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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 227

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 25/11. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

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 Thursday or Friday and return on a Wednesday

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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 28 October 2025.

Thu 11/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 15/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 27/10C$ 368
Thu 20/116:15 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Mon 24/117:05 a.m.ORD - YUL
Nonstop2h 05mAir Canada
Deal found 28/10C$ 369
Fri 12/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 19/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 28/10C$ 369
Tue 9/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 12/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 26/10C$ 371
Mon 17/112:00 p.m.YUL - ORD
1 stop6h 30mAir Canada
Sun 23/118:00 a.m.ORD - YUL
1 stop4h 22mAir Canada
Deal found 27/10C$ 375
Thu 18/1210:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Mon 12/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 28/10C$ 375
Sat 22/118:55 a.m.YUL - MDW
1 stop3h 55mPorter Airlines
Sat 29/1112:45 p.m.MDW - YUL
1 stop5h 05mPorter Airlines
Deal found 28/10C$ 378
Thu 11/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 18/1211:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 27/10C$ 380
Sat 22/116:15 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Mon 24/117:05 a.m.ORD - YUL
Nonstop2h 05mAir Canada
Deal found 27/10C$ 382
Tue 25/116:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Tue 2/1210:38 a.m.ORD - YUL
Nonstop2h 22mUnited Airlines
Deal found 27/10C$ 383
Thu 4/1210:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Sun 7/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 26/10C$ 385
Mon 24/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 29/1112:45 p.m.MDW - YUL
1 stop5h 05mPorter Airlines
Deal found 25/10C$ 386

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 28 October 2025.

Round-trip from

C$ 315

One-way from

C$ 227

Popular in

October

Cheapest in

September

Average price

C$ 554

Good round-trip deal

C$ 618 or less

Good one-way deal

C$ 327 or less
United Airlines
  • United Airlines
  • 4/4-8/4
  • 1 total stop
  • 7h 32m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 25/11
  • 1 total stop
  • 4h 20m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 629,999 searches. Data last updated 28 October 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

Sat 4/4

9:25 a.m.-10:57 a.m.

Nonstop2h 32m

Chicago O'Hare Intl

Wed 8/4

9:00 a.m.-4:21 p.m.

1 stop6h 21m

C$ 315

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 2/3

3:11 p.m.-7:48 p.m.

1 stop5h 37m

Chicago O'Hare Intl

Mon 9/3

7:00 a.m.-5:55 p.m.

1 stop9h 55m

C$ 322

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 27/2

8:00 p.m.-7:50 a.m.

1 stop12h 50m

Chicago O'Hare Intl

Sun 8/3

9:01 p.m.-7:45 a.m.

1 stop9h 44m

C$ 324

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 a.m.-9:35 a.m.

1 stop4h 35m

Chicago O'Hare Intl

Wed 8/4

7:10 a.m.-5:04 p.m.

1 stop8h 54m

C$ 358

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 20/3

7:00 a.m.-2:33 p.m.

1 stop8h 33m

Chicago O'Hare Intl

Mon 23/3

8:15 p.m.-1:53 a.m.

1 stop4h 38m

C$ 369

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/1

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Fri 16/1

11:00 a.m.-7:15 p.m.

1 stop7h 15m

C$ 375

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 30/12

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Sat 3/1

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 375

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 22/11

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Sat 29/11

12:45 p.m.-6:50 p.m.

1 stop5h 05m

C$ 378

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 25/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Tue 2/12

10:38 a.m.-2:00 p.m.

Nonstop2h 22m

C$ 383

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 2/3

12:45 p.m.-9:46 p.m.

1 stop10h 01m

Chicago Midway

Mon 9/3

2:00 p.m.-11:39 p.m.

1 stop8h 39m

C$ 385

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 37 results
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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 24 October 2025.

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 C$ 183). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of C$ 358). 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 28 October 2025.

When flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 52% versus 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 16 December 2024.

Travelers seeking maximum savings on their Montreal Pierre Elliott Trudeau Intl Airport to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday evenings 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 28 October 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?

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 28 October 2025.
See what other customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Montreal Pierre Elliott Trudeau Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

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
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,996 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,033 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

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.
WestJet
7.2
Good
3,148 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

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
10,370 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

8.0

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, Porter Airlines, or Delta to get the fastest option. The distance between Montreal Pierre Elliott Trudeau Intl Airport and Chicago is about 1199 km. 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?

    Currently priced at C$ 180, American Airlines will fly you from Montreal Pierre Elliott Trudeau Intl Airport to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Porter Airlines and Air Canada - these airlines can fly you to your destination from C$ 199 and C$ 262, respectively. These flights start at 60% lower than the current average price 3 months from now.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as C$ 228. However, be on the lookout for offers from Air Canada and Porter Airlines, as they are both options that can get you from Montreal Pierre Elliott Trudeau Intl Airport to Chicago for a low price.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Montreal Pierre Elliott Trudeau Intl Airport to Chicago on time: Qatar Airways (97%), Qantas Airways (95%), Emirates (93%).

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

    Looking at all options, your cheapest flight can be booked for C$ 235. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 255 on average, our data indicates C$ 1,406 when flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago.

  • 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 C$ 183). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of C$ 358). 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

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Fly from Pierre Elliott Trudeau Intl to Chicago on these airlines

Choose from the following airlines for your flight from Pierre Elliott Trudeau Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 28 October 2025.
Air Canada flights from Montreal Pierre Elliott Trudeau Intl to Chicago
Porter Airlines flights from Montreal Pierre Elliott Trudeau Intl to Chicago
United Airlines flights from Montreal Pierre Elliott Trudeau Intl to Chicago

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 629,999 searches. Data last updated 28 October 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 180AverageC$ 457FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 199AverageC$ 502FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 262AverageC$ 521FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 375AverageC$ 509FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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How does Cheapflights help users find flights from Pierre Elliott Trudeau Intl to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Pierre Elliott Trudeau Intl to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Pierre Elliott Trudeau Intl to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Pierre Elliott Trudeau Intl to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Pierre Elliott Trudeau Intl to Chicago flexibly with Cheapflights today.

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