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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from $164

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 Pierre Elliott Trudeau Intl Airport to Chicago departing on 9/23. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Montreal Pierre Elliott Trudeau Intl Airport 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
3:20 pm - 9:10 pm
MDW
-
YUL
4h 50m
1 stop
$272Porter Airlines
Mon, Sep 7 - Fri, Sep 11
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:25 am - 6:10 pm
MDW
-
YUL
6h 45m
1 stop
$275Porter Airlines
Mon, Aug 10 - Thu, Aug 20
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$276Porter Airlines
Wed, Aug 5 - Sun, Aug 9
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
3:15 pm - 10:10 pm
MDW
-
YUL
5h 55m
1 stop
$277Porter Airlines
Thu, Aug 6 - Thu, Aug 27
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$278Porter Airlines
Thu, Aug 6 - Sun, Aug 9
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:15 pm - 8:10 pm
MDW
-
YUL
3h 55m
1 stop
$279Porter Airlines
Wed, Aug 5 - Mon, Aug 10
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$281Porter Airlines
Thu, Aug 6 - Sun, Aug 9
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$282Porter Airlines
Fri, Aug 21 - Sun, Aug 23
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$283Porter Airlines
Thu, Aug 6 - Sun, Aug 9
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:20 am - 6:10 pm
MDW
-
YUL
6h 50m
1 stop
$284Porter Airlines
Fri, Aug 7 - Sun, Aug 9

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Delta flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Our best Delta deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight tickets
Delta
Aug 23
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 26
MDW1:25 pmChicago Midway
9h 05m
1 stop
YUL11:30 pmMontreal Pierre Elliott Trudeau Intl
$286
Delta
Aug 13
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 39m
1 stop
MDW12:39 pmChicago Midway
Aug 15
MDW1:25 pmChicago Midway
9h 05m
1 stop
YUL11:30 pmMontreal Pierre Elliott Trudeau Intl
$293
Delta
Dec 9
YUL12:45 pmMontreal Pierre Elliott Trudeau Intl
6h 52m
1 stop
MDW6:37 pmChicago Midway
Dec 12
MDW6:30 pmChicago Midway
3h 40m
1 stop
YUL11:10 pmMontreal Pierre Elliott Trudeau Intl
$313

Porter Airlines flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

Our best Porter Airlines deals on Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport flight tickets
Porter Airlines
Aug 25
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 amChicago Midway
Aug 30
MDW3:15 pmChicago Midway
3h 55m
1 stop
YUL8:10 pmMontreal Pierre Elliott Trudeau Intl
$271
Porter Airlines
Sep 7
YUL10:35 amMontreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 pmChicago Midway
Sep 11
MDW3:20 pmChicago Midway
4h 50m
1 stop
YUL9:10 pmMontreal Pierre Elliott Trudeau Intl
$272
Porter Airlines
Aug 10
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
4h 15m
1 stop
MDW9:45 amChicago Midway
Aug 20
MDW10:25 amChicago Midway
6h 45m
1 stop
YUL6:10 pmMontreal Pierre Elliott Trudeau Intl
$275

momondo Fare Finder

 
Customize your flight search to find flights from Montreal Pierre Elliott Trudeau Intl Airport 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 July 14, 2026.
Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport 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

Mon 9/7

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Fri 9/11

3:20 pm-9:10 pm

1 stop4h 50m

$272

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 8/10

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Thu 8/20

10:25 am-6:10 pm

1 stop6h 45m

$275

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 8/5

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$276

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Thu 8/27

3:15 pm-10:10 pm

1 stop5h 55m

$277

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$278
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 8/5

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Mon 8/10

3:15 pm-8:10 pm

1 stop3h 55m

$279

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 8/21

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Sun 8/23

10:20 am-6:10 pm

1 stop6h 50m

$282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/6

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$283

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 8/7

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Sun 8/9

10:20 am-6:10 pm

1 stop6h 50m

$284

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 Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport 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 Pierre Elliott Trudeau Intl Airport, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Montreal Pierre Elliott Trudeau Intl Airport during the month May is also very affordable. Most momondo users find prices during this month for around $175.

When to book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

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

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

Fastest flight time

4h 10m

Direct flights

None
The fastest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport takes 4h 10m
There are no direct flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport. There are no popular flight routes from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

  • How far is Montreal Pierre Elliott Trudeau Intl to Chicago Midway by plane?

    The distance between Montreal Pierre Elliott Trudeau Intl and Chicago Midway is about 742.9 mi. By plane, this route typically takes 4h 10m.

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

    Prices for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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
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Why use momondo?

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

Finding the right flight to Chicago from Montreal is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Montreal to Chicago flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Montreal. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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