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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from $165

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 12/27. 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
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 4:30 pmMDW-YUL
4h 30m1 stop
$248Porter Airlines
Find Deal
Wed, Dec 31 - Wed, Feb 25
Porter Airlines Logo
11:25 am - 3:20 pmYUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 am - 6:45 pmMDW-YUL
6h 45m1 stop
$255Porter Airlines
Find Deal
Thu, Dec 4 - Fri, Dec 5
Delta Logo
6:00 am - 12:48 pmYUL-MDW
7h 48m1 stop
Delta Logo
6:00 am - 4:57 pmMDW-YUL
9h 57m1 stop
$256Delta
Find Deal
Mon, Jan 19 - Wed, Jan 21
Delta Logo
6:00 am - 12:46 pmYUL-MDW
7h 46m1 stop
Delta Logo
6:00 am - 5:07 pmMDW-YUL
10h 07m1 stop
$258Delta
Find Deal
Sat, Nov 22 - Sat, May 2
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$262Porter Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 8
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
$264Porter Airlines
Find Deal
Fri, Dec 12 - Fri, Dec 19
Porter Airlines Logo
8:55 am - 11:50 amYUL-MDW
3h 55m1 stop
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$267Porter Airlines
Find Deal
Sat, Dec 6 - Thu, Dec 11
Multiple Airlines Logo
7:00 am - 1:07 pmYUL-MDW
7h 07m1 stop
Multiple Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$272Multiple Airlines
Find Deal
Tue, Apr 21 - Wed, Apr 29
Multiple Airlines Logo
7:00 am - 1:07 pmYUL-MDW
7h 07m1 stop
Multiple Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
$274Multiple Airlines
Find Deal
Tue, Apr 21 - Wed, Apr 29
WestJet Logo
7:10 am - 1:07 pmYUL-MDW
6h 57m1 stop
WestJet Logo
1:50 pm - 11:47 pmMDW-YUL
8h 57m1 stop
$329WestJet
Find Deal
Tue, Nov 25 - Tue, Dec 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 31
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Feb 25
MDW11:00 amChicago Midway
4h 30m
1 stop
YUL4:30 pmMontreal Pierre Elliott Trudeau Intl
$248
Find similar
Porter Airlines
Dec 4
YUL11:25 amMontreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 pmChicago Midway
Dec 5
MDW11:00 amChicago Midway
6h 45m
1 stop
YUL6:45 pmMontreal Pierre Elliott Trudeau Intl
$255
Find similar
Porter Airlines
Dec 3
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Dec 8
MDW11:00 amChicago Midway
5h 45m
1 stop
YUL5:45 pmMontreal Pierre Elliott Trudeau Intl
$262
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
Jan 19
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 48m
1 stop
MDW12:48 pmChicago Midway
Jan 21
MDW6:00 amChicago Midway
9h 57m
1 stop
YUL4:57 pmMontreal Pierre Elliott Trudeau Intl
$256
Find similar
Delta
Nov 22
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 pmChicago Midway
May 2
MDW6:00 amChicago Midway
10h 07m
1 stop
YUL5:07 pmMontreal Pierre Elliott Trudeau Intl
$258
Find similar
Delta
Nov 29
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
10h 38m
1 stop
MDW4:38 pmChicago Midway
May 2
MDW9:30 amChicago Midway
5h 31m
1 stop
YUL4:01 pmMontreal Pierre Elliott Trudeau Intl
$297
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 832,500 searches. Data last updated October 30, 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

Wed 12/31

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Wed 2/25

11:00 am-4:30 pm

1 stop4h 30m

$248

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 12/4

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Fri 12/5

11:00 am-6:45 pm

1 stop6h 45m

$255

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 1/19

6:00 am-12:48 pm

1 stop7h 48m

Chicago Midway

Wed 1/21

6:00 am-4:57 pm

1 stop9h 57m

$256

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/22

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Sat 5/2

6:00 am-5:07 pm

1 stop10h 07m

$258

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 12/3

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 12/8

11:00 am-5:45 pm

1 stop5h 45m

$262

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 12/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Fri 12/19

11:00 am-4:30 pm

1 stop4h 30m

$264

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/6

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Thu 12/11

11:00 am-5:45 pm

1 stop5h 45m

$267

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 4/21

7:00 am-1:07 pm

1 stop7h 07m

Chicago Midway

Wed 4/29

4:15 pm-10:45 pm

1 stop5h 30m

$272

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 4/21

7:00 am-1:07 pm

1 stop7h 07m

Chicago Midway

Wed 4/29

11:00 am-5:45 pm

1 stop5h 45m

$274

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 11/25

7:10 am-1:07 pm

1 stop6h 57m

Chicago Midway

Tue 12/2

1:50 pm-11:47 pm

1 stop8h 57m

$329

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?

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
384 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

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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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