Find cheap flights from Canada to Chicago Midway Airport from $136
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 6/1. 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.
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Flights to Midway - Travel Insights & Trends
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 day to fly to Chicago?
Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where tickets can be as cheap as $293. On the other hand, the most expensive day to fly is Monday, where prices are $479 on average.
What is the cheapest month to fly to Chicago Midway Airport?
The cheapest month for flights to Chicago Midway Airport is January, where tickets cost $209 on average for one-way flights. On the other hand, the most expensive months are June and July, where the average cost of tickets from Canada is $464 and $417 respectively. For return trips, the best month to travel is March with an average price of $221.
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 afternoon, when flights cost $244 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $318.
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 $141 one-way - $219 round-trip.
How far in advance should I book a flight to Chicago Midway Airport?
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.
Which airline offers the most flights to Chicago Midway Airport?
Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 1,444 per week, followed by Frontier with 138 flights per week.
How long is the flight to Chicago Midway Airport?
The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montreal, which takes 2h 30m, Toronto, which takes 3h 07m, Calgary, which takes 3h 27m, and Vancouver, which takes 4h 01m.
How many direct flights to Chicago Midway Airport are there each day?
There are around 246 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the morning, with 12:00 pm the most common departure time and 47% of flights departing in the morning.
How many direct flights to Chicago Midway Airport are there each week?
Each week there are around 1,721 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 16% of flights taking off on this day.
How many long-haul flights are there to Chicago Midway Airport each week?
There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Chicago Midway Airport. Instead, there are 20 short-haul flights (up to 3 hour flight duration), with the most arriving from Toronto.
How many cities have direct flights to Chicago Midway Airport?
From Canada, there are direct flights to Chicago Midway Airport from 1 city. This city is Toronto and there are 20 direct flights each week.
FAQs - booking Chicago Midway Airport flights
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Prefer to fly non-stop to Chicago Midway?
Find which airlines fly direct to Midway, which days they fly and book direct flights.
Nonstop departures
Canada to Chicago Midway
Monday
Aeromexico, Air France, Allegiant Air, +11 more
Aeromexico, Air France, +12 more
10
11
Tuesday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Wednesday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Thursday
Aeromexico, Air France, Allegiant Air, +10 more
Aeromexico, Air France, +11 more
9
10
Friday
Aeromexico, Air France, Allegiant Air, +11 more
Aeromexico, Air France, +12 more
10
11
Saturday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Sunday
Aeromexico, Air France, Allegiant Air, +10 more
Aeromexico, Air France, +11 more
9
10
Nonstop returns
Chicago Midway to Canada
Monday
Aeromexico, Air France, Allegiant Air, +11 more
Aeromexico, Air France, +12 more
10
11
Tuesday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Wednesday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Thursday
Aeromexico, Air France, Allegiant Air, +10 more
Aeromexico, Air France, +11 more
9
10
Friday
Aeromexico, Air France, Allegiant Air, +11 more
Aeromexico, Air France, +12 more
10
11
Saturday
Aeromexico, Air France, Delta, +9 more
Aeromexico, Air France, +10 more
8
9
Sunday
Aeromexico, Air France, Allegiant Air, +10 more
Aeromexico, Air France, +11 more
9
10
Top airline flying from Canada to Midway
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.
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.
Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.
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.
The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.
The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10
Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it
I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?
Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.
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Flights to Chicago Midway Airport
Destination:
Chicago Midway Airport (MDW)United States
Return flight deals:
Chicago Midway Airport - Canada
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Popular routes
The most searched flights to Chicago Midway Airport by KAYAK users.