Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from $163

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 9/4. 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
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$273Porter Airlines
Wed, Sep 16 - Wed, Sep 16
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$274Porter Airlines
Fri, Sep 18 - Mon, Sep 21
Porter Airlines Logo
10:35 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 00m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$275Porter Airlines
Wed, Sep 2 - Wed, Sep 30
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$277Porter Airlines
Thu, Oct 15 - Thu, Oct 22
Delta Logo
12:47 pm - 4:59 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:45 pm - 11:59 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
10h 14m1 stop Atlanta Hartsfield-Jackson
$278Delta
Wed, Sep 2 - Tue, Oct 20
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$279Porter Airlines
Thu, Sep 24 - Sun, Sep 27
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$280Porter Airlines
Tue, Sep 15 - Thu, Sep 17
Porter Airlines Logo
10:35 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 00m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$281Porter Airlines
Wed, Sep 2 - Tue, Sep 8
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$282Porter Airlines
Thu, Sep 10 - Sun, Sep 13
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$283Porter Airlines
Fri, Sep 11 - Sun, Sep 13

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
Sep 2
YUL12:47 pmMontreal Pierre Elliott Trudeau Intl
5h 12m
1 stop
MDW4:59 pmChicago Midway
Oct 20
MDW12:45 pmChicago Midway
10h 14m
1 stop
YUL11:59 pmMontreal Pierre Elliott Trudeau Intl
$278
Delta
Sep 5
YUL2:46 pmMontreal Pierre Elliott Trudeau Intl
8h 50m
1 stop
MDW10:36 pmChicago Midway
Sep 19
MDW6:40 pmChicago Midway
3h 47m
1 stop
YUL11:27 pmMontreal Pierre Elliott Trudeau Intl
$284
Delta
Feb 3
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 33m
1 stop
MDW12:33 pmChicago Midway
Feb 9
MDW10:35 amChicago Midway
5h 28m
1 stop
YUL5:03 pmMontreal Pierre Elliott Trudeau Intl
$292

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
Sep 16
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 amChicago Midway
Sep 16
MDW3:20 pmChicago Midway
4h 52m
1 stop
YUL9:12 pmMontreal Pierre Elliott Trudeau Intl
$273
Porter Airlines
Sep 18
YUL9:00 amMontreal Pierre Elliott Trudeau Intl
6h 35m
1 stop
MDW2:35 pmChicago Midway
Sep 21
MDW3:20 pmChicago Midway
4h 52m
1 stop
YUL9:12 pmMontreal Pierre Elliott Trudeau Intl
$274
Porter Airlines
Sep 2
YUL10:35 amMontreal Pierre Elliott Trudeau Intl
5h 00m
1 stop
MDW2:35 pmChicago Midway
Sep 30
MDW3:20 pmChicago Midway
4h 52m
1 stop
YUL9:12 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 August 13, 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 Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/16

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Wed 9/16

3:20 pm-9:12 pm

1 stop4h 52m

$273

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/18

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Mon 9/21

3:20 pm-9:12 pm

1 stop4h 52m

$274
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/2

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Wed 9/30

3:20 pm-9:12 pm

1 stop4h 52m

$275

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/15

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Thu 10/22

3:20 pm-9:12 pm

1 stop4h 52m

$277

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/2

12:47 pm-4:59 pm

1 stop5h 12m

Chicago Midway

Tue 10/20

12:45 pm-11:59 pm

1 stop10h 14m

$278

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/24

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sun 9/27

11:45 am-6:12 pm

1 stop5h 27m

$279

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/15

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Thu 9/17

3:20 pm-9:12 pm

1 stop4h 52m

$280

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/2

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Tue 9/8

11:45 am-6:12 pm

1 stop5h 27m

$281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/10

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sun 9/13

11:45 am-6:12 pm

1 stop5h 27m

$282

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/11

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Sun 9/13

11:45 am-6:12 pm

1 stop5h 27m

$283

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 cheapest month to fly to Chicago Midway Airport?

The month of March 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 March, then departing from Montreal Pierre Elliott Trudeau Intl Airport during the month January is also very affordable. Most momondo users find prices during this month for around $0.

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 15m

Direct flights

None
The fastest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport takes 4h 15m
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 15m.

  • 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
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 9/12
Sat 9/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago