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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago from C$ 195

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — CHI
31 May — 7 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Montreal Pierre Elliott Trudeau Intl to Chicago are usually found in January or March, booked 88 days in advance, depart on a Thursday or Saturday and return on a Friday

Cheap flight deals from Pierre Elliott Trudeau Intl to Chicago

Enter your travel dates to find the best prices.

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 1 May 2026.

Thu 4/66:30 a.m.
YUL
-
MDW
1 stop4h 05m
Porter Airlines
Sun 7/610:15 a.m.
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 29/4C$ 282
Thu 28/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 31/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 29/4C$ 312
Fri 12/66:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 14/610:15 a.m.
MDW
-
YUL
1 stop7h 00m
Porter Airlines
Deal found 30/4C$ 316
Thu 21/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 24/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 30/4C$ 319
Fri 22/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 24/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 29/4C$ 322
Fri 29/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Mon 1/63:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 28/4C$ 344
Tue 14/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Thu 23/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 28/4C$ 348
Thu 23/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Tue 28/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 29/4C$ 356
Sat 23/58:40 a.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Wed 27/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 26/4C$ 361
Fri 29/56:30 p.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 31/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 28/4C$ 366
Thu 18/68:45 a.m.
YUL
-
ORD
1 stop5h 25m
Air Canada
Sat 20/67:25 a.m.
ORD
-
YUL
1 stop5h 22m
Air Canada
Deal found 26/4C$ 368
Fri 22/56:30 p.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Mon 25/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 26/4C$ 371

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 1 May 2026.

Round-trip from

C$ 282

One-way from

C$ 195

Popular in

July

Cheapest in

January

Average price

C$ 370

Good round-trip deal

C$ 570 or less

Good one-way deal

C$ 380 or less
Porter Airlines
  • Porter Airlines
  • 4/6-7/6
  • 2 total stops
  • 10h 05m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/5
  • 1 total stop
  • 9h 05m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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).
Search Deals

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 1 May 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 26/6

10:35 a.m.-2:35 p.m.

1 stop5h 00m

Chicago Midway

Mon 6/7

10:25 a.m.-6:10 p.m.

1 stop6h 45m

C$ 383

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

12:49 p.m.-8:14 p.m.

1 stop8h 25m

Chicago O'Hare Intl

Sat 30/5

1:44 p.m.-11:13 p.m.

1 stop8h 29m

C$ 415

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 30/5

12:40 p.m.-8:24 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Mon 1/6

7:07 a.m.-5:43 p.m.

1 stop9h 36m

C$ 419

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 3/6

6:51 p.m.-12:08 a.m.

1 stop6h 17m

Chicago O'Hare Intl

Fri 5/6

2:59 p.m.-11:57 p.m.

1 stop7h 58m

C$ 419

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 18/5

7:00 a.m.-4:56 p.m.

1 stop10h 56m

Chicago O'Hare Intl

Thu 28/5

7:00 a.m.-4:15 p.m.

1 stop8h 15m

C$ 419

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 11/6

12:47 p.m.-4:26 p.m.

1 stop4h 39m

Chicago O'Hare Intl

Thu 18/6

1:46 p.m.-11:55 p.m.

1 stop9h 09m

C$ 419

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/6

6:00 a.m.-8:43 a.m.

1 stop3h 43m

Chicago Midway

Fri 5/6

5:08 p.m.-11:57 p.m.

1 stop5h 49m

C$ 419

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 18/6

6:00 a.m.-9:14 a.m.

1 stop4h 14m

Chicago Midway

Sat 20/6

9:17 a.m.-4:20 p.m.

1 stop6h 03m

C$ 419

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/6

12:48 p.m.-10:17 p.m.

1 stop10h 29m

Chicago Midway

Thu 18/6

12:45 p.m.-11:55 p.m.

1 stop10h 10m

C$ 419

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 8/6

12:48 p.m.-10:17 p.m.

1 stop10h 29m

Chicago Midway

Wed 10/6

1:21 p.m.-11:28 p.m.

1 stop9h 07m

C$ 419

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/4

Showing 1-10 of 40 resultsSorted by cheapest first
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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?

Booking 64 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, October is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of C$ 82). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in December is currently the most expensive (average of C$ 221). 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 1 May 2026.

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 66% versus a flight at noon.

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 1 May 2026.

The most flights from YUL to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (26 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 1 May 2026.
See what other customers who have flown with Porter Airlines,United Airlines, andWestJet 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
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,677 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,331 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,683 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,983 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 5h. Fly via Porter Airlines 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$ 175, 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$ 179 and C$ 247, respectively. These flights start at 55% 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: Japan Airlines (95%), Porter Airlines (89%), Qatar Airways (87%).

  • 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$ 267. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 378 on average, our data indicates C$ 683 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, October is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago (average of C$ 82). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago in December is currently the most expensive (average of C$ 221). 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 1 May 2026.
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 1 May 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 175AverageC$ 360FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 179AverageC$ 439FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 247AverageC$ 506FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 255AverageC$ 488FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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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.

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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