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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from $167

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 12/2. 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.
Porter Airlines Logo
10:15 am - 3:20 pmYUL-MDW
6h 05m1 stop
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$247Porter Airlines
Find Deal
Mon, Dec 8 - Mon, Dec 15
Porter Airlines Logo
11:25 am - 3:20 pmYUL-MDW
4h 55m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$248Porter Airlines
Find Deal
Sun, Mar 15 - Tue, Mar 17
Porter Airlines Logo
10:15 am - 3:20 pmYUL-MDW
6h 05m1 stop
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$249Porter Airlines
Find Deal
Mon, Dec 22 - Sun, Jan 4
Porter Airlines Logo
11:25 am - 3:20 pmYUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$251Porter Airlines
Find Deal
Sat, Dec 20 - Sun, Jan 4
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 4:30 pmMDW-YUL
4h 30m1 stop
$252Porter Airlines
Find Deal
Fri, Dec 19 - Mon, Dec 22
Delta Logo
6:00 am - 12:35 pmYUL-MDW
7h 35m1 stop
Delta Logo
2:00 pm - 11:39 pmMDW-YUL
8h 39m1 stop
$253Delta
Find Deal
Mon, Mar 9 - Fri, Mar 13
Delta Logo
6:00 am - 12:48 pmYUL-MDW
7h 48m1 stop
Delta Logo
1:28 pm - 11:12 pmMDW-YUL
8h 44m1 stop
$255Delta
Find Deal
Mon, Feb 23 - Thu, Feb 26
Porter Airlines Logo
10:15 am - 3:20 pmYUL-MDW
6h 05m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$257Porter Airlines
Find Deal
Sun, Dec 21 - Fri, Dec 26
Porter Airlines Logo
10:15 am - 3:20 pmYUL-MDW
6h 05m1 stop
Porter Airlines Logo
11:00 am - 5:15 pmMDW-YUL
5h 15m1 stop
$258Porter Airlines
Find Deal
Sat, Dec 20 - Wed, Dec 31
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$260Porter Airlines
Find Deal
Wed, Dec 24 - Fri, Jan 2

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
Dec 14
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Dec 18
MDW11:00 amChicago Midway
5h 45m
1 stop
YUL5:45 pmMontreal Pierre Elliott Trudeau Intl
$241
Find similar
Porter Airlines
Dec 8
YUL10:15 amMontreal Pierre Elliott Trudeau Intl
6h 05m
1 stop
MDW3:20 pmChicago Midway
Dec 15
MDW11:00 amChicago Midway
5h 45m
1 stop
YUL5:45 pmMontreal Pierre Elliott Trudeau Intl
$247
Find similar
Porter Airlines
Mar 15
YUL11:25 amMontreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 pmChicago Midway
Mar 19
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$248
Find similar

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
Jan 8
YUL7:30 pmMontreal Pierre Elliott Trudeau Intl
16h 04m
2 stops
MDW10:34 amChicago Midway
Jan 11
MDW11:21 amChicago Midway
11h 29m
1 stop
YUL11:50 pmMontreal Pierre Elliott Trudeau Intl
$330
Find similar
WestJet
Nov 27
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
28h 07m
2 stops
MDW9:52 amChicago Midway
Dec 1
MDW10:47 amChicago Midway
12h 12m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$408
Find similar
WestJet
Nov 26
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
27h 52m
1 stop
MDW9:52 amChicago Midway
Dec 24
MDW9:50 amChicago Midway
13h 09m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$425
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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 832,500 searches. Data last updated November 13, 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

Mon 12/8

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Mon 12/15

11:00 am-5:45 pm

1 stop5h 45m

$247

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 3/15

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Tue 3/17

4:15 pm-10:45 pm

1 stop5h 30m

$248

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 12/22

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Sun 1/4

11:00 am-5:45 pm

1 stop5h 45m

$249

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/20

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Sun 1/4

11:00 am-5:45 pm

1 stop5h 45m

$251

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 12/19

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 12/22

11:00 am-4:30 pm

1 stop4h 30m

$252

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 3/9

6:00 am-12:35 pm

1 stop7h 35m

Chicago Midway

Fri 3/13

2:00 pm-11:39 pm

1 stop8h 39m

$253

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 2/23

6:00 am-12:48 pm

1 stop7h 48m

Chicago Midway

Thu 2/26

1:28 pm-11:12 pm

1 stop8h 44m

$255

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/21

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Fri 12/26

4:15 pm-10:45 pm

1 stop5h 30m

$257

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/20

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Wed 12/31

11:00 am-5:15 pm

1 stop5h 15m

$258

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 12/24

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Fri 1/2

4:15 pm-10:45 pm

1 stop5h 30m

$260

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport, with most prices found around $154. 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 $265.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport. The lowest ticket price found for a Friday departure recently was $277. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Montreal Pierre Elliott Trudeau Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $346.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $325 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $384. Of course, these prices can vary depending on the time of year and what airport you fly to.

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?

    The distance between Montreal Pierre Elliott Trudeau Intl and Chicago Midway is about 742.9 mi. By plane, this route typically takes 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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 necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • 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 $226Free CancellationRating
8.0
389 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
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Portage
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Schererville
Valparaiso
Crown Point
Munster
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Porter
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Saint John

Why use momondo?

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 recognisable 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?

Yes. momondo allows you to filter the results for Montreal to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Montreal to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Montreal. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Montreal to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Montreal. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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