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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 234

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 1/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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.
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$ 260Porter Airlines
Sun, 15 Feb - Thu, 19 Feb
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$ 270Porter Airlines
Sat, 27 Dec - Mon, 23 Feb
Porter Airlines Logo
6:45 a.m. - 10:10 a.m.
YUL
-
MDW
4h 25m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.
MDW
-
YUL
5h 30m1 stop
C$ 291Porter Airlines
Fri, 27 Feb - Sun, 8 Mar
Porter Airlines Logo
12:05 p.m. - 3:20 p.m.
YUL
-
MDW
4h 15m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m1 stop
C$ 296Porter Airlines
Tue, 7 Apr - Fri, 10 Apr
Delta Logo
6:00 a.m. - 12:46 p.m.
YUL
-
MDW
7h 46m1 stop
Delta Logo
6:17 p.m. - 11:26 p.m.
MDW
-
YUL
4h 09m1 stop
C$ 297Delta
Wed, 11 Feb - Fri, 20 Feb
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$ 300Porter Airlines
Fri, 10 Apr - Mon, 13 Apr
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$ 303Porter Airlines
Fri, 10 Apr - Mon, 13 Apr
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$ 321Porter Airlines
Fri, 24 Apr - Mon, 27 Apr
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$ 328Porter Airlines
Fri, 24 Apr - Mon, 27 Apr
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$ 333Porter Airlines
Fri, 13 Feb - Mon, 16 Feb

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
11 Feb
YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 p.m.Chicago Midway
20 Feb
MDW6:17 p.m.Chicago Midway
4h 09m
1 stop
YUL11:26 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 297
Find similar
Delta
27 Jan
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
5h 59m
1 stop
MDW11:59 a.m.Chicago Midway
3 Feb
MDW12:48 p.m.Chicago Midway
10h 02m
1 stop
YUL11:50 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 359
Find similar
Delta
27 Apr
YUL12:45 p.m.Montreal Pierre Elliott Trudeau Intl
10h 00m
1 stop
MDW9:45 p.m.Chicago Midway
2 May
MDW2:00 p.m.Chicago Midway
8h 34m
1 stop
YUL11:34 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 450
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
15 Feb
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
19 Feb
MDW11:00 a.m.Chicago Midway
5h 45m
1 stop
YUL5:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 260
Find similar
Porter Airlines
27 Dec
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
23 Feb
MDW11:00 a.m.Chicago Midway
5h 45m
1 stop
YUL5:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 270
Find similar
Porter Airlines
27 Feb
YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:10 a.m.Chicago Midway
8 Mar
MDW4:15 p.m.Chicago Midway
5h 30m
1 stop
YUL10:45 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 291
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 15 December 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

Sun 15/2

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

1 stop4h 20m

Chicago Midway

Thu 19/2

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

1 stop5h 45m

C$ 260

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 27/12

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

1 stop4h 20m

Chicago Midway

Mon 23/2

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

1 stop5h 45m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 27/2

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

1 stop4h 25m

Chicago Midway

Sun 8/3

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

1 stop5h 30m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 7/4

12:05 p.m.-3:20 p.m.

1 stop4h 15m

Chicago Midway

Fri 10/4

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

1 stop4h 30m

C$ 296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/2

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

1 stop7h 46m

Chicago Midway

Fri 20/2

6:17 p.m.-11:26 p.m.

1 stop4h 09m

C$ 297

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

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

1 stop4h 55m

Chicago Midway

Mon 13/4

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

1 stop5h 30m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

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

1 stop4h 20m

Chicago Midway

Mon 13/4

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

1 stop4h 30m

C$ 303

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 24/4

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

1 stop4h 55m

Chicago Midway

Mon 27/4

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

1 stop6h 45m

C$ 321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 24/4

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

1 stop4h 20m

Chicago Midway

Mon 27/4

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

1 stop4h 30m

C$ 328

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 13/2

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

1 stop4h 55m

Chicago Midway

Mon 16/2

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

1 stop4h 30m

C$ 333

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 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$ 212. 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$ 365.

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$ 351. 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$ 507.

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$ 382. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 404.

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

Fastest flight time

4h 14m

Direct flights

None
The fastest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport takes 4h 14m
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.
Search flight deals

  • 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 4h 14m.

  • 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$ 196Free CancellationRating
8.0
399 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

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

Finding the right flight to Chicago from Montreal is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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.

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.

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Price alerts on flights to Chicago from Montreal are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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