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Cheap flights from Montreal to Chicago from $137

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 9/30. 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

Delta Logo
7:00 am - 4:09 pmYUL-MDW
10h 09m1 stop
Delta Logo
5:04 pm - 11:48 pmMDW-YUL
5h 44m1 stop
$215Delta
Find Deal
Wed, Oct 22 - Tue, Oct 28
Delta Logo
10:57 am - 5:35 pmYUL-MDW
7h 38m1 stop
Delta Logo
6:15 pm - 11:29 pmMDW-YUL
4h 14m1 stop
$235Delta
Find Deal
Sat, Sep 27 - Mon, Sep 29
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 am - 4:00 pmMDW-YUL
5h 25m1 stop
$236Porter Airlines
Find Deal
Thu, Sep 11 - Sun, Sep 14
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$237Porter Airlines
Find Deal
Thu, Sep 11 - Sun, Sep 14
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
9:35 am - 4:00 pmMDW-YUL
5h 25m1 stop
$238Porter Airlines
Find Deal
Fri, Sep 12 - Sun, Sep 14
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$239Porter Airlines
Find Deal
Tue, Sep 16 - Sun, Sep 21
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$240Porter Airlines
Find Deal
Thu, Sep 18 - Mon, Sep 22
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$241Porter Airlines
Find Deal
Thu, Sep 4 - Tue, Sep 9
Delta Logo
7:00 am - 11:48 amYUL-MDW
5h 48m1 stop
Delta Logo
12:43 pm - 11:56 pmMDW-YUL
10h 13m1 stop
$252Delta
Find Deal
Tue, Sep 16 - Tue, Sep 23
Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Logo
9:32 am - 10:10 pmMDW-YUL
11h 38m2 stops
$294
Find Deal
Tue, Oct 7 - Fri, Oct 31

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Oct 22
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
10h 09m
1 stop
MDW4:09 pmChicago Midway
Oct 28
MDW5:04 pmChicago Midway
5h 44m
1 stop
YUL11:48 pmMontreal Pierre Elliott Trudeau Intl
$215
Find similar
Delta
Sep 27
YUL10:57 amMontreal Pierre Elliott Trudeau Intl
7h 38m
1 stop
MDW5:35 pmChicago Midway
Sep 29
MDW6:15 pmChicago Midway
4h 14m
1 stop
YUL11:29 pmMontreal Pierre Elliott Trudeau Intl
$235
Find similar
Delta
Sep 16
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
5h 48m
1 stop
MDW11:48 amChicago Midway
Sep 23
MDW12:43 pmChicago Midway
10h 13m
1 stop
YUL11:56 pmMontreal Pierre Elliott Trudeau Intl
$252
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
Sep 11
YUL1:10 pmMontreal Pierre Elliott Trudeau Intl
4h 14m
1 stop
MDW4:24 pmChicago Midway
Sep 14
MDW9:35 amChicago Midway
5h 25m
1 stop
YUL4:00 pmMontreal Pierre Elliott Trudeau Intl
$236
Find similar
Porter Airlines
Sep 11
YUL10:45 amMontreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 pmChicago Midway
Sep 14
MDW5:20 pmChicago Midway
3h 55m
1 stop
YUL10:15 pmMontreal Pierre Elliott Trudeau Intl
$237
Find similar
Porter Airlines
Sep 12
YUL10:45 amMontreal Pierre Elliott Trudeau Intl
6h 39m
1 stop
MDW4:24 pmChicago Midway
Sep 14
MDW9:35 amChicago Midway
5h 25m
1 stop
YUL4:00 pmMontreal Pierre Elliott Trudeau Intl
$238
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 August 20, 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

Wed 10/22

7:00 am-4:09 pm

1 stop10h 09m

Chicago Midway

Tue 10/28

5:04 pm-11:48 pm

1 stop5h 44m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 9/27

10:57 am-5:35 pm

1 stop7h 38m

Chicago Midway

Mon 9/29

6:15 pm-11:29 pm

1 stop4h 14m

$235

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/11

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Sun 9/14

9:35 am-4:00 pm

1 stop5h 25m

$236

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/11

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 9/14

5:20 pm-10:15 pm

1 stop3h 55m

$237

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/12

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 9/14

9:35 am-4:00 pm

1 stop5h 25m

$238

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/16

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 9/21

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/18

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Mon 9/22

5:20 pm-10:15 pm

1 stop3h 55m

$240

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Tue 9/9

5:20 pm-10:15 pm

1 stop3h 55m

$241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/16

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 9/23

12:43 pm-11:56 pm

1 stop10h 13m

$252

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/7

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Fri 10/31

9:32 am-10:10 pm

2 stops11h 38m

$294

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

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
336 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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