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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 232

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 18/8. 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
1 adult, Economy, 0 bags

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
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 372Porter Airlines
Sat, 12 Sep - Sat, 19 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 372Porter Airlines
Wed, 2 Sep - Tue, 8 Sep
Porter Airlines Logo
9:00 a.m. - 2:35 p.m.
YUL
-
MDW
6h 35m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 373Porter Airlines
Thu, 24 Sep - Tue, 29 Sep
Porter Airlines Logo
6:30 a.m. - 9:45 a.m.
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:10 p.m.
MDW
-
YUL
6h 45m
1 stop
C$ 373Porter Airlines
Thu, 20 Aug - Tue, 25 Aug
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
11:45 a.m. - 6:12 p.m.
MDW
-
YUL
5h 27m
1 stop
C$ 375Porter Airlines
Wed, 2 Sep - Tue, 8 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
3:20 p.m. - 9:12 p.m.
MDW
-
YUL
4h 52m
1 stop
C$ 375Porter Airlines
Tue, 8 Sep - Fri, 11 Sep
Porter Airlines Logo
6:30 a.m. - 11:00 a.m.
YUL
-
MDW
5h 30m
1 stop
Porter Airlines Logo
3:20 p.m. - 9:12 p.m.
MDW
-
YUL
4h 52m
1 stop
C$ 375Porter Airlines
Wed, 9 Sep - Fri, 11 Sep
Porter Airlines Logo
9:00 a.m. - 2:35 p.m.
YUL
-
MDW
6h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 9:12 p.m.
MDW
-
YUL
4h 52m
1 stop
C$ 375Porter Airlines
Wed, 9 Sep - Thu, 10 Sep
Delta Logo
6:00 a.m. - 12:39 p.m.
YUL
-
MDW
7h 39m
1 stop
Delta Logo
1:51 p.m. - 11:40 p.m.
MDW
-
YUL
8h 49m
1 stop
C$ 393Delta
Tue, 11 Aug - Wed, 12 Aug
Delta Logo
7:00 a.m. - 4:15 p.m.
YUL
-
MDW
10h 15m
1 stop
Delta Logo
1:25 p.m. - 11:30 p.m.
MDW
-
YUL
9h 05m
1 stop
C$ 393Delta
Wed, 12 Aug - Wed, 19 Aug

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

Our best WestJet deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight tickets
WestJet
12 Aug
YUL12:52 p.m.Montreal Pierre Elliott Trudeau Intl
6h 46m
1 stop
MDW6:38 p.m.Chicago Midway
15 Aug
MDW1:30 p.m.Chicago Midway
9h 05m
1 stop
YUL11:35 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 432
WestJet
13 Aug
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
10h 15m
1 stop
MDW4:15 p.m.Chicago Midway
17 Aug
MDW12:46 p.m.Chicago Midway
10h 06m
1 stop
YUL11:52 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 455

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
2 Sep
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 a.m.Chicago Midway
8 Sep
MDW11:45 a.m.Chicago Midway
5h 27m
1 stop
YUL6:12 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 372
Porter Airlines
20 Aug
YUL6:30 a.m.Montreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 a.m.Chicago Midway
25 Aug
MDW10:25 a.m.Chicago Midway
6h 45m
1 stop
YUL6:10 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 373
Porter Airlines
9 Sep
YUL9:00 a.m.Montreal Pierre Elliott Trudeau Intl
6h 35m
1 stop
MDW2:35 p.m.Chicago Midway
10 Sep
MDW3:20 p.m.Chicago Midway
4h 52m
1 stop
YUL9:12 p.m.Montreal Pierre Elliott Trudeau Intl
C$ 375

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 31 July 2026.
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

Cheapest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Sat 19/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 372

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Tue 8/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 372

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 24/9

9:00 a.m.-2:35 p.m.

1 stop6h 35m

Chicago Midway

Tue 29/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 373

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/8

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Tue 25/8

10:25 a.m.-6:10 p.m.

1 stop6h 45m

C$ 373

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Tue 8/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 375
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 8/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Fri 11/9

3:20 p.m.-9:12 p.m.

1 stop4h 52m

C$ 375

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Fri 11/9

3:20 p.m.-9:12 p.m.

1 stop4h 52m

C$ 375

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/9

9:00 a.m.-2:35 p.m.

1 stop6h 35m

Chicago Midway

Thu 10/9

3:20 p.m.-9:12 p.m.

1 stop4h 52m

C$ 375

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 11/8

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Wed 12/8

1:51 p.m.-11:40 p.m.

1 stop8h 49m

C$ 393

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 12/8

7:00 a.m.-4:15 p.m.

1 stop10h 15m

Chicago Midway

Wed 19/8

1:25 p.m.-11:30 p.m.

1 stop9h 05m

C$ 393

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, March 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$ 0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Montreal Pierre Elliott Trudeau Intl Airport during the month January is also very affordable. Most momondo users find prices during this month for around C$ 0.

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 10m

Direct flights

None
The fastest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport takes 4h 10m
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

Frequently asked questions about flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

  • 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 10m.

  • 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$ 245Free CancellationRating
8.0
449 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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Hammond
Munster
Valparaiso
Portage

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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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