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$138+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 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 July 29, 2025.

Round-trip from

$167
(Kiwi.com)

One-way from

$138
(Delta)

Popular in

July

Cheapest in

September

Average price

$382

Good round-trip deal

$388 or less

Good one-way deal

$229 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. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Mon 9/229:35 amMDW - YUL
1 stop8h 10mPorter Airlines
Deal found 7/28$167
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/118:20 amYUL - ORD
Nonstop2h 31mAir Canada
Thu 9/188:25 pmORD - YUL
1 stop4h 25mAir Canada
Deal found 7/28$173
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:29 pmYUL - ORD
Nonstop2h 36mAmerican Airlines
Mon 9/15:20 amORD - YUL
1 stop7h 19mAmerican Airlines
Deal found 7/27$174
This flygcity.se deal was found by Cheapflights users on 7/27. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:15 amYUL - ORD
2 stops10h 27mMultiple Airlines
Sun 8/318:10 amORD - YUL
Nonstop2h 26mMultiple Airlines
Deal found 7/27$190
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/59:28 amYUL - ORD
1 stop7h 43mDelta
Wed 11/1210:35 amORD - YUL
1 stop4h 25mDelta
Deal found 7/27$216
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:00 amYUL - MDW
1 stop7h 28mDelta
Wed 9/34:25 pmMDW - YUL
1 stop6h 28mDelta
Deal found 7/27$216
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 8/234:55 pmYUL - ORD
Nonstop2h 46mUnited Airlines
Sat 8/306:00 pmORD - YUL
Nonstop2h 29mUnited Airlines
Deal found 7/27$264
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:36 pmYUL - MDW
1 stop10h 38mMultiple Airlines
Sun 10/125:20 pmMDW - YUL
1 stop3h 55mMultiple Airlines
Deal found 7/27$264
This Kissandfly.com deal was found by Cheapflights users on 7/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:15 amYUL - ORD
Nonstop2h 46mLufthansa
Sun 8/247:11 amORD - YUL
Nonstop2h 29mLufthansa
Deal found 7/28$279

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 July 29, 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

Fri 9/19

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 9/22

9:35 am-6:45 pm

1 stop8h 10m

$167

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/11

8:20 am-9:51 am

Nonstop2h 31m

Chicago O'Hare Intl

Thu 9/18

8:25 pm-1:50 am

1 stop4h 25m

$173

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 8/26

5:29 pm-7:05 pm

Nonstop2h 36m

Chicago O'Hare Intl

Mon 9/1

5:20 am-1:39 pm

1 stop7h 19m

$174

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 8/30

8:15 am-5:42 pm

2 stops10h 27m

Chicago O'Hare Intl

Sun 8/31

8:10 am-11:36 am

Nonstop2h 26m

$190

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 8/30

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Wed 9/3

4:25 pm-11:53 pm

1 stop6h 28m

$216

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 8/23

4:55 pm-6:41 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sat 8/30

6:00 pm-9:29 pm

Nonstop2h 29m

$264

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/10

12:36 pm-10:14 pm

1 stop10h 38m

Chicago Midway

Sun 10/12

5:20 pm-10:15 pm

1 stop3h 55m

$264

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 8/21

6:15 am-8:01 am

Nonstop2h 46m

Chicago O'Hare Intl

Sun 8/24

7:11 am-10:40 am

Nonstop2h 29m

$279

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 9/30

5:00 pm-10:23 pm

1 stop6h 23m

$138

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/28

7:00 am-1:08 pm

1 stop7h 08m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 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 July 25, 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 July 29, 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 4% on the cost of your flight, compared to a flight in the morning.

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 July 29, 2025.

The most flights from YUL to CHI are scheduled on a Tuesday (31 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (29 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 July 29, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta, and United 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
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,977 reviews
Porter Airlines
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,899 reviews
Porter Airlines
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,973 reviews
Porter Airlines
8.0
Very good
317 reviews

Food

7.6

Crew

8.7

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

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

    Porter Airlines, at $167, 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 American Airlines. Porter Airlines is 48% 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 Delta. According to our data, you can fly for as low as $138. Users have also found prices from $145 and $145 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: Qantas Airways (95%), Qatar Airways (93%), Emirates( 91%).

  • 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 $1,347. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for $192.

  • 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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 5 airlines flying from Pierre Elliott Trudeau Intl to Chicago

Discover the top 5 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$487FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$217Average$441FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$217Average$325FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$275Average$407FlexibilityNo cancel feeOn-time71%
WestJetCheapest$334Average$340FlexibilityNo cancel feeOn-time60%

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