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Cheap flights from Montreal to Chicago from $162

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 5/20. 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.
Porter Airlines Logo
10:15 am - 3:20 pmYUL-MDW
6h 05m1 stop
Porter Airlines Logo
12:45 pm - 6:45 pmMDW-YUL
5h 00m1 stop
$194Porter Airlines
Find Deal
Tue, Apr 14 - Sat, Apr 18
Porter Airlines Logo
6:45 am - 10:10 amYUL-MDW
4h 25m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$195Porter Airlines
Find Deal
Fri, Feb 27 - Sun, Mar 8
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 6:45 pmMDW-YUL
6h 45m1 stop
$196Porter Airlines
Find Deal
Sat, Dec 27 - Mon, Feb 23
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
$199Porter Airlines
Find Deal
Wed, Mar 18 - Mon, Mar 23
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 6:45 pmMDW-YUL
6h 45m1 stop
$200Porter Airlines
Find Deal
Mon, Dec 22 - Tue, Dec 30
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
12:45 pm - 6:45 pmMDW-YUL
5h 00m1 stop
$201Porter Airlines
Find Deal
Thu, Mar 5 - Sat, Mar 7
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
$203Porter Airlines
Find Deal
Wed, Feb 18 - Sun, Feb 22
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
$205Porter Airlines
Find Deal
Fri, Feb 27 - Sun, Mar 8
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
$210Porter Airlines
Find Deal
Sun, Apr 12 - Mon, Apr 20
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
Porter Airlines Logo
11:00 am - 6:45 pmMDW-YUL
6h 45m1 stop
$211Porter Airlines
Find Deal
Sat, Dec 27 - Mon, Feb 23

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
Apr 14
YUL10:15 amMontreal Pierre Elliott Trudeau Intl
6h 05m
1 stop
MDW3:20 pmChicago Midway
Apr 18
MDW12:45 pmChicago Midway
5h 00m
1 stop
YUL6:45 pmMontreal Pierre Elliott Trudeau Intl
$194
Find similar
Porter Airlines
Feb 27
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:10 amChicago Midway
Mar 8
MDW4:15 pmChicago Midway
5h 30m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$195
Find similar
Porter Airlines
Dec 27
YUL6:45 amMontreal Pierre Elliott Trudeau Intl
4h 20m
1 stop
MDW10:05 amChicago Midway
Feb 23
MDW11:00 amChicago Midway
6h 45m
1 stop
YUL6:45 pmMontreal Pierre Elliott Trudeau Intl
$196
Find similar

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Jan 14
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 48m
1 stop
MDW12:48 pmChicago Midway
Jan 21
MDW10:46 amChicago Midway
5h 09m
1 stop
YUL4:55 pmMontreal Pierre Elliott Trudeau Intl
$221
Find similar
Delta
Mar 2
YUL12:52 pmMontreal Pierre Elliott Trudeau Intl
5h 45m
1 stop
MDW5:37 pmChicago Midway
Mar 4
MDW6:00 amChicago Midway
9h 53m
1 stop
YUL4:53 pmMontreal Pierre Elliott Trudeau Intl
$222
Find similar
Delta
Dec 14
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 34m
1 stop
MDW12:34 pmChicago Midway
Dec 15
MDW12:50 pmChicago Midway
10h 09m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$253
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 December 2, 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 4/14

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Sat 4/18

12:45 pm-6:45 pm

1 stop5h 00m

$194

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/27

6:45 am-10:10 am

1 stop4h 25m

Chicago Midway

Sun 3/8

4:15 pm-10:45 pm

1 stop5h 30m

$195

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/27

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 2/23

11:00 am-6:45 pm

1 stop6h 45m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/18

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Mon 3/23

4:15 pm-10:45 pm

1 stop5h 30m

$199

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 12/22

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Tue 12/30

11:00 am-6:45 pm

1 stop6h 45m

$200

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/5

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sat 3/7

12:45 pm-6:45 pm

1 stop5h 00m

$201

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/18

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 2/22

4:15 pm-10:45 pm

1 stop5h 30m

$203

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/27

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 3/8

4:15 pm-10:45 pm

1 stop5h 30m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 4/12

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Mon 4/20

4:15 pm-10:45 pm

1 stop5h 30m

$210

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/27

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 2/23

11:00 am-6:45 pm

1 stop6h 45m

$211

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 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

Fastest flight time

4h 20m

Direct flights

None
The fastest flight from Montreal to Chicago Midway Airport takes 4h 20m
There are no direct flights from Montreal to Chicago Midway Airport. There are no popular flight routes from Montreal to Chicago Midway Airport.
Search flight deals

  • How far is Montreal to Chicago Midway by plane?

    There are 752.3 mi between Montreal and Chicago Midway. 4h 20m 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
394 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
Portage
Lansing
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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