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$101+ Cheap flights from Chicago (CHI) to Montreal (YMQ)

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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YMQ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Montreal are usually found in September or October, booked 63 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Chicago to Montreal

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Montreal (YMQ). 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 September 11, 2025.

Round-trip from

$232
(Kiwi.com)

One-way from

$101
(iWofly)

Popular in

December

Cheapest in

September

Average price

$310

Good round-trip deal

$453 or less

Good one-way deal

$177 or less
From Chicago (CHI) to Montreal (YMQ)
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One-way flight from Chicago (CHI) to Montreal (YMQ)
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Highest demand for flights based on searches. 3% potential increase in price ($12 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 September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Montreal (YMQ).
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Price to beat on a one-way flight from Chicago (CHI) to Montreal (YMQ).
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Find flight deals from Chicago to Montreal

Cheapest flights from Chicago to Montreal
Explore the most affordable flight options available from Chicago to Montreal. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/235:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Mon 10/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$232
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/245:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Sun 10/266:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$235
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Tue 10/75:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Tue 10/1410:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Deal found 9/9$238
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 12/44:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Tue 12/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$240
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 10/209:35 amMDW - YUL
1 stop5h 25mPorter Airlines
Thu 10/231:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$242
This Flightnetwork deal was found by Cheapflights users on 9/9. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:40 amORD - YUL
Nonstop2h 14mAir Canada
Mon 10/279:25 amYUL - ORD
Nonstop2h 53mAir Canada
Deal found 9/9$247
This Trip.com deal was found by Cheapflights users on 9/9. 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 10/95:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Tue 10/1410:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Deal found 9/9$253
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:40 amORD - YUL
Nonstop2h 14mAir Canada
Fri 10/319:25 amYUL - ORD
Nonstop2h 53mAir Canada
Deal found 9/9$253
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Mon 11/1710:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 9/9$256
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/189:35 amMDW - YUL
1 stop7h 20mPorter Airlines
Tue 10/211:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$259
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/119:35 amMDW - YUL
1 stop7h 20mPorter Airlines
Wed 10/151:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$260
This Air Canada deal was found by Cheapflights users on 9/9. 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.
Fri 12/57:15 amORD - YUL
Nonstop2h 05mAir Canada
Fri 12/51:10 pmYUL - ORD
1 stop7h 20mAir Canada
Deal found 9/9$261

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Montreal 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Montreal that are best for you.

Fly from

Chicago

Fly to

Montreal

Route

Depart

Return

Price

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 10/23

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Mon 10/27

11:25 am-3:20 pm

1 stop4h 55m

$234

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 10/7

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Tue 10/14

10:45 am-4:24 pm

1 stop6h 39m

$238

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/18

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Tue 10/21

1:10 pm-4:24 pm

1 stop4h 14m

$259

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/18

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Wed 10/22

10:45 am-4:24 pm

1 stop6h 39m

$260

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/11

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Tue 10/14

10:45 am-4:24 pm

1 stop6h 39m

$260

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 10/23

9:35 am-4:00 pm

1 stop5h 25m

Montreal Pierre Elliott Trudeau Intl

Sun 10/26

6:45 am-10:05 am

1 stop4h 20m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 10/12

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Wed 10/15

1:10 pm-4:24 pm

1 stop4h 14m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 10/30

4:15 pm-10:45 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 11/2

5:45 am-9:05 am

1 stop4h 20m

$265

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 10/20

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Thu 10/23

10:45 am-4:24 pm

1 stop6h 39m

$265

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 12/3

11:00 am-5:45 pm

1 stop5h 45m

Montreal Pierre Elliott Trudeau Intl

Thu 12/11

6:45 am-10:05 am

1 stop4h 20m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Montreal

Have a flexible travel schedule? Discover the best time to fly to Montreal from Chicago 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 Chicago to Montreal

How far ahead should I book a flight from Chicago to Montreal?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Montreal. Price data was last updated on August 29, 2025.

The price you pay for your flight from Chicago to Montreal may vary depending on when you book. For the best chance of a lower fare, look to book 63 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Montreal?

Currently, January is the cheapest month in which you can book a flight from Chicago to Montreal (average of $270). Flying from Chicago to Montreal in July is currently the most expensive (average of $409). 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 CHI to YMQ?

Find hourly flight availability from Chicago to Montreal. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Chicago to Montreal is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 27% on airfare.

Weekly flight availability from Chicago to Montreal

Explore weekly flight availability from Chicago to Montreal. 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 September 11, 2025.

The most flights from CHI to YMQ are scheduled on a Wednesday (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 Chicago to Montreal?

Reviews of airlines servicing Montreal

Get insights into the airlines that provide service to Montreal. 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 Montreal. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Porter Airlines, United Airlines, and American Airlines from Chicago to Montreal. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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

Boarding

8.1

Overall

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Comfort

7.9

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 Chicago to Montreal. 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 Chicago to Montreal?

    There are many flights that can get you from Chicago to Montreal in 2h 29m. Fly via Porter Airlines, United Airlines, or Delta to get the fastest option. Chicago and Montreal are separated by a distance of 745 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Montreal round-trip?

    Currently priced at $162, Air Canada will fly you from Chicago to Montreal and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and United Airlines - these airlines can fly you to your destination from $192 and $215, respectively. Air Canada is 56% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Montreal one-way?

    For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as $101. Users have also found prices from $115 and $115 on Air Canada and American Airlines, respectively.

  • What are the most reliable airlines from Chicago to Montreal?

    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 Chicago to Montreal on time: Republic Airways (82%), Alaska Airlines (82%), Copa Airlines (77%).

  • What are the cheapest flights from Chicago to Montreal?

    While on average a flight from Chicago to Montreal is generally $773, our data shows the cheapest flight currently is $74. When looking at the most popular route, (Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl), you can expect to pay $274 for that flight.

  • Can I find deals for flights from Chicago to Montreal that include hotel bookings?

    Yes. In addition to deals on Chicago to Montreal flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Montreal?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Montreal.

  • Can I find deals for business class flights from Chicago to Montreal?

    Yes. Cheapflights offers flight deals from Chicago to Montreal 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 Chicago to Montreal?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Montreal (average of $270). Flying from Chicago to Montreal in July is currently the most expensive (average of $409). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Chicago to Montreal

Discover the top 4 airlines that operate flights from Chicago to Montreal. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$162Average$396FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$192Average$405FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$215Average$379FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$245Average$391FlexibilityNo cancel feeOn-time52%

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