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Cheap flights from Montreal to Chicago from C$ 198

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 departing on 19/11. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.MDW-YUL
4h 30m1 stop
C$ 325Porter Airlines
Find Deal
Thu, 6 Nov - Sun, 9 Nov
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 334Porter Airlines
Find Deal
Fri, 21 Nov - Sun, 23 Nov
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.MDW-YUL
4h 30m1 stop
C$ 338Porter Airlines
Find Deal
Thu, 20 Nov - Tue, 25 Nov
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.MDW-YUL
4h 30m1 stop
C$ 343Porter Airlines
Find Deal
Wed, 22 Oct - Mon, 27 Oct
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
2:00 p.m. - 11:39 p.m.MDW-YUL
8h 39m1 stop
C$ 401Delta
Find Deal
Thu, 23 Oct - Tue, 10 Mar
Delta Logo
6:00 a.m. - 12:46 p.m.YUL-MDW
7h 46m1 stop
Delta Logo
9:34 a.m. - 3:55 p.m.MDW-YUL
5h 21m1 stop
C$ 402Delta
Find Deal
Sat, 15 Nov - Sun, 23 Nov
Multiple Airlines Logo
5:25 p.m. - 8:32 a.m.YUL-MDW
16h 07m2 stops
Multiple Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 431Multiple Airlines
Find Deal
Sun, 16 Nov - Sun, 23 Nov
Multiple Airlines Logo
4:00 p.m. - 11:55 p.m.YUL-MDW
8h 55m2 stops
Multiple Airlines Logo
11:00 a.m. - 5:45 p.m.MDW-YUL
5h 45m1 stop
C$ 440Multiple Airlines
Find Deal
Tue, 11 Nov - Sun, 23 Nov
WestJet Logo
6:40 p.m. - 9:40 a.m.YUL-MDW
16h 00m1 stop
WestJet Logo
10:35 a.m. - 5:34 p.m.MDW-YUL
5h 59m1 stop
C$ 447WestJet
Find Deal
Thu, 23 Oct - Sun, 26 Oct
WestJet Logo
6:40 p.m. - 9:40 a.m.YUL-MDW
16h 00m1 stop
WestJet Logo
10:35 a.m. - 5:34 p.m.MDW-YUL
5h 59m1 stop
C$ 448WestJet
Find Deal
Thu, 23 Oct - Sun, 26 Oct

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
23 Oct
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 28m
1 stop
MDW12:28 p.m.Chicago Midway
10 Mar
MDW2:00 p.m.Chicago Midway
8h 39m
1 stop
YUL11:39 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 401
Find similar
Delta
15 Nov
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
23 Nov
MDW9:34 a.m.Chicago Midway
5h 21m
1 stop
YUL3:55 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 402
Find similar
Delta
21 Nov
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 38m
1 stop
MDW4:38 p.m.Chicago Midway
23 Nov
MDW6:00 a.m.Chicago Midway
10h 21m
1 stop
YUL5:21 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 452
Find similar

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
6 Nov
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
9 Nov
MDW11:00 a.m.Chicago Midway
4h 30m
1 stop
YUL4:30 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 325
Find similar
Porter Airlines
21 Nov
YUL11:25 a.m.Montreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 p.m.Chicago Midway
23 Nov
MDW4:15 p.m.Chicago Midway
5h 30m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 334
Find similar
Porter Airlines
20 Nov
YUL11:25 a.m.Montreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 p.m.Chicago Midway
25 Nov
MDW11:00 a.m.Chicago Midway
4h 30m
1 stop
YUL4:30 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 338
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montreal to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 4 October 2025.
Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 6/11

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 9/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 325

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 21/11

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Sun 23/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 334

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/11

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Tue 25/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 338

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 22/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 27/10

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 343

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 23/10

6:00 a.m.-12:28 p.m.

1 stop7h 28m

Chicago Midway

Tue 10/3

2:00 p.m.-11:39 p.m.

1 stop8h 39m

C$ 401

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 15/11

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Sun 23/11

9:34 a.m.-3:55 p.m.

1 stop5h 21m

C$ 402

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 16/11

5:25 p.m.-8:32 a.m.

2 stops16h 07m

Chicago Midway

Sun 23/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 431

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 11/11

4:00 p.m.-11:55 p.m.

2 stops8h 55m

Chicago Midway

Sun 23/11

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 440

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 23/10

6:40 p.m.-9:40 a.m.

1 stop16h 00m

Chicago Midway

Sun 26/10

10:35 a.m.-5:34 p.m.

1 stop5h 59m

C$ 447

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 23/10

6:40 p.m.-9:40 a.m.

1 stop16h 00m

Chicago Midway

Sun 26/10

10:35 a.m.-5:34 p.m.

1 stop5h 59m

C$ 448

Flights are sorted by cheapest round-trip flights first.

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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 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$ 514.

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 in the afternoon. Flights from Montreal to Chicago Midway Airport during this time can be as low as C$ 387. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 409.

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

Direct flights

None
There are no direct flights from Montreal to Chicago Midway Airport. There are no popular flight routes from Montreal to Chicago Midway Airport.
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  • 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 14m 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$ 199Free CancellationRating
7.9
372 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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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