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$162+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
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 June, booked 77 days in advance, depart on a Friday or Thursday and return on a Thursday

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 octubre 28, 2025.

This Trip.com deal was found by Cheapflights users on 10/27. 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. 12/1111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
lun. 12/1511:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/27$263
This Ticket deal was found by Cheapflights users on 10/28. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/206:15 pmYUL - ORD
Nonstop2h 45mAir Canada
lun. 11/247:05 amORD - YUL
Nonstop2h 05mAir Canada
Deal found 10/28$264
This Trip.com deal was found by Cheapflights users on 10/28. 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.
vie. 12/126:45 amYUL - MDW
1 stop4h 20mPorter Airlines
dom. 12/1411:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/28$264
This Trip.com deal was found by Cheapflights users on 10/26. 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. 12/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
vie. 12/1211:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/26$265
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/68:55 amYUL - MDW
1 stop3h 55mPorter Airlines
jue. 12/1111:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/28$267
This SmartFares deal was found by Cheapflights users on 10/27. 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.
lun. 11/172:00 pmYUL - ORD
1 stop6h 30mAir Canada
dom. 11/238:00 amORD - YUL
1 stop4h 22mAir Canada
Deal found 10/27$268
This SmartFares deal was found by Cheapflights users on 10/28. 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.
jue. 12/1810:15 amYUL - MDW
1 stop6h 05mPorter Airlines
lun. 1/1211:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/28$268
This Trip.com deal was found by Cheapflights users on 10/28. 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.
sáb. 11/228:55 amYUL - MDW
1 stop3h 55mPorter Airlines
sáb. 11/2912:45 pmMDW - YUL
1 stop5h 05mPorter Airlines
Deal found 10/28$270
This Trip.com deal was found by Cheapflights users on 10/27. 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. 12/116:45 amYUL - MDW
1 stop4h 20mPorter Airlines
jue. 12/1811:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Deal found 10/27$272
This Air Canada deal was found by Cheapflights users on 10/27. 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.
sáb. 11/226:15 pmYUL - ORD
Nonstop2h 45mAir Canada
lun. 11/247:05 amORD - YUL
Nonstop2h 05mAir Canada
Deal found 10/27$273
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/256:00 amYUL - ORD
Nonstop3h 00mUnited Airlines
mar. 12/210:38 amORD - YUL
Nonstop2h 22mUnited Airlines
Deal found 10/27$274
This Trip.com deal was found by Cheapflights users on 10/26. 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. 12/410:15 amYUL - MDW
1 stop6h 05mPorter Airlines
dom. 12/711:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/26$275

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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$225
(United Airlines)

One-way from

$162
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$396

Good round-trip deal

$352 or less

Good one-way deal

$260 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 ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 28, 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 - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb. 4/4

9:25 am-10:57 am

Nonstop2h 32m

Chicago O'Hare Intl

mié. 4/8

9:00 am-4:21 pm

1 stop6h 21m

$225

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

lun. 3/2

3:11 pm-7:48 pm

1 stop5h 37m

Chicago O'Hare Intl

lun. 3/9

7:00 am-5:55 pm

1 stop9h 55m

$230

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

vie. 3/20

9:25 am-11:18 am

Nonstop2h 53m

Chicago O'Hare Intl

dom. 3/29

7:55 am-1:21 pm

1 stop4h 26m

$249

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb. 4/4

6:00 am-9:35 am

1 stop4h 35m

Chicago O'Hare Intl

mié. 4/8

7:10 am-5:04 pm

1 stop8h 54m

$256

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

vie. 3/20

7:00 am-2:33 pm

1 stop8h 33m

Chicago O'Hare Intl

lun. 3/23

8:15 pm-1:53 am

1 stop4h 38m

$264

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 1/8

4:00 pm-12:01 am

2 stops9h 01m

Chicago Midway

vie. 1/16

11:00 am-4:30 pm

1 stop4h 30m

$265

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mar. 12/30

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

sáb. 1/3

4:15 pm-10:45 pm

1 stop5h 30m

$268

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

sáb. 11/22

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

sáb. 11/29

12:45 pm-6:50 pm

1 stop5h 05m

$270

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mar. 11/25

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

mar. 12/2

10:38 am-2:00 pm

Nonstop2h 22m

$274

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

lun. 3/2

12:45 pm-9:46 pm

1 stop10h 01m

Chicago Midway

lun. 3/9

2:00 pm-11:39 pm

1 stop8h 39m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 39 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 October.
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 October 24, 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, 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 March is currently the most expensive (average of $256). 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 octubre 28, 2025.

It’s optimal to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in the evening. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight at noon.

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. 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 octubre 28, 2025.

The most flights from YUL to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (17 on average).

How much does it cost to fly round-trip from Montreal Pierre Elliott Trudeau Intl Airport to Chicago?

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

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 octubre 28, 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
384 reviews

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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
10,371 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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 32m. Fly via United Airlines, Air Canada, or Porter 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 65% 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 United Airlines. According to our data, you can fly for as low as $163. Users have also found prices from $163 and $167 on Air Canada and Porter 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 (97%), Qantas Airways (95%), Emirates( 93%).

  • 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 $137. On average you can expect to pay $437. 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 March is currently the most expensive (average of $256). 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
Merrillville
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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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$402FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$177Average$401FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$226Average$309FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$251Average$414FlexibilityNo cancel feeOn-time71%

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