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Cheap flights from Montreal to Chicago from $155

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 to Chicago departing on 12/12. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 12:35 pmYUL-MDW
7h 35m1 stop
Delta Logo
1:05 pm - 11:54 pmMDW-YUL
9h 49m1 stop
$214Delta
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Tue, Feb 24 - Tue, Mar 3
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
$216Porter Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 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
$254Porter Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 23
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
Thu, Nov 13 - Mon, Nov 17
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
$266Porter Airlines
Find Deal
Thu, Jan 1 - Wed, Jan 7
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
$267Porter Airlines
Find Deal
Tue, Nov 18 - Tue, Nov 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
$268Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
7:30 pm - 9:56 amYUL-MDW
15h 26m2 stops
Multiple Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$285Multiple Airlines
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Thu, Mar 12 - Thu, Mar 26
WestJet Logo
7:00 am - 1:08 pmYUL-MDW
7h 08m1 stop
WestJet Logo
3:00 pm - 11:21 pmMDW-YUL
7h 21m1 stop
$321WestJet
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Sat, Nov 1 - Sat, Nov 8
WestJet Logo
6:40 pm - 9:40 amYUL-MDW
16h 00m1 stop
WestJet Logo
10:35 am - 5:34 pmMDW-YUL
5h 59m1 stop
$326WestJet
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Fri, Oct 24 - Sun, Oct 26

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Feb 24
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 35m
1 stop
MDW12:35 pmChicago Midway
Mar 3
MDW1:05 pmChicago Midway
9h 49m
1 stop
YUL11:54 pmMontreal Pierre Elliott Trudeau Intl
$214
Find similar
Delta
Nov 21
YUL6:26 pmMontreal Pierre Elliott Trudeau Intl
6h 14m
1 stop
MDW11:40 pmChicago Midway
Nov 23
MDW12:47 pmChicago Midway
10h 12m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$288
Find similar
Delta
Nov 28
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
10h 39m
1 stop
MDW4:39 pmChicago Midway
Dec 1
MDW5:34 pmChicago Midway
5h 25m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$308
Find similar

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
Feb 9
YUL11:25 amMontreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 pmChicago Midway
Feb 15
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$216
Find similar
Porter Airlines
Nov 14
YUL11:25 amMontreal Pierre Elliott Trudeau Intl
4h 55m
1 stop
MDW3:20 pmChicago Midway
Nov 23
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$254
Find similar
Porter Airlines
Nov 13
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Nov 17
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$260
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montreal 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 6, 2025.
Use the filters below to find and compare flights from Montreal 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

Tue 2/24

6:00 am-12:35 pm

1 stop7h 35m

Chicago Midway

Tue 3/3

1:05 pm-11:54 pm

1 stop9h 49m

$214

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 2/9

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Sun 2/15

4:15 pm-10:45 pm

1 stop5h 30m

$216

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 11/14

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Sun 11/23

4:15 pm-10:45 pm

1 stop5h 30m

$254

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/13

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 11/17

4:15 pm-10:45 pm

1 stop5h 30m

$260

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 1/1

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Wed 1/7

4:15 pm-10:45 pm

1 stop5h 30m

$266

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 11/18

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Tue 11/25

11:00 am-5:45 pm

1 stop5h 45m

$267

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/6

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Sun 11/9

11:00 am-6:45 pm

1 stop6h 45m

$268

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/12

7:30 pm-9:56 am

2 stops15h 26m

Chicago Midway

Thu 3/26

4:15 pm-10:45 pm

1 stop5h 30m

$285

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/1

7:00 am-1:08 pm

1 stop7h 08m

Chicago Midway

Sat 11/8

3:00 pm-11:21 pm

1 stop7h 21m

$321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/24

6:40 pm-9:40 am

1 stop16h 00m

Chicago Midway

Sun 10/26

10:35 am-5:34 pm

1 stop5h 59m

$326

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 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 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. 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 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 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 to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montreal 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 to Chicago Midway Airport (YMQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal to Chicago Midway Airport

Direct flights

None
There are no direct flights from Montreal to Chicago Midway Airport. There are no popular flight routes from Montreal to Chicago Midway Airport.
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  • How far is Montreal to Chicago Midway by plane?

    There are 752.3 mi between Montreal and Chicago Midway. 4h 14m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Montreal to Chicago Midway Airport?

    Prices for flights from Montreal to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Montreal to Chicago Midway Airport?

  • How old do you have to be to fly from Montreal 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 to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Montreal to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montreal to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $226Free CancellationRating
8.0
375 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montreal to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Montreal to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Montreal with this policy.

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

momondo helps you find the best flight between Montreal and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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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