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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 176

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Montreal Pierre Elliott Trudeau Intl to Chicago are usually found in June or September, booked 77 days in advance, depart on a Friday or Saturday 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 11 September 2025.

Round-trip from

C$ 290

One-way from

C$ 176

Popular in

December

Cheapest in

June

Average price

C$ 424

Good round-trip deal

C$ 518 or less

Good one-way deal

C$ 461 or less
Porter Airlines
  • Porter Airlines
  • 9/11-11/11
  • 2 total stops
  • 8h 50m total
  • Montreal to Chicago
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Air Canada
  • Air Canada
  • 2/11
  • Nonstop
  • 2h 53m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 23 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 11 September 2025.

Sun 9/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 11/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 8/9C$ 290
Fri 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 20/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9C$ 291
Fri 21/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Fri 28/1111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/9C$ 292
Tue 7/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Wed 15/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 9/9C$ 297
Tue 7/1010:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Fri 24/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9C$ 298
Thu 20/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Thu 27/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 10/9C$ 299
Wed 8/1010:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Sun 12/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 10/9C$ 302
Sun 16/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Tue 18/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 8/9C$ 306
Wed 19/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 9/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/9C$ 309
Sun 9/119:25 a.m.YUL - ORD
Nonstop2h 53mAir Canada
Tue 11/1112:50 p.m.ORD - YUL
Nonstop2h 07mAir Canada
Deal found 8/9C$ 317
Thu 16/108:20 a.m.YUL - ORD
Nonstop2h 31mAir Canada
Sun 19/108:40 a.m.ORD - YUL
Nonstop2h 14mAir Canada
Deal found 9/9C$ 320
Tue 7/108:20 a.m.YUL - ORD
Nonstop2h 31mAir Canada
Sun 12/108:40 a.m.ORD - YUL
Nonstop2h 14mAir Canada
Deal found 9/9C$ 324

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 11 September 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 2/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Mon 6/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 298

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 21/11

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

1 stop4h 55m

Chicago Midway

Mon 24/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 315

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 5/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 327

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Mon 20/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 328

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 8/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Thu 9/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 330

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Tue 21/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Wed 22/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 31/10

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

1 stop4h 20m

Chicago Midway

Sun 2/11

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 333

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/11

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

1 stop4h 20m

Chicago Midway

Thu 27/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 334

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 13/10

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Wed 15/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 45 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 29 August 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, January is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of C$ 261). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of C$ 349). 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 11 September 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 afternoon, which can drop the price by up to 26% 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 Sunday 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 11 September 2025.

The most flights from YUL to CHI are scheduled on a Wednesday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 11 September 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
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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.
United Airlines
7.4
Good
8,937 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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.
WestJet
7.2
Good
3,091 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

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 6h 39m. Fly via Porter Airlines, Air Canada, or Delta to get the fastest option. The distance between Montreal Pierre Elliott Trudeau Intl Airport and Chicago is about 1196 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$ 178, 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$ 197 and C$ 262, respectively. These flights start at 60% lower than the current average price 3 months from now.

  • 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: Qantas Airways (90%), Qatar Airways (90%), Emirates (90%).

  • 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$ 250. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 346 on average, our data indicates C$ 1,433 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, January is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of C$ 261). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in March is currently the most expensive (average of C$ 349). 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 11 September 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 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 629,999 searches. Data last updated 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 178AverageC$ 414FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 197AverageC$ 446FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 262AverageC$ 524FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 357AverageC$ 490FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 454AverageC$ 598FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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

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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.

Can Cheapflights notify me if prices for flights from Pierre Elliott Trudeau Intl to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Pierre Elliott Trudeau Intl to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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