C$ 139 Find Cheap Flights from Chicago Midway Airport to Canada – Compare and Save

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Best Canada Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Toronto
1h 40mNonstop
from C$ 310per person
Montreal
3h 41m2 stops
from C$ 429per person
Calgary
7h 22m2 stops
from C$ 429per person
Winnipeg
4h 17m2 stops
from C$ 477per person
Halifax
5h 43m3 stops
from C$ 507per person
Ottawa
3h 42m2 stops
from C$ 535per person
St. John's
7h 05m4 stops
from C$ 539per person
Vancouver
8h 19m4 stops
from C$ 547per person
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Booking Insights

KAYAK's insights & trends for Midway to Canada flights

Get data-powered insights and trends into flights from Midway to Canada to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Canada flight route?

The cheapest ticket to Canada from Chicago Midway Airport found in the last 5 days was to Toronto, at C$ 285 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Toronto Island Airport (YTZ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 285.

What is the cheapest time of day to fly to Canada?

The cheapest time of day to fly to Canada is generally in the morning, when round-trip flights cost C$ 418 on average. Morning departures are around 6% cheaper than evening flights, on average. The most expensive time of day to fly to Canada is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 443.

Can I save money by flying with a layover from Chicago Midway Airport to Canada?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at C$ 396 on average.

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

The cheapest month for flights from Chicago Midway Airport to Canada is January, when tickets cost C$ 283 (return) on average. On the other hand, the most expensive months are February and August, when the average cost of round-trip tickets is C$ 904 and C$ 534 respectively.

Good to know

Low season

January

Cheapest flight

C$ 139
Best time to beat the crowds (34% less expensive on average)
Most popular time to fly and prices are also 10% 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 from Chicago Midway Airport to Canada is likely to change within 7 days, so travellers 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 from Chicago Midway Airport to Canada with an airline and back 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 from Chicago Midway Airport to Canada up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 C$ 199 one-way - C$ 329 round-trip

Reviews of the top airline 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 460 reviews
8.2Boarding
7.6Food
8.6Crew
8.0Comfort
6.9Entertainment
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!

More options for your flight from Midway to Canada

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