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Cheap flights from Montreal to Chicago Midway Airport from C$ 243

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 31/3. 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.
8:55 a.m. - 12:10 p.m.YUL-MDW
4h 15m1 stop
1:05 p.m. - 6:00 p.m.MDW-YUL
3h 55m1 stop
C$ 376Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
6:50 a.m. - 12:10 p.m.YUL-MDW
6h 20m1 stop
1:05 p.m. - 7:25 p.m.MDW-YUL
5h 20m1 stop
C$ 379Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
11:15 a.m. - 4:50 p.m.MDW-YUL
4h 35m1 stop
C$ 410Porter Airlines
Find Deal
Thu, 20 Mar - Sun, 23 Mar
6:50 a.m. - 12:10 p.m.YUL-MDW
6h 20m1 stop
1:05 p.m. - 7:25 p.m.MDW-YUL
5h 20m1 stop
C$ 411Porter Airlines
Find Deal
Wed, 5 Feb - Wed, 12 Feb
6:00 a.m. - 10:36 a.m.YUL-MDW
5h 36m1 stop
6:28 p.m. - 11:25 p.m.MDW-YUL
3h 57m1 stop
C$ 553Delta
Find Deal
Sat, 11 Jan - Sun, 12 Jan
7:05 a.m. - 1:08 p.m.YUL-MDW
7h 03m1 stop
3:41 p.m. - 11:52 p.m.MDW-YUL
7h 11m1 stop
C$ 555Delta
Find Deal
Thu, 16 Jan - Sun, 19 Jan
7:30 a.m. - 1:05 p.m.YUL-MDW
6h 35m1 stop
9:20 a.m. - 11:18 p.m.MDW-YUL
12h 58m1 stop
C$ 592WestJet
Find Deal
Wed, 4 Jun - Sun, 15 Jun
7:30 a.m. - 1:05 p.m.YUL-MDW
6h 35m1 stop
1:05 p.m. - 11:43 p.m.MDW-YUL
9h 38m1 stop
C$ 611WestJet
Find Deal
Sat, 26 Apr - Tue, 29 Apr
6:15 a.m. - 8:43 p.m.YUL-MDW
15h 28m2 stops
1:05 p.m. - 6:00 p.m.MDW-YUL
3h 55m1 stop
C$ 625
Find Deal
Mon, 13 Jan - Wed, 15 Jan
6:55 a.m. - 11:10 a.m.YUL-MDW
5h 15m1 stop
10:04 p.m. - 4:35 p.m.MDW-YUL
17h 31m2 stops
C$ 691
Find Deal
Fri, 3 Jan - Mon, 6 Jan
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
C$ 243Porter Airlines
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Mon, 31 Mar
6:50 a.m. - 12:10 p.m.YUL-MDW
6h 20m1 stop
C$ 247Porter Airlines
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Mon, 3 Feb
6:50 a.m. - 12:10 p.m.YUL-MDW
6h 20m1 stop
C$ 249Porter Airlines
Find Deal
Wed, 15 Jan
6:50 a.m. - 12:10 p.m.YUL-MDW
6h 20m1 stop
C$ 260Porter Airlines
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Thu, 16 Jan
6:45 a.m. - 12:13 a.m.YUL-MDW
18h 28m3 stops
C$ 290
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Tue, 14 Jan
5:35 p.m. - 1:06 p.m.YUL-MDW
20h 31m2 stops
C$ 300
Find Deal
Sat, 18 Jan
6:00 a.m. - 12:46 p.m.YUL-MDW
7h 46m1 stop
C$ 318Delta
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Sun, 12 Jan
6:30 p.m. - 10:12 a.m.YUL-MDW
16h 42m2 stops
C$ 355WestJet
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Tue, 14 Jan
6:30 p.m. - 10:12 a.m.YUL-MDW
16h 42m2 stops
C$ 365WestJet
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Tue, 21 Jan
7:05 a.m. - 5:47 p.m.YUL-MDW
11h 42m2 stops
C$ 670Delta
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Wed, 8 Jan
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
1:05 p.m. - 6:00 p.m.MDW-YUL
3h 55m1 stop
C$ 694Porter Airlines
Find Deal
Thu, 26 Dec - Thu, 30 Jan
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 790Porter Airlines
Find Deal
Thu, 26 Dec - Wed, 1 Jan
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 5:30 p.m.MDW-YUL
5h 15m1 stop
C$ 808Porter Airlines
Find Deal
Thu, 26 Dec - Tue, 31 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 5:30 p.m.MDW-YUL
5h 15m1 stop
C$ 815Porter Airlines
Find Deal
Mon, 23 Dec - Tue, 31 Dec
6:00 a.m. - 11:08 a.m.YUL-MDW
6h 08m1 stop
5:35 p.m. - 10:30 p.m.MDW-YUL
3h 55m1 stop
C$ 987
Find Deal
Mon, 23 Dec - Sun, 5 Jan
2:35 p.m. - 5:54 p.m.YUL-MDW
28h 19m2 stops
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 1,065
Find Deal
Fri, 27 Dec - Mon, 30 Dec
7:00 a.m. - 10:06 p.m.YUL-MDW
16h 06m1 stop
4:50 p.m. - 11:43 p.m.MDW-YUL
5h 53m1 stop
C$ 1,089WestJet
Find Deal
Thu, 26 Dec - Tue, 31 Dec
12:38 p.m. - 9:23 a.m.YUL-MDW
21h 45m1 stop
11:48 a.m. - 12:30 p.m.MDW-YUL
23h 42m2 stops
C$ 1,174WestJet
Find Deal
Mon, 23 Dec - Mon, 30 Dec
6:05 a.m. - 4:24 p.m.YUL-MDW
11h 19m2 stops
4:50 p.m. - 11:43 p.m.MDW-YUL
5h 53m1 stop
C$ 1,668Delta
Find Deal
Fri, 27 Dec - Tue, 31 Dec
6:45 a.m. - 4:24 p.m.YUL-MDW
10h 39m2 stops
5:51 p.m. - 11:09 p.m.MDW-YUL
4h 18m1 stop
C$ 1,677Delta
Find Deal
Thu, 26 Dec - Tue, 31 Dec

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
11 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
5h 36m
1 stop
MDW10:36 a.m.Chicago Midway
12 Jan
MDW6:28 p.m.Chicago Midway
3h 57m
1 stop
YUL11:25 p.m.Montreal Pierre Elliott Trudeau Intl
Delta
16 Jan
YUL7:05 a.m.Montreal Pierre Elliott Trudeau Intl
7h 03m
1 stop
MDW1:08 p.m.Chicago Midway
19 Jan
MDW3:41 p.m.Chicago Midway
7h 11m
1 stop
YUL11:52 p.m.Montreal Pierre Elliott Trudeau Intl
Delta
28 Mar
YUL6:05 a.m.Montreal Pierre Elliott Trudeau Intl
9h 10m
1 stop
MDW2:15 p.m.Chicago Midway
31 Mar
MDW1:16 p.m.Chicago Midway
9h 23m
1 stop
YUL11:39 p.m.Montreal Pierre Elliott Trudeau Intl

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
13 Feb
YUL8:55 a.m.Montreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
3h 55m
1 stop
YUL6:00 p.m.Montreal Pierre Elliott Trudeau Intl
Porter Airlines
13 Feb
YUL6:50 a.m.Montreal Pierre Elliott Trudeau Intl
6h 20m
1 stop
MDW12:10 p.m.Chicago Midway
16 Feb
MDW1:05 p.m.Chicago Midway
5h 20m
1 stop
YUL7:25 p.m.Montreal Pierre Elliott Trudeau Intl
Porter Airlines
20 Mar
YUL6:50 a.m.Montreal Pierre Elliott Trudeau Intl
4h 30m
1 stop
MDW10:20 a.m.Chicago Midway
23 Mar
MDW11:15 a.m.Chicago Midway
4h 35m
1 stop
YUL4:50 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 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$ 378. 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$ 384.

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$ 367. 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$ 530.

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$ 421.

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

You could potentially save up to 19% 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$ 243

Fastest flight time

4h 05m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is C$ 243. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is C$ 376.
The fastest flight from Montreal to Chicago Midway Airport takes 4h 05m
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 05m 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$ 328Free CancellationRating
7.9
282 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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