$134 Find Cheap Flights from Canada to Chicago Midway Airport - Compare and Save

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Cheap Flights from Canada to Midway

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Canada to Midway

Thu, Sep 10 - Thu, Sep 10
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Wed, Sep 9 - Thu, Sep 10
Porter Airlines Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Thu, Sep 10 - Fri, Sep 11
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Sat, Sep 19 - Mon, Sep 21
Porter Airlines Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Wed, Sep 23 - Thu, Sep 24
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Fri, Sep 18 - Sun, Sep 20
Porter Airlines Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Tue, Sep 8 - Tue, Sep 8
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Thu, Sep 10 - Sat, Sep 12
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$202Porter Airlines
Tue, Sep 8 - Thu, Sep 17
Air Transat Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$210Air Transat
Sun, Sep 20 - Tue, Sep 22
Multiple Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Multiple Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$216Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Midway

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

What is the cheapest flight to Chicago Midway Airport?

In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at $202 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $202 in the last 5 days.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $229. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $341 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when round-trip flights cost $287 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $388.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island Airport $201 round-trip.

Good to know

Low season

February

Cheapest flight

$134
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Toronto Island to Chicago

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at $202 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $202 in the last 5 days.

  • How far is Chicago Midway Airport from central Chicago?

    You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $267. The cheapest price found on KAYAK in the last 2 weeks cost $125 and departed from Toronto Island Airport.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    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 to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago Midway Airport?

    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 Chicago Midway Airport 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 to Chicago Midway Airport?

    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 Chicago Midway Airport 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 Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $192 or less one-way and $201 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Reviews of the top airline flying from Canada to Midway

 
Need help choosing which airline to fly with to Midway? 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 457 reviews
7.6Food
8.0Comfort
8.2Boarding
6.9Entertainment
8.6Crew
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Organization and the adjusted times but the snacks could be of a bigger portion

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

All good the seats a little tight and no I pad screen

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago