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$163+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheapflights Tip: The best prices from Montreal Pierre Elliott Trudeau Intl to Chicago are usually found in September or May, booked 78 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 December 15, 2025.

This FlightHub deal was found by Cheapflights users on 12/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 2/2311:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 12/13$196
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sun 1/411:05 amMDW - YUL
1 stop5h 40mPorter Airlines
Deal found 12/14$305
This Air Canada deal was found by Cheapflights users on 12/13. 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.
Sat 12/277:00 amYUL - ORD
1 stop7h 01mAir Canada
Mon 2/236:00 pmORD - YUL
Nonstop2h 17mAir Canada
Deal found 12/13$331
This eDestinos deal was found by Cheapflights users on 12/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sun 12/284:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/14$343
This Trip.com deal was found by Cheapflights users on 12/14. 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.
Mon 12/226:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Tue 12/304:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/14$345
This Trip.com deal was found by Cheapflights users on 12/13. 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.
Thu 12/2510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Sun 12/284:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/13$353
This FlightHub deal was found by Cheapflights users on 12/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Sat 1/311:05 amMDW - YUL
1 stop4h 25mPorter Airlines
Deal found 12/13$374
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sun 12/284:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/14$377
This Air Canada deal was found by Cheapflights users on 12/15. 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.
Mon 12/221:10 pmYUL - ORD
Nonstop2h 45mAir Canada
Tue 1/68:00 amORD - YUL
1 stop4h 22mAir Canada
Deal found 12/15$388
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:10 pmYUL - ORD
Nonstop2h 45mAir Canada
Mon 1/58:45 pmORD - YUL
1 stop10h 37mAir Canada
Deal found 12/15$397
This Booking.com deal was found by Cheapflights users on 12/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:50 amYUL - ORD
2 stops7h 20mAir Canada
Tue 12/302:00 pmORD - YUL
2 stops5h 50mAir Canada
Deal found 12/13$399
This Trip.com deal was found by Cheapflights users on 12/13. 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.
Sat 12/206:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 12/2911:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 12/13$399

Find 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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Air Canada)

One-way from

$163
(Air Canada)

Popular in

July

Cheapest in

September

Average price

$342

Good round-trip deal

$400 or less

Good one-way deal

$233 or less
Provider with most accurate pricing for Montreal Pierre Elliott Trudeau Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montreal Pierre Elliott Trudeau Intl-Chicago (CHI) flights.
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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. 2% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in December 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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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 December 15, 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

Thu 2/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sat 2/14

12:45 pm-6:45 pm

1 stop5h 00m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Wed 2/18

11:00 am-6:45 pm

1 stop6h 45m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Mon 2/16

4:15 pm-10:45 pm

1 stop5h 30m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Fri 2/20

11:00 am-5:45 pm

1 stop5h 45m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Tue 2/17

11:00 am-6:45 pm

1 stop6h 45m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Thu 2/19

11:00 am-5:45 pm

1 stop5h 45m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Fri 2/20

11:00 am-5:45 pm

1 stop5h 45m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 2/14

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Tue 2/17

11:00 am-4:30 pm

1 stop4h 30m

$189

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Thu 2/19

11:00 am-5:45 pm

1 stop5h 45m

$189

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 2/12

6:00 am-9:41 am

1 stop4h 41m

Chicago O'Hare Intl

Sat 2/14

2:03 pm-11:10 pm

1 stop8h 07m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 47 results
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Compare providers for flights from Pierre Elliott Trudeau Intl to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pierre Elliott Trudeau Intl to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Montreal Pierre Elliott Trudeau Intl Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Montreal Pierre Elliott Trudeau Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montreal Pierre Elliott Trudeau Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 12, 2025.

The best time to book flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is 78 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, September is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of $131). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in December is currently the most expensive (average of $271). 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 December 15, 2025.

It’s optimal to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in the afternoon. By choosing this option you can save up to 60% on the cost of your flight, compared to a flight in the evening.

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 Thursday evenings when fares are most often at their lowest. Sunday 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 December 15, 2025.

The most flights from YUL to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

The best insider tips for Montreal Pierre Elliott Trudeau Intl Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 15, 2025.
Get a feel of what it's like to fly with Porter Airlines and Air Canada 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
8.0
Very good
399 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,525 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 4h 20m. Fly via Porter Airlines or Delta to get the fastest option. The distance from Montreal Pierre Elliott Trudeau Intl Airport to Chicago is about 743 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?

    Air Canada, at $156, was found to be the cheapest airline from Montreal Pierre Elliott Trudeau Intl Airport to Chicago.Alternate airlines to your destination round-trip include Porter Airlines and American Airlines. Air Canada is 50% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $104. Users have also found prices from $136 and $148 on American Airlines and United Airlines, respectively.

  • 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: Qatar Airways (94%), ANA (90%), Emirates( 89%).

  • 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 $155. On average you can expect to pay $1,163. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for $187.

  • 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, September is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of $131). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in December is currently the most expensive (average of $271). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$156Average$337FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$217Average$300FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$251Average$414FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$267Average$402FlexibilityNo cancel feeOn-time69%

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