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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 230

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 Pierre Elliott Trudeau Intl Airport to Chicago departing on 27/12. 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 Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 a.m. - 12:35 p.m.YUL-MDW
7h 35m1 stop
Delta Logo
1:05 p.m. - 11:54 p.m.MDW-YUL
9h 49m1 stop
C$ 327Delta
Find Deal
Sat, 4 Apr - Sun, 5 Apr
Porter Airlines Logo
10:15 a.m. - 3:20 p.m.YUL-MDW
6h 05m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 338Porter Airlines
Find Deal
Fri, 13 Mar - Sun, 15 Mar
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$ 346Porter Airlines
Find Deal
Wed, 31 Dec - Wed, 25 Feb
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.MDW-YUL
6h 45m1 stop
C$ 356Porter Airlines
Find Deal
Thu, 4 Dec - Fri, 5 Dec
Delta Logo
6:00 a.m. - 12:48 p.m.YUL-MDW
7h 48m1 stop
Delta Logo
6:00 a.m. - 4:57 p.m.MDW-YUL
9h 57m1 stop
C$ 357Delta
Find Deal
Mon, 19 Jan - Wed, 21 Jan
Delta Logo
6:00 a.m. - 12:46 p.m.YUL-MDW
7h 46m1 stop
Delta Logo
6:00 a.m. - 5:07 p.m.MDW-YUL
10h 07m1 stop
C$ 360Delta
Find Deal
Sat, 22 Nov - Sat, 2 May
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.MDW-YUL
5h 45m1 stop
C$ 366Porter Airlines
Find Deal
Wed, 3 Dec - Mon, 8 Dec
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$ 369Porter Airlines
Find Deal
Fri, 12 Dec - Fri, 19 Dec
Porter Airlines Logo
8:55 a.m. - 11:50 a.m.YUL-MDW
3h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.MDW-YUL
5h 45m1 stop
C$ 373Porter Airlines
Find Deal
Sat, 6 Dec - Thu, 11 Dec
WestJet Logo
7:10 a.m. - 1:07 p.m.YUL-MDW
6h 57m1 stop
WestJet Logo
1:50 p.m. - 11:47 p.m.MDW-YUL
8h 57m1 stop
C$ 459WestJet
Find Deal
Tue, 25 Nov - Tue, 2 Dec

Delta flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Our best Delta deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight tickets
Delta
4 Apr
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 35m
1 stop
MDW12:35 p.m.Chicago Midway
5 Apr
MDW1:05 p.m.Chicago Midway
9h 49m
1 stop
YUL11:54 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 327
Find similar
Delta
19 Jan
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 48m
1 stop
MDW12:48 p.m.Chicago Midway
21 Jan
MDW6:00 a.m.Chicago Midway
9h 57m
1 stop
YUL4:57 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 357
Find similar
Delta
22 Nov
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
2 May
MDW6:00 a.m.Chicago Midway
10h 07m
1 stop
YUL5:07 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 360
Find similar

Porter Airlines flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Our best Porter Airlines deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight tickets
Porter Airlines
13 Mar
YUL10:15 a.m.Montreal Pierre Elliott Trudeau Intl
6h 05m
1 stop
MDW3:20 p.m.Chicago Midway
15 Mar
MDW4:15 p.m.Chicago Midway
5h 30m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 338
Find similar
Porter Airlines
31 Dec
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
25 Feb
MDW11:00 a.m.Chicago Midway
4h 30m
1 stop
YUL4:30 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 346
Find similar
Porter Airlines
4 Dec
YUL11:25 a.m.Montreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 p.m.Chicago Midway
5 Dec
MDW11:00 a.m.Chicago Midway
6h 45m
1 stop
YUL6:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 356
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montreal Pierre Elliott Trudeau Intl Airport 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 30 October 2025.
Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport 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

Sat 4/4

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

Sun 5/4

1:05 p.m.-11:54 p.m.

1 stop9h 49m

C$ 327

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 13/3

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Sun 15/3

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

1 stop5h 30m

C$ 338

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 31/12

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

1 stop4h 20m

Chicago Midway

Wed 25/2

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

1 stop4h 30m

C$ 346

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/12

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

1 stop4h 55m

Chicago Midway

Fri 5/12

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 356

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 19/1

6:00 a.m.-12:48 p.m.

1 stop7h 48m

Chicago Midway

Wed 21/1

6:00 a.m.-4:57 p.m.

1 stop9h 57m

C$ 357

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 22/11

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

1 stop7h 46m

Chicago Midway

Sat 2/5

6:00 a.m.-5:07 p.m.

1 stop10h 07m

C$ 360

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/12

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

1 stop4h 20m

Chicago Midway

Mon 8/12

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

1 stop5h 45m

C$ 366

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 12/12

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

1 stop4h 20m

Chicago Midway

Fri 19/12

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

1 stop4h 30m

C$ 369

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 6/12

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Thu 11/12

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

1 stop5h 45m

C$ 373

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 25/11

7:10 a.m.-1:07 p.m.

1 stop6h 57m

Chicago Midway

Tue 2/12

1:50 p.m.-11:47 p.m.

1 stop8h 57m

C$ 459

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Montreal Pierre Elliott Trudeau Intl Airport 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, September is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 215. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Montreal Pierre Elliott Trudeau Intl Airport during the month May is also very affordable. Most momondo users find prices during this month for around C$ 370.

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 Pierre Elliott Trudeau Intl Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 515.

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 Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montreal Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (YUL to MDW) flight deals and tips

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

Direct flights

None
There are no direct flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. There are no popular flight routes from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport.
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  • How far is Montreal Pierre Elliott Trudeau Intl to Chicago Midway by plane?

    Montreal Pierre Elliott Trudeau Intl and Chicago Midway are 1195.5 km apart from one another. In terms of flight time, this usually takes a little over 3h 55m.

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

    Prices for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

Best airlines flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 199Free CancellationRating
8.0
384 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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Munster
Hammond
Merrillville

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

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

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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.

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