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Flights to Chicago Midway

C$ 177 Cheap flights to Chicago Midway Airport

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago Midway Airport departing on 24/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Canada to Chicago Midway Airport

Cheap round-trip flights

These are some of the best round-trip flight deals from Canada to Chicago Midway Airport that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Canada to Chicago Midway Airport.

Cheap last-minute flights

Planning a quick getaway from Canada to Chicago Midway Airport? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago Midway Airport, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago Midway Airport

Find recent round-trip train or bus tickets from Canada to Chicago Midway Airport.

All round-trip flight deals to Chicago Midway Airport

The cheapest plane tickets to Chicago Midway Airport found on KAYAK recently.
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 297Porter Airlines
Find Deal
Tue, 24 Dec - Tue, 31 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 298Porter Airlines
Find Deal
Fri, 6 Dec - Sun, 8 Dec
6:15 p.m. - 5:12 p.m.YVR-MDW
20h 57m2 stops
12:43 p.m. - 12:10 a.m.MDW-YVR
13h 27m1 stop
C$ 328
Find Deal
Thu, 5 Dec - Mon, 9 Dec
6:15 p.m. - 5:12 p.m.YVR-MDW
20h 57m2 stops
12:43 p.m. - 12:10 a.m.MDW-YVR
13h 27m1 stop
C$ 330
Find Deal
Thu, 5 Dec - Mon, 9 Dec
7:30 a.m. - 6:32 p.m.YYC-MDW
10h 02m1 stop
9:30 a.m. - 8:32 p.m.MDW-YYC
12h 02m2 stops
C$ 353Delta
Find Deal
Fri, 13 Dec - Sun, 15 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 353Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 355Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
7:10 a.m. - 12:49 p.m.YUL-MDW
6h 39m1 stop
3:19 p.m. - 11:59 p.m.MDW-YUL
7h 40m1 stop
C$ 360Delta
Find Deal
Tue, 12 Nov - Wed, 13 Nov
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
9:30 a.m. - 11:33 p.m.MDW-YUL
13h 03m1 stop
C$ 406WestJet
Find Deal
Tue, 19 Nov - Tue, 26 Nov
6:15 p.m. - 9:32 a.m.YYZ-MDW
16h 17m1 stop
12:43 p.m. - 11:59 p.m.MDW-YYZ
10h 16m1 stop
C$ 419WestJet
Find Deal
Mon, 18 Nov - Tue, 19 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 177Porter Airlines
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Tue, 24 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 178Porter Airlines
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Sat, 28 Dec
6:15 p.m. - 11:26 p.m.YVR-MDW
27h 11m2 stops
C$ 185
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Sun, 15 Dec
8:35 p.m. - 1:57 p.m.YVR-MDW
15h 22m2 stops
C$ 188
Find Deal
Mon, 6 Jan
6:45 a.m. - 9:38 p.m.YYC-MDW
13h 53m2 stops
C$ 211Delta
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Sat, 26 Oct
5:40 p.m. - 8:50 a.m.YVR-MDW
13h 10m2 stops
C$ 211Delta
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Mon, 18 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 214Air Transat
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Wed, 13 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 218Air Transat
Find Deal
Wed, 13 Nov
6:30 a.m. - 1:35 p.m.YYZ-MDW
8h 05m1 stop
C$ 244WestJet
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Wed, 13 Nov
12:21 p.m. - 5:54 p.m.YYZ-MDW
6h 33m1 stop
C$ 252WestJet
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Tue, 19 Nov
6:45 a.m. - 6:15 p.m.YVR-MDW
9h 30m1 stop
1:12 p.m. - 11:00 p.m.MDW-YVR
11h 48m2 stops
C$ 397Delta
Find Deal
Sat, 26 Oct - Tue, 29 Oct
6:45 a.m. - 6:29 p.m.YVR-MDW
9h 44m1 stop
1:12 p.m. - 11:00 p.m.MDW-YVR
11h 48m2 stops
C$ 435Delta
Find Deal
Tue, 22 Oct - Thu, 31 Oct
6:30 a.m. - 4:17 p.m.YHZ-MDW
11h 47m2 stops
11:15 a.m. - 10:22 p.m.MDW-YHZ
9h 07m2 stops
C$ 447Porter Airlines
Find Deal
Thu, 24 Oct - Thu, 31 Oct
6:30 a.m. - 4:17 p.m.YHZ-MDW
11h 47m2 stops
12:55 p.m. - 8:18 p.m.MDW-YHZ
5h 23m1 stop
C$ 476Porter Airlines
Find Deal
Thu, 24 Oct - Sat, 2 Nov
6:30 a.m. - 4:17 p.m.YHZ-MDW
11h 47m2 stops
11:15 a.m. - 8:43 p.m.MDW-YHZ
7h 28m1 stop
C$ 480Porter Airlines
Find Deal
Thu, 24 Oct - Thu, 31 Oct
7:30 a.m. - 6:29 p.m.YUL-MDW
11h 59m1 stop
9:38 a.m. - 11:41 p.m.MDW-YUL
13h 03m1 stop
C$ 533WestJet
Find Deal
Thu, 24 Oct - Tue, 17 Dec
7:00 a.m. - 9:38 p.m.YUL-MDW
15h 38m1 stop
2:15 p.m. - 11:41 p.m.MDW-YUL
8h 26m1 stop
C$ 564WestJet
Find Deal
Wed, 23 Oct - Fri, 13 Dec
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
6:43 p.m. - 10:13 p.m.MDW-YTZ
26h 30m2 stops
C$ 564
Find Deal
Thu, 24 Oct - Mon, 28 Oct
7:23 p.m. - 6:15 p.m.YYZ-MDW
23h 52m1 stop
6:43 p.m. - 12:25 a.m.MDW-YYZ
28h 42m1 stop
C$ 578
Find Deal
Fri, 25 Oct - Mon, 28 Oct
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:54 p.m.MDW-YTZ
1h 39mdirect
C$ 662Air Transat
Find Deal
Wed, 23 Oct - Thu, 24 Oct
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 297Porter Airlines
Find Deal
Tue, 24 Dec - Tue, 31 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 298Porter Airlines
Find Deal
Fri, 6 Dec - Sun, 8 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 301Porter Airlines
Find Deal
Sun, 15 Dec - Sat, 11 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 304Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 305Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 306Porter Airlines
Find Deal
Mon, 11 Nov - Fri, 15 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 353Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 355Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 367
Find Deal
Sun, 17 Nov - Tue, 26 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 390Air Transat
Find Deal
Tue, 24 Dec - Fri, 3 Jan

Flights to Chicago Midway Airport - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago Midway Airport to help you craft the best travel plan.

What cabin class options are available on Canada to Chicago Midway flights?

There are 1 cabin classes available to choose from on Canada to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

On average, the cheapest flights to Chicago Midway Airport are found when departing on a Wednesday. Try to avoid departing on a Monday, as this is usually the most expensive day.

What is the cheapest airline that flies from Canada to Chicago Midway?

Porter Airlines, Delta, and Air Transat are the most popular carriers operating from Canada to Chicago Midway

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

In general, when booking your flight to Chicago Midway Airport, March is the cheapest month on average.

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

Generally, when visiting Chicago Midway Airport, Evening flights represent the best value. Afternoon flights are likely to have higher prices.

What is the cheapest Canada to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Canada - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

From most locations, to find the best deals on airfare, our data shows that users booking 24 days before flying found the cheapest flight to Chicago Midway Airport.

How long does it take to fly to Chicago Midway Airport?

Flight times from Canada to Chicago Midway Airport vary, but if you’re flying out of Toronto Pearson Intl and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 1h 51m on average. Another popular route from Canada to Chicago Midway Airport is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 4h 06m. Keep in mind that layovers or delays could extend your travel time.

Cheapest flights to Chicago Midway

Find the cheapest flights to Chicago Midway from your nearest city or airport
Find Flights from Toronto Pearson Intl Airport to Chicago Midway Airport
CHEAPEST MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTFebruary36% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 339 in February
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTOctober24% more expensiveIt costs about C$ 648 for flights to Chicago Midway Airport from Toronto Pearson Intl Airport in October
MOST POPULAR MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTAugust750% more users visitedMore momondo users searched in flights to Chicago Midway Airport from Toronto Pearson Intl Airport in August than any other month

Cheap Chicago Midway Airport flight deals and tips

Summary info about Chicago Midway Airport flight prices, duration and airlines

Best One-Way Price

C$ 177

Best Round-Trip Price

C$ 297

Fastest flight time

1h 50m

Popular in

October
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 177 (Toronto Island to Chicago Midway).
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The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 297 (Toronto Island to Chicago Midway).
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The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).
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October has the highest demand for flights to Chicago, with a 6% price increase on average.
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Frequently asked questions about flying to Chicago Midway Airport

Is there an alternative airport near Chicago Midway Airport?

Finding an alternative and possibly cheaper destination airport near Chicago Midway Airport is possible. If you are planning a flight to Chicago Midway Airport, consider booking flights to Chicago O'Hare Intl Airport (26 km from Chicago city centre).

When did momondo last update prices for flights to Chicago Midway Airport?

Prices for flights to Chicago Midway Airport are updated daily.

How many operators does momondo search for flights to Chicago Midway Airport?

The number of operators available for flights to Chicago Midway Airport is 2 as of October 2024.

How old do you have to be to fly to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights to Chicago. Millions of users trust and use momondo every year so you are in good company.

Can I find flights to Chicago with flexible booking policies on momondo?

All flight searches to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Chicago.

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Chicago Midway Airport MDW

Popular Flights to Chicago Midway Airport
Popular routes according to searches in the past day on momondo

Flights from Toronto Island to MDWfrom C$ 211

Cheapest flight routes to Chicago Midway

These routes have the cheapest flights to Chicago Midway found by momondo users in Canada
DepartingDestinationBest TimeBest Price
TorontoChicago1h 47mC$ 298
MontrealChicago4h 05mC$ 323
HalifaxChicago5h 30mC$ 338
VancouverChicago8h 23mC$ 344
CalgaryChicago9h 19mC$ 353
OttawaChicago3h 40mC$ 388
KelownaChicago12h 32mC$ 388
EdmontonChicago7h 44mC$ 439
WinnipegChicago6h 01mC$ 495
VictoriaChicago12h 23mC$ 637
SaskatoonChicago11h 25mC$ 673
St. John'sChicago26h 55mC$ 740
ReginaChicago5h 57mC$ 741
Québec CityChicago8h 24mC$ 762
Grande PrairieChicago20h 26mC$ 908
LondonChicago23h 32mC$ 1,051