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Cheap flights from Montreal to Chicago from $172

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 6/22. 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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0 bags

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Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 am - 6:10 pm
MDW
-
YUL
6h 45m
1 stop
$312Porter Airlines
Thu, Jul 23 - Tue, Jul 28
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 pm - 8:10 pm
MDW
-
YUL
3h 50m
1 stop
$315Porter Airlines
Wed, Jul 1 - Mon, Jul 6
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:15 pm - 8:10 pm
MDW
-
YUL
3h 55m
1 stop
$318Porter Airlines
Thu, Aug 13 - Mon, Aug 17
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:15 pm - 8:10 pm
MDW
-
YUL
3h 55m
1 stop
$319Porter Airlines
Thu, Aug 13 - Mon, Aug 17
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 am - 6:10 pm
MDW
-
YUL
6h 45m
1 stop
$320Porter Airlines
Wed, Jul 8 - Mon, Jul 13
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 am - 6:10 pm
MDW
-
YUL
6h 45m
1 stop
$322Porter Airlines
Thu, Jul 23 - Sun, Jul 26
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 pm - 8:10 pm
MDW
-
YUL
3h 50m
1 stop
$324Porter Airlines
Thu, Jul 23 - Tue, Jul 28
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 pm - 10:10 pm
MDW
-
YUL
5h 50m
1 stop
$325Porter Airlines
Thu, Jul 23 - Tue, Jul 28
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 am - 6:10 pm
MDW
-
YUL
6h 45m
1 stop
$326Porter Airlines
Thu, Jul 9 - Mon, Jul 13
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:20 pm - 8:10 pm
MDW
-
YUL
3h 50m
1 stop
$327Porter Airlines
Mon, Jul 13 - Tue, Jul 21

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
Jul 23
YUL10:35 amMontreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 pmChicago Midway
Jul 28
MDW10:25 amChicago Midway
6h 45m
1 stop
YUL6:10 pmMontreal Pierre Elliott Trudeau Intl
$312
Porter Airlines
Jul 1
YUL10:35 amMontreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 pmChicago Midway
Jul 6
MDW3:20 pmChicago Midway
3h 50m
1 stop
YUL8:10 pmMontreal Pierre Elliott Trudeau Intl
$315
Porter Airlines
Aug 13
YUL10:35 amMontreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 pmChicago Midway
Aug 17
MDW3:15 pmChicago Midway
3h 55m
1 stop
YUL8:10 pmMontreal Pierre Elliott Trudeau Intl
$318

Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Jun 16
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 46m
1 stop
MDW12:46 pmChicago Midway
Jun 20
MDW6:35 pmChicago Midway
3h 53m
1 stop
YUL11:28 pmMontreal Pierre Elliott Trudeau Intl
$312
Delta
Aug 15
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 17
MDW6:42 pmChicago Midway
3h 48m
1 stop
YUL11:30 pmMontreal Pierre Elliott Trudeau Intl
$339
Delta
Jul 7
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 38m
1 stop
MDW12:38 pmChicago Midway
Jul 13
MDW1:18 pmChicago Midway
9h 07m
1 stop
YUL11:25 pmMontreal Pierre Elliott Trudeau Intl
$340

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 June 3, 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

Cheapest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/23

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Tue 7/28

10:25 am-6:10 pm

1 stop6h 45m

$312
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/1

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 7/6

3:20 pm-8:10 pm

1 stop3h 50m

$315

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/13

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 8/17

3:15 pm-8:10 pm

1 stop3h 55m

$318

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/13

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 8/17

3:15 pm-8:10 pm

1 stop3h 55m

$319

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/8

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 7/13

10:25 am-6:10 pm

1 stop6h 45m

$320

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/23

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 7/26

10:25 am-6:10 pm

1 stop6h 45m

$322

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/23

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Tue 7/28

3:20 pm-8:10 pm

1 stop3h 50m

$324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/23

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Tue 7/28

3:20 pm-10:10 pm

1 stop5h 50m

$325

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 7/9

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Mon 7/13

10:25 am-6:10 pm

1 stop6h 45m

$326

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 7/13

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Tue 7/21

3:20 pm-8:10 pm

1 stop3h 50m

$327

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

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Montreal, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Montreal during the month September is also very affordable. Most momondo users find prices during this month for around $130.

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 17m

Direct flights

None
The fastest flight from Montreal to Chicago Midway Airport takes 4h 17m
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

Frequently asked questions about flying from Montreal to Chicago Midway Airport

  • How far is Montreal to Chicago Midway by plane?

    There are 752.3 mi between Montreal and Chicago Midway. 4h 17m 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 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.

Traveling to a place near Chicago?

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