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$127+ Cheap flights from Pierre Elliott Trudeau Intl (YUL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Montreal Pierre Elliott Trudeau Intl to Chicago are usually found in June or September, booked 77 days in advance, depart on a Saturday or Thursday and return on a Thursday

Cheap flight deals from Pierre Elliott Trudeau Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pierre Elliott Trudeau Intl (YUL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 11, 2025.

Round-trip from

$209
(Kiwi.com)

One-way from

$127
(SmartFares)

Popular in

December

Cheapest in

June

Average price

$306

Good round-trip deal

$394 or less

Good one-way deal

$261 or less
From Montreal Pierre Elliott Trudeau Intl to Chicago (CHI)
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One-way flight from Montreal Pierre Elliott Trudeau Intl to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Montreal Pierre Elliott Trudeau Intl to Chicago (CHI).
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Price to beat on a one-way flight from Montreal Pierre Elliott Trudeau Intl to Chicago (CHI).
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Find flight deals from Pierre Elliott Trudeau Intl to Chicago

Cheapest flights from Pierre Elliott Trudeau Intl to Chicago
Explore the most affordable flight options available from Pierre Elliott Trudeau Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
mar. 11/1111:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/8$209
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/171:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
lun. 10/205:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9$210
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
vie. 11/2811:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 9/10$211
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/71:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
mié. 10/159:35 amMDW - YUL
1 stop5h 25mPorter Airlines
Deal found 9/9$214
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/710:45 amYUL - MDW
1 stop6h 39mPorter Airlines
vie. 10/245:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9$215
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2011:25 amYUL - MDW
1 stop4h 55mPorter Airlines
jue. 11/274:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 9/10$216
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/810:45 amYUL - MDW
1 stop6h 39mPorter Airlines
dom. 10/125:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/10$218
This SmartFares deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/1611:25 amYUL - MDW
1 stop4h 55mPorter Airlines
mar. 11/1811:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/8$221
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/196:45 amYUL - MDW
1 stop4h 20mPorter Airlines
mar. 12/911:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/9$223
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/99:25 amYUL - ORD
Nonstop2h 53mAir Canada
mar. 11/1112:50 pmORD - YUL
Nonstop2h 07mAir Canada
Deal found 9/8$229
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/168:20 amYUL - ORD
Nonstop2h 31mAir Canada
dom. 10/198:40 amORD - YUL
Nonstop2h 14mAir Canada
Deal found 9/9$231
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/78:20 amYUL - ORD
Nonstop2h 31mAir Canada
dom. 10/128:40 amORD - YUL
Nonstop2h 14mAir Canada
Deal found 9/9$234

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pierre Elliott Trudeau Intl to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 11, 2025.
Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago that are best for you.

Fly from

Pierre Elliott Trudeau Intl

Fly to

Chicago

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 11/20

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

dom. 11/23

11:00 am-4:30 pm

1 stop4h 30m

$209

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 10/2

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

lun. 10/6

5:20 pm-10:15 pm

1 stop3h 55m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 11/21

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

lun. 11/24

11:00 am-4:30 pm

1 stop4h 30m

$227

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 10/17

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

lun. 10/20

5:20 pm-10:15 pm

1 stop3h 55m

$237

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 10/8

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

jue. 10/9

9:35 am-4:00 pm

1 stop5h 25m

$238

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 10/17

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

mar. 10/21

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

mié. 10/22

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 10/15

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

dom. 10/19

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 10/31

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

dom. 11/2

11:00 am-6:45 pm

1 stop6h 45m

$240

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 11/20

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

jue. 11/27

11:00 am-4:30 pm

1 stop4h 30m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 46 results
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The best insider tips for Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Montreal Pierre Elliott Trudeau Intl Airport to Chicago trip
Airports
YUL

Use YULExpress to pre-book security fast track up to 72 hours before departure for a smoother experience.

Read more about YULby John Walton
ORD

Take the 'L' train from ORD to downtown Chicago for a reliable and cost-effective transit option.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on YUL

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

Best time to book a flight from Pierre Elliott Trudeau Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pierre Elliott Trudeau Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

How far ahead should I book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Pierre Elliott Trudeau Intl to Chicago. Price data was last updated on August 29, 2025.

The best time to book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of $245). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YUL to CHI?

Find hourly flight availability from Pierre Elliott Trudeau Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 11, 2025.

It’s optimal to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago at noon. By choosing this option you can save up to 9% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Pierre Elliott Trudeau Intl to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Montreal Pierre Elliott Trudeau Intl Airport to Chicago

Explore weekly flight availability from Pierre Elliott Trudeau Intl to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 11, 2025.

The most flights from YUL to CHI are scheduled on a Wednesday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated septiembre 11, 2025.
Get a feel of what it's like to fly with Porter Airlines, United Airlines, and American Airlines from Montreal Pierre Elliott Trudeau Intl Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.0

Overall

7.9

Comfort

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.0

Overall

7.9

Comfort

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,937 reviews
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.0

Overall

7.9

Comfort

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.0

Overall

7.9

Comfort

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.0

Overall

7.9

Comfort

7.9

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Pierre Elliott Trudeau Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

    There are many flights that can get you from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in 2h 46m. Fly via Porter Airlines, Delta, or United Airlines to get the fastest option. The distance from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is about 745 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago round-trip?

    United Airlines, at $112, was found to be the cheapest airline from Montreal Pierre Elliott Trudeau Intl Airport to Chicago.Alternate airlines to your destination round-trip include Air Canada and Porter Airlines. United Airlines is 66% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

    Before booking your flight to Chicago from Montreal Pierre Elliott Trudeau Intl Airport, check out the most reliable airlines to get you to your destination on time: Qantas Airways (90%), Qatar Airways (90%), Emirates( 90%).

  • What are the cheapest flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

    The cheapest flight price from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is $136. On average you can expect to pay $1,247. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for $250.

  • Can I find deals for flights from Pierre Elliott Trudeau Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on Pierre Elliott Trudeau Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pierre Elliott Trudeau Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pierre Elliott Trudeau Intl to Chicago.

  • Can I find deals for business class flights from Pierre Elliott Trudeau Intl to Chicago?

    Yes. Cheapflights offers flight deals from Pierre Elliott Trudeau Intl to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of $245). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Alternative routes for Pierre Elliott Trudeau Intl to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights

Top 4 airlines flying from Pierre Elliott Trudeau Intl to Chicago

Discover the top 4 airlines that operate flights from Pierre Elliott Trudeau Intl to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$487FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$174Average$442FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$226Average$325FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$262Average$407FlexibilityNo cancel feeOn-time71%

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