago Midway Airport to Canada?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to Canada have ranged from $241 to $446.

  • What are the main airports serving Canada?

    Canada has 12 airports. The three busiest are Toronto Island (YTZ) (89% of arrivals), Ottawa (YOW) (3%) and Montreal Pierre Elliott Trudeau Intl (YUL) (2%).

  • What airlines fly nonstop from Chicago Midway Airport to Canada?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to Canada: Porter Airlines.

  • Where in Canada can I fly nonstop from Chicago Midway Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Chicago Midway Airport to Toronto.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to Canada?

    No, nonstop flights from Chicago Midway Airport to Canada are typically the cheaper option, averaging $288 over the past 12 months.

  • How long is a flight from Chicago Midway Airport to Canada?

    Flights from Chicago Midway Airport to Canada take 1h 40m on average.

  • How often are flights from Chicago Midway Airport to Canada delayed and what's the average delay?

    40% of flights on this route are delayed by at least 15 minutes. The average delay is 1h 18m.

  • Which cabin classes are available on flights from Chicago Midway Airport to Canada?

    On flights from Chicago Midway Airport to Canada you can book Economy Class, Premium Economy Class or First Class.

  • What are some popular landmarks in Canada?

    KAYAK travelers' favorite landmarks in Canada include:

    • Rogers Centre
    • BC Place Vancouver
    • Union Station
    • Scotiabank Arena

  • What are the earliest and latest flights from Chicago Midway Airport to Canada?

    The earliest nonstop flight from Chicago Midway Airport to Canada departs at 11:45 am and the latest departs at 3:20 pm. Nonstop flights take about 1h 40m.

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.
  • If you can plan ahead, the sweet spot for booking your flight is 16 weeks before your trip. KAYAK data shows fares in this window are around 64% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for May when flights are typically cheapest and avoid October when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Sunday cost about 20% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Toronto Island (YTZ) is the cheapest airport to fly into from Chicago Midway Airport. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Toronto, which is the most popular destination in Canada. From there, it's easy to continue on to other popular destinations such as Niagara Falls, Vancouver and Montreal.
  • Whether you're trying to save time or money, the Chicago Midway Airport to Canada nonstop route is usually your best option.

Reviews of the 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
Porter AirlinesOverall score based on 468 reviews
8.6Crew
7.0Entertainment
8.0Comfort
8.2Boarding
7.6Food
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
Read more Porter Airlines 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..

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!

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.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

More options for your flight from Midway to Canada

Complete your trip to Canada with a hotel stay or car rental