$167 Find Cheap Flights from Canada to Chicago Midway Airport - Compare and Save
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 10/21. 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.
Flight Deals
Cheap Flights from Canada to Midway
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Canada to Midway 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 Canada to Midway
Thu, Oct 22 - Fri, Oct 23
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$274Porter Airlines
Wed, Oct 21 - Sat, Oct 24
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$287Porter Airlines
Mon, Oct 19 - Wed, Oct 21
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$288Porter Airlines
Fri, Oct 23 - Fri, Oct 23
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$289Porter Airlines
Wed, Oct 21 - Thu, Oct 22
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$290Porter Airlines
Tue, Oct 13 - Tue, Oct 20
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$293Porter Airlines
Thu, Jan 28 - Mon, Feb 1
8:45 am - 3:50 pmYYC Calgary-MDW Chicago Midway
7h 05m1 stop Minneapolis St Paul
1:00 pm - 1:13 amMDW Chicago Midway-YYC Calgary
12h 13m2 stops Detroit Metropolitan Wayne County Salt Lake City
$298Delta
Wed, Jan 27 - Sun, Jan 31
8:45 am - 5:37 pmYYC Calgary-MDW Chicago Midway
8h 52m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
1:00 pm - 10:54 pmMDW Chicago Midway-YYC Calgary
9h 54m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$298Delta
Wed, Jan 27 - Sun, Jan 31
8:45 am - 3:50 pmYYC Calgary-MDW Chicago Midway
7h 05m1 stop Minneapolis St Paul
9:30 am - 10:54 pmMDW Chicago Midway-YYC Calgary
13h 24m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$298Delta
Fri, Oct 16 - Sun, Oct 18
6:30 am - 11:00 amYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
3:20 pm - 9:12 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$307Porter Airlines
Recent one-way flight deals from Canada to Midway
Wed, Oct 21
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$167Porter Airlines
Tue, Oct 20
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$168Porter Airlines
Fri, Oct 23
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$172Porter Airlines
Thu, Oct 22
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$176Porter Airlines
Fri, Jan 15
8:45 am - 3:50 pmYYC Calgary-MDW Chicago Midway
7h 05m1 stop Minneapolis St Paul
$177Delta
Fri, Jan 15
8:45 am - 5:37 pmYYC Calgary-MDW Chicago Midway
8h 52m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
$177Delta
Mon, Oct 19
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$177Porter Airlines
Sat, Nov 21
8:45 am - 3:39 pmYYC Calgary-MDW Chicago Midway
6h 54m1 stop Minneapolis St Paul
$177Delta
Tue, Nov 3
8:45 am - 9:33 pmYYC Calgary-MDW Chicago Midway
12h 48m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$177Delta
Tue, Oct 20
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
$181Porter Airlines
Recent last minute flight deals from Canada to Midway
Sat, Oct 3 - Mon, Oct 5
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$288Porter Airlines
Wed, Sep 30 - Sat, Oct 3
9:00 am - 2:35 pmYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
11:45 am - 6:12 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$327Porter Airlines
Thu, Oct 1 - Sat, Oct 3
9:00 am - 2:35 pmYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
11:45 am - 6:12 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$331Porter Airlines
Thu, Oct 1 - Thu, Oct 1
6:30 am - 11:00 amYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
3:20 pm - 9:12 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$345Porter Airlines
Wed, Sep 30 - Wed, Oct 7
6:35 am - 1:20 pmYYC Calgary-MDW Chicago Midway
5h 45m1 stop Minneapolis St Paul
12:27 pm - 8:40 pmMDW Chicago Midway-YYC Calgary
9h 13m1 stop Minneapolis St Paul
$359Delta
Wed, Sep 30 - Wed, Oct 7
6:35 am - 1:20 pmYYC Calgary-MDW Chicago Midway
5h 45m1 stop Minneapolis St Paul
9:29 am - 8:40 pmMDW Chicago Midway-YYC Calgary
12h 11m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$359Delta
Wed, Sep 30 - Tue, Oct 6
6:35 am - 1:20 pmYYC Calgary-MDW Chicago Midway
5h 45m1 stop Minneapolis St Paul
12:27 pm - 8:40 pmMDW Chicago Midway-YYC Calgary
9h 13m1 stop Minneapolis St Paul
$359Delta
Wed, Sep 30 - Mon, Oct 5
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$362Porter Airlines
Thu, Oct 1 - Fri, Oct 2
6:30 am - 2:35 pmYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
9h 05m1 stop Toronto Island
11:45 am - 6:12 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$368Porter Airlines
Mon, Oct 5 - Tue, Oct 13
12:08 pm - 6:33 pmYYZ Toronto Pearson Intl-MDW Chicago Midway
7h 25m1 stop Detroit Metropolitan Wayne County
9:29 am - 5:19 pmMDW Chicago Midway-YYZ Toronto Pearson Intl
6h 50m1 stop Detroit Metropolitan Wayne County
$373Delta
Recent direct flight deals from Canada to Midway
Thu, Oct 22 - Fri, Oct 23
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$274Porter Airlines
Wed, Oct 21 - Sat, Oct 24
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$287Porter Airlines
Mon, Oct 19 - Wed, Oct 21
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$288Porter Airlines
Fri, Oct 23 - Fri, Oct 23
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$289Porter Airlines
Wed, Oct 21 - Thu, Oct 22
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$290Porter Airlines
Tue, Oct 13 - Tue, Oct 20
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$293Porter Airlines
Mon, Oct 19 - Thu, Oct 22
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$308Porter Airlines
Sat, Oct 17 - Tue, Oct 20
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$310Porter Airlines
Thu, Oct 15 - Sun, Oct 18
1:45 pm - 2:35 pmYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
11:45 am - 2:25 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$398Air Transat
Thu, Oct 15 - Sun, Oct 18
10:10 am - 11:00 amYTZ Toronto Island-MDW Chicago Midway
1h 50mnonstop
3:20 pm - 6:00 pmMDW Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$416Air Transat
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.
Prices
More
What is the cheapest flight to Chicago Midway Airport?
These are the best round-trip prices found by users searching on KAYAK in the last 5 days.In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at $274 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $274 in the last 5 days.
What is the cheapest day to fly to Chicago?
The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.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 $350 on average.
What is the cheapest time of day to fly to Chicago Midway Airport?
The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $292 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 $445.
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 $193 round-trip.
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 Toronto, which takes 2h 01m, Calgary, which takes 2h 20m, Montreal, which takes 2h 41m, and Vancouver, which takes 3h 09m.
How many direct flights to Chicago Midway Airport are there each day?
There are around 346 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the morning, with 41% of flights departing in the morning.
How many direct flights to Chicago Midway Airport are there each week?
Each week there are around 2,420 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 20% 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 28 short-haul flights (up to 3 hour flight duration), with the most arriving from Toronto.
Good to know
Low season | February |
|---|---|
High season | May |
Cheapest flight | $167 |
FAQs - booking Chicago Midway Airport flights
Top tips for finding cheap flights to Chicago Midway Airport
Traveling to a place near Midway?
Book flights to Midway if you plan to visit one of these locationsMerrillville
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith
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Cabin class types available on flights to Midway
Cabin classes available on flights to Midway. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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Flights from domestic origins to Midway
Flights from all regions of Canada to Midway. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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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.
Popular routes to Midway
The most searched for flights to Midway from KAYAK users over the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.