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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 196

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 30/10. 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

Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 323Porter Airlines
Find Deal
Fri, 17 Oct - Mon, 20 Oct
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 325Porter Airlines
Find Deal
Fri, 17 Oct - Mon, 20 Oct
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 326Porter Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 327Porter Airlines
Find Deal
Tue, 21 Oct - Thu, 23 Oct
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 329Porter Airlines
Find Deal
Wed, 15 Oct - Sun, 19 Oct
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$ 333Porter Airlines
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
4:23 p.m. - 11:48 p.m.MDW-YUL
6h 25m1 stop
C$ 399Delta
Find Deal
Sun, 12 Oct - Sat, 25 Oct
Delta Logo
12:50 p.m. - 6:08 p.m.YUL-MDW
6h 18m1 stop
Delta Logo
9:32 a.m. - 3:55 p.m.MDW-YUL
5h 23m1 stop
C$ 401Delta
Find Deal
Sat, 22 Nov - Sat, 29 Nov
Delta Logo
7:00 a.m. - 4:14 p.m.YUL-MDW
10h 14m1 stop
Delta Logo
5:34 p.m. - 11:59 p.m.MDW-YUL
5h 25m1 stop
C$ 410Delta
Find Deal
Thu, 6 Nov - Mon, 10 Nov
Multiple Airlines Logo
4:45 p.m. - 11:25 p.m.YUL-MDW
7h 40m2 stops
Multiple Airlines Logo
9:35 a.m. - 8:15 a.m.MDW-YUL
21h 40m1 stop
C$ 421Multiple Airlines
Find Deal
Tue, 14 Oct - Tue, 21 Oct

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
17 Oct
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
4h 14m
1 stop
MDW4:24 p.m.Chicago Midway
20 Oct
MDW9:35 a.m.Chicago Midway
5h 25m
1 stop
YUL4:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 323
Find similar
Porter Airlines
17 Oct
YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl
4h 14m
1 stop
MDW4:24 p.m.Chicago Midway
20 Oct
MDW9:35 a.m.Chicago Midway
5h 25m
1 stop
YUL4:00 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 325
Find similar
Porter Airlines
16 Oct
YUL10:45 a.m.Montreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 p.m.Chicago Midway
19 Oct
MDW5:20 p.m.Chicago Midway
3h 55m
1 stop
YUL10:15 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 326
Find similar

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
12 Oct
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 28m
1 stop
MDW12:28 p.m.Chicago Midway
25 Oct
MDW4:23 p.m.Chicago Midway
6h 25m
1 stop
YUL11:48 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 399
Find similar
Delta
22 Nov
YUL12:50 p.m.Montreal Pierre Elliott Trudeau Intl
6h 18m
1 stop
MDW6:08 p.m.Chicago Midway
29 Nov
MDW9:32 a.m.Chicago Midway
5h 23m
1 stop
YUL3:55 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 401
Find similar
Delta
6 Nov
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 14m
1 stop
MDW4:14 p.m.Chicago Midway
10 Nov
MDW5:34 p.m.Chicago Midway
5h 25m
1 stop
YUL11:59 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 410
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 16 September 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

Fri 17/10

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

1 stop4h 14m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 323

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

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

1 stop4h 14m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 325

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 19/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 326

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 21/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Thu 23/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 327

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/10

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

1 stop4h 14m

Chicago Midway

Sun 19/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 21/11

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

1 stop4h 20m

Chicago Midway

Mon 24/11

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

1 stop4h 30m

C$ 333

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/10

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

1 stop7h 28m

Chicago Midway

Sat 25/10

4:23 p.m.-11:48 p.m.

1 stop6h 25m

C$ 399

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 22/11

12:50 p.m.-6:08 p.m.

1 stop6h 18m

Chicago Midway

Sat 29/11

9:32 a.m.-3:55 p.m.

1 stop5h 23m

C$ 401

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 6/11

7:00 a.m.-4:14 p.m.

1 stop10h 14m

Chicago Midway

Mon 10/11

5:34 p.m.-11:59 p.m.

1 stop5h 25m

C$ 410

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 14/10

4:45 p.m.-11:25 p.m.

2 stops7h 40m

Chicago Midway

Tue 21/10

9:35 a.m.-8:15 a.m.

1 stop21h 40m

C$ 421

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 typical price of a round-trip flight between Montreal Pierre Elliott Trudeau Intl Airport and Chicago Midway Airport?

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$ 298. 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$ 366.

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$ 353. 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$ 509.

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$ 383. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 405.

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$ 203Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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Hammond
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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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