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$102+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Montreal Pierre Elliott Trudeau Intl to Chicago are usually found in May or September, 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 January 29, 2026.

This Air Canada deal was found by Cheapflights users on 1/27. 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.
Thu 3/269:25 am
YUL
-
ORD
Nonstop2h 53m
Air Canada
Mon 3/3012:50 pm
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 1/27$182
This oojo deal was found by Cheapflights users on 1/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 5/410:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/27$183
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:25 pm
YUL
-
ORD
Nonstop2h 45m
Air Canada
Sat 2/217:15 am
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 1/28$184
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 2/194:45 pm
YUL
-
ORD
Nonstop3h 00m
United Airlines
Sat 2/218:50 am
ORD
-
YUL
1 stop5h 26m
United Airlines
Deal found 1/27$185
This Trip.com deal was found by Cheapflights users on 1/27. 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.
Thu 6/46:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 6/710:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/27$186
This Trip.com deal was found by Cheapflights users on 1/27. 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.
Thu 6/118:15 am
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 6/148:45 am
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 1/27$190
This Trip.com deal was found by Cheapflights users on 1/28. 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.
Thu 3/126:50 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 3/1611:00 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 1/28$194
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:35 am
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Thu 5/710:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/28$195
This FlightHub deal was found by Cheapflights users on 1/27. 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 4/2410:15 am
YUL
-
MDW
1 stop6h 05m
Porter Airlines
Mon 4/2711:00 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 1/27$196
This FlightHub deal was found by Cheapflights users on 1/27. 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 4/2411:25 am
YUL
-
MDW
1 stop4h 55m
Porter Airlines
Sun 5/310:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/27$198
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:10 pm
YUL
-
ORD
Nonstop2h 45m
Air Canada
Fri 2/277:15 am
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 1/28$200
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 2/194:45 pm
YUL
-
ORD
Nonstop3h 00m
United Airlines
Mon 2/231:02 pm
ORD
-
YUL
1 stop5h 46m
United Airlines
Deal found 1/27$206

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$182
(Air Canada)

One-way from

$102
(Trip.com)

Popular in

January

Cheapest in

May

Average price

$377

Good round-trip deal

$318 or less

Good one-way deal

$222 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. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
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 January 2026
Search Deals
Price to beat on a round-trip flight from Montreal Pierre Elliott Trudeau Intl to Chicago (CHI).
Search Deals
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 January 29, 2026.
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

Thu 3/12

9:25 am-11:18 am

Nonstop2h 53m

Chicago O'Hare Intl

Mon 3/16

12:50 pm-3:57 pm

Nonstop2h 07m

$184

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/18

9:15 am-10:53 am

Nonstop2h 38m

Chicago O'Hare Intl

Mon 4/20

12:50 pm-4:05 pm

Nonstop2h 15m

$184

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 2/19

9:15 am-2:20 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 2/21

6:00 pm-9:17 pm

Nonstop2h 17m

$191

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/12

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/16

11:00 am-5:45 pm

1 stop5h 45m

$194

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 5/4

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

Thu 5/7

10:25 am-5:15 pm

1 stop5h 50m

$195

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

2:13 pm-11:43 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 2/22

10:35 am-2:00 pm

Nonstop2h 25m

$206

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

7:00 am-4:51 pm

1 stop10h 51m

Chicago O'Hare Intl

Wed 3/11

7:10 am-5:31 pm

1 stop9h 21m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/20

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Sat 2/21

1:28 pm-11:10 pm

1 stop8h 42m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/10

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 4/13

11:00 am-4:30 pm

1 stop4h 30m

$217

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 5/4

12:50 pm-9:25 pm

1 stop9h 35m

Chicago O'Hare Intl

Sat 5/9

1:15 pm-11:58 pm

1 stop9h 43m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 42 results
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  • Most accurate provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montreal Pierre Elliott Trudeau Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 23, 2026.

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 March is currently the most expensive (average of $248). 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 January 29, 2026.

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 52% 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 January 24, 2026.

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 January 29, 2026.

The most flights from YUL to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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

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 January 29, 2026.
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
7.9
Good
412 reviews

Crew

8.6

Boarding

8.2

Comfort

7.9

Entertainment

6.9

Food

7.5

Overall

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
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews

Crew

8.6

Boarding

8.2

Comfort

7.9

Entertainment

6.9

Food

7.5

Overall

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
10,667 reviews
Porter Airlines
7.9
Good
412 reviews

Crew

8.6

Boarding

8.2

Comfort

7.9

Entertainment

6.9

Food

7.5

Overall

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 2h 53m. Fly via Air Canada, United Airlines, 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?

    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 American Airlines and Porter 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 $148 and $149 on United Airlines and American 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: ANA (80%), Avianca (79%), Copa Airlines( 77%).

  • 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 $131. On average you can expect to pay $633. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for $195.

  • 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 $248). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$156Average$326FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$189Average$399FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$217Average$300FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$267Average$380FlexibilityNo cancel feeOn-time69%

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