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Cheap flights from Montreal to Chicago from $105

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 4/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
3:20 pm - 10:10 pm
MDW
-
YUL
5h 50m
1 stop
$156Porter Airlines
Thu, Apr 30 - Mon, May 11
Porter Airlines Logo
9:50 am - 3:20 pm
YUL
-
MDW
6h 30m
1 stop
Porter Airlines Logo
4:05 pm - 10:45 pm
MDW
-
YUL
5h 40m
1 stop
$157Porter Airlines
Sun, Apr 19 - Fri, Apr 24
Porter Airlines Logo
6:30 am - 9:40 am
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 am - 5:15 pm
MDW
-
YUL
5h 50m
1 stop
$158Porter Airlines
Fri, May 8 - Mon, May 11
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
4:05 pm - 10:45 pm
MDW
-
YUL
5h 40m
1 stop
$159Porter Airlines
Wed, Apr 15 - Fri, Apr 24
Porter Airlines Logo
6:30 am - 9:40 am
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
3:20 pm - 8:10 pm
MDW
-
YUL
3h 50m
1 stop
$163Porter Airlines
Fri, May 8 - Sun, May 10
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 am - 5:15 pm
MDW
-
YUL
5h 50m
1 stop
$165Porter Airlines
Thu, Jun 4 - Mon, Jun 8
Porter Airlines Logo
6:50 am - 10:05 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
$167Porter Airlines
Thu, Mar 26 - Mon, Mar 30
Porter Airlines Logo
6:50 am - 10:05 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
11:00 am - 4:30 pm
MDW
-
YUL
4h 30m
1 stop
$169Porter Airlines
Thu, Mar 26 - Mon, Mar 30
Porter Airlines Logo
6:50 am - 10:05 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
$170Porter Airlines
Thu, Mar 26 - Mon, Mar 30
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 am - 4:30 pm
MDW
-
YUL
4h 30m
1 stop
$171Porter Airlines
Thu, Apr 16 - Thu, Apr 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 30
YUL6:50 amMontreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:15 amChicago Midway
May 11
MDW10:25 amChicago Midway
5h 50m
1 stop
YUL5:15 pmMontreal Pierre Elliott Trudeau Intl
$156
Porter Airlines
Apr 19
YUL9:50 amMontreal Pierre Elliott Trudeau Intl
6h 30m
1 stop
MDW3:20 pmChicago Midway
Apr 24
MDW4:05 pmChicago Midway
5h 40m
1 stop
YUL10:45 pmMontreal Pierre Elliott Trudeau Intl
$157
Porter Airlines
Apr 30
YUL6:50 amMontreal Pierre Elliott Trudeau Intl
4h 25m
1 stop
MDW10:15 amChicago Midway
May 12
MDW3:20 pmChicago Midway
5h 50m
1 stop
YUL10:10 pmMontreal Pierre Elliott Trudeau Intl
$158

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Apr 23
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 43m
1 stop
MDW12:43 pmChicago Midway
May 2
MDW5:21 pmChicago Midway
5h 30m
1 stop
YUL11:51 pmMontreal Pierre Elliott Trudeau Intl
$207
Delta
Mar 16
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 29m
1 stop
MDW12:29 pmChicago Midway
Mar 17
MDW12:47 pmChicago Midway
9h 58m
1 stop
YUL11:45 pmMontreal Pierre Elliott Trudeau Intl
$218
Delta
Jun 6
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 42m
1 stop
MDW12:42 pmChicago Midway
Jun 12
MDW2:00 pmChicago Midway
8h 34m
1 stop
YUL11:34 pmMontreal Pierre Elliott Trudeau Intl
$219

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 March 4, 2026.
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

Thu 4/30

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Mon 5/11

3:20 pm-10:10 pm

1 stop5h 50m

$156

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 4/19

9:50 am-3:20 pm

1 stop6h 30m

Chicago Midway

Fri 4/24

4:05 pm-10:45 pm

1 stop5h 40m

$157

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/8

6:30 am-9:40 am

1 stop4h 10m

Chicago Midway

Mon 5/11

10:25 am-5:15 pm

1 stop5h 50m

$158

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 4/15

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Fri 4/24

4:05 pm-10:45 pm

1 stop5h 40m

$159

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/8

6:30 am-9:40 am

1 stop4h 10m

Chicago Midway

Sun 5/10

3:20 pm-8:10 pm

1 stop3h 50m

$163

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 6/4

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 6/8

10:25 am-5:15 pm

1 stop5h 50m

$165

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/30

11:00 am-5:45 pm

1 stop5h 45m

$167

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/30

11:00 am-4:30 pm

1 stop4h 30m

$169

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/30

11:00 am-5:45 pm

1 stop5h 45m

$170

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/16

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Thu 4/23

11:00 am-4:30 pm

1 stop4h 30m

$171

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 typical price of a round-trip flight between Montreal and Chicago Midway Airport?

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 10m

Direct flights

None
The fastest flight from Montreal to Chicago Midway Airport takes 4h 10m
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 10m 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 $158Free CancellationRating
8.0
421 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
Valparaiso
Schererville
Munster
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

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