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Cheap flights from Montreal to Chicago Midway Airport from C$ 239

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montreal to Chicago Midway Airport departing on 19/4. 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 Montreal to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Montreal to Chicago 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 Montreal to Chicago.

Cheap last-minute flights

Planning a quick getaway from Montreal to Chicago? 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, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Montreal to Chicago

Find recent round-trip train or bus tickets from Montreal to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:00 a.m. - 5:47 p.m.YUL-MDW
12h 47m1 stop
10:19 a.m. - 11:36 p.m.MDW-YUL
12h 17m1 stop
C$ 429WestJet
Find Deal
Fri, 24 Jan - Mon, 10 Feb
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:15 p.m. - 11:41 p.m.MDW-YUL
8h 26m1 stop
C$ 432WestJet
Find Deal
Sun, 15 Dec - Tue, 17 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
5:35 p.m. - 10:30 p.m.MDW-YUL
3h 55m1 stop
C$ 434Porter Airlines
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Thu, 20 Mar - Sun, 23 Mar
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
11:25 a.m. - 7:20 p.m.MDW-YUL
6h 55m1 stop
C$ 437Porter Airlines
Find Deal
Mon, 23 Dec - Sat, 28 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 438Porter Airlines
Find Deal
Thu, 27 Mar - Mon, 31 Mar
6:00 a.m. - 12:46 p.m.YUL-MDW
7h 46m1 stop
1:26 p.m. - 11:36 p.m.MDW-YUL
9h 10m1 stop
C$ 440WestJet
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Thu, 30 Jan - Wed, 5 Feb
5:35 p.m. - 11:48 a.m.YUL-MDW
19h 13m1 stop
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 538
Find Deal
Thu, 12 Dec - Mon, 16 Dec
5:35 p.m. - 11:48 a.m.YUL-MDW
19h 13m1 stop
12:05 p.m. - 6:00 p.m.MDW-YUL
4h 55m1 stop
C$ 543
Find Deal
Thu, 12 Dec - Mon, 16 Dec
12:50 p.m. - 5:01 p.m.YUL-MDW
5h 11m1 stop
5:50 p.m. - 11:11 p.m.MDW-YUL
4h 21m1 stop
C$ 550Delta
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Thu, 12 Dec - Mon, 16 Dec
7:10 a.m. - 12:49 p.m.YUL-MDW
6h 39m1 stop
5:50 p.m. - 11:11 p.m.MDW-YUL
4h 21m1 stop
C$ 571Delta
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Tue, 3 Dec - Sat, 14 Dec
12:45 p.m. - 6:00 p.m.YUL-MDW
6h 15m1 stop
C$ 239WestJet
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Sat, 19 Apr
6:50 a.m. - 11:10 a.m.YUL-MDW
5h 20m1 stop
C$ 243Porter Airlines
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Wed, 4 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
C$ 250Porter Airlines
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Thu, 24 Apr
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
C$ 263Porter Airlines
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Tue, 17 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
C$ 264Porter Airlines
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Wed, 25 Dec
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
C$ 265Porter Airlines
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Tue, 17 Dec
2:35 p.m. - 11:48 a.m.YUL-MDW
22h 13m2 stops
C$ 293
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Wed, 11 Dec
5:35 p.m. - 11:42 a.m.YUL-MDW
19h 07m2 stops
C$ 348
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Tue, 10 Dec
6:45 a.m. - 5:10 p.m.YUL-MDW
11h 25m2 stops
C$ 602Delta
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Sat, 29 Mar
6:45 a.m. - 5:10 p.m.YUL-MDW
11h 25m2 stops
C$ 649Delta
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Mon, 31 Mar
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 567WestJet
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Sun, 24 Nov - Wed, 27 Nov
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
12:55 p.m. - 6:15 p.m.MDW-YUL
4h 20m1 stop
C$ 591Porter Airlines
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Tue, 26 Nov - Sat, 30 Nov
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
12:05 p.m. - 7:20 p.m.MDW-YUL
6h 15m1 stop
C$ 600Porter Airlines
Find Deal
Mon, 25 Nov - Mon, 2 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
12:05 p.m. - 7:20 p.m.MDW-YUL
6h 15m1 stop
C$ 630Porter Airlines
Find Deal
Mon, 25 Nov - Mon, 2 Dec
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 631Porter Airlines
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Fri, 22 Nov - Fri, 29 Nov
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 637Porter Airlines
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Mon, 25 Nov - Tue, 3 Dec
7:10 a.m. - 12:49 p.m.YUL-MDW
6h 39m1 stop
1:30 p.m. - 11:11 p.m.MDW-YUL
8h 41m1 stop
C$ 728Delta
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Sat, 23 Nov - Tue, 26 Nov
5:15 p.m. - 2:01 p.m.YUL-MDW
21h 46m2 stops
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 796
Find Deal
Fri, 22 Nov - Fri, 29 Nov
12:50 p.m. - 2:01 p.m.YUL-MDW
26h 11m2 stops
11:15 a.m. - 7:25 p.m.MDW-YUL
7h 10m1 stop
C$ 1,137
Find Deal
Fri, 22 Nov - Sun, 24 Nov
12:50 p.m. - 5:02 p.m.YUL-MDW
5h 12m1 stop
9:31 a.m. - 9:08 p.m.MDW-YUL
10h 37m2 stops
C$ 1,783Delta
Find Deal
Mon, 25 Nov - Mon, 2 Dec

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
20 Mar
YUL11:50 a.m.Montreal Pierre Elliott Trudeau Intl
5h 50m
1 stop
MDW4:40 p.m.Chicago Midway
23 Mar
MDW5:35 p.m.Chicago Midway
3h 55m
1 stop
YUL10:30 p.m.Montreal Pierre Elliott Trudeau Intl
Porter Airlines
23 Dec
YUL10:45 a.m.Montreal Pierre Elliott Trudeau Intl
6h 55m
1 stop
MDW4:40 p.m.Chicago Midway
28 Dec
MDW11:25 a.m.Chicago Midway
6h 55m
1 stop
YUL7:20 p.m.Montreal Pierre Elliott Trudeau Intl
Porter Airlines
27 Mar
YUL11:50 a.m.Montreal Pierre Elliott Trudeau Intl
5h 50m
1 stop
MDW4:40 p.m.Chicago Midway
31 Mar
MDW5:35 p.m.Chicago Midway
4h 10m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl

WestJet flights from Montreal to Chicago Midway Airport

Our best WestJet deals on Montreal to Chicago Midway Airport flight tickets
WestJet
24 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
12h 47m
1 stop
MDW5:47 p.m.Chicago Midway
10 Feb
MDW10:19 a.m.Chicago Midway
12h 17m
1 stop
YUL11:36 p.m.Montreal Pierre Elliott Trudeau Intl
WestJet
15 Dec
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
13h 32m
1 stop
MDW6:32 p.m.Chicago Midway
17 Dec
MDW2:15 p.m.Chicago Midway
8h 26m
1 stop
YUL11:41 p.m.Montreal Pierre Elliott Trudeau Intl
WestJet
30 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
5 Feb
MDW1:26 p.m.Chicago Midway
9h 10m
1 stop
YUL11:36 p.m.Montreal Pierre Elliott Trudeau Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Montreal to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Montreal and Chicago Midway Airport?

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

In general, March is the cheapest month to fly from Montreal to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 367. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Montreal during the month September is also very affordable. Most momondo users find prices during this month for around C$ 373.

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

The cheapest day to depart on your flight to Chicago Midway Airport is on a Tuesday when prices can be found for as low as C$ 356. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Montreal because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 482.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Montreal to Chicago Midway Airport during this time can be as low as C$ 0. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 404.

Can stopping save me money on Montreal to Chicago Midway Airport flights?

You could potentially save up to 8% on your flight if you consider stops on a Montreal to Chicago Midway Airport flight.

When to book flights from Montreal to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montreal to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montreal to Chicago Midway Airport (YMQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal to Chicago Midway Airport

Best price found

C$ 239

Fastest flight time

4h 15m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is C$ 239. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is C$ 429.
The fastest flight from Montreal to Chicago Midway Airport takes 4h 15m
There are no direct flights from Montreal to Chicago Midway Airport. Popular non-direct route for this connection is Montreal Pierre Elliott Trudeau Intl Airport - Chicago Midway Airport.

  • How far is Montreal to Chicago Midway by plane?

    A flight from Montreal to Chicago Midway will travel around 1210.7 km. Typically, this will take 4h 15m by plane in normal conditions.

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

    Prices for flights from Montreal to Chicago Midway Airport are updated daily.

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

  • How old do you have to be to fly from Montreal 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 from Montreal to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Montreal to Chicago Midway Airport?


Best airlines flying from Montreal to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montreal to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 312Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Montreal to Chicago for you.

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

Flights from Montreal to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Montreal 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 from Montreal to Chicago.

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

Yes. momondo can track prices for Montreal to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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