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$102+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YMQ
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Find cheap flights from Chicago to Montreal with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Montreal are usually found in September or January, booked 63 days in advance, depart on a Thursday or Saturday and return on a Friday

Cheap 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 January 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/315:45 amORD - YUL
1 stop18h 00mMultiple Airlines
Mon 1/511:25 amYUL - ORD
2 stops22h 06mMultiple Airlines
Deal found 12/29$623
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Tue 12/307:10 amORD - YUL
1 stop12h 05mMultiple Airlines
Thu 1/88:00 amYUL - ORD
1 stop13h 30mMultiple Airlines
Deal found 12/29$668
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/315:45 amORD - YUL
1 stop18h 00mMultiple Airlines
Wed 1/74:35 pmYUL - ORD
2 stops28h 55mMultiple Airlines
Deal found 12/30$702
This FlightHub deal was found by Cheapflights users on 12/29. 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.
Wed 12/3111:00 amMDW - YUL
1 stop5h 15mPorter Airlines
Mon 1/56:45 amYUL - MDW
1 stop4h 25mPorter Airlines
Deal found 12/29$770
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/3111:00 amMDW - YUL
1 stop5h 15mMultiple Airlines
Wed 1/72:40 pmYUL - MDW
1 stop23h 29mMultiple Airlines
Deal found 12/30$789
This Air Canada deal was found by Cheapflights users on 12/29. 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.
Tue 12/305:52 pmORD - YUL
Nonstop2h 25mAir Canada
Thu 1/86:25 pmYUL - ORD
Nonstop2h 45mAir Canada
Deal found 12/29$812
This American Airlines deal was found by Cheapflights users on 12/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:55 amORD - YUL
Nonstop2h 15mAmerican Airlines
Wed 1/77:30 amYUL - ORD
1 stop10h 16mAmerican Airlines
Deal found 12/30$822
This FlightHub deal was found by Cheapflights users on 12/31. 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.
Wed 12/3111:00 amMDW - YUL
1 stop5h 15mPorter Airlines
Thu 1/111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Deal found 12/31$854
This Kiwi.com deal was found by Cheapflights users on 12/31. 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.
Wed 12/317:10 amORD - YUL
1 stop16h 35mMultiple Airlines
Sun 1/42:30 pmYUL - ORD
2 stops23h 27mMultiple Airlines
Deal found 12/31$860
This FlightHub deal was found by Cheapflights users on 12/30. 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.
Tue 12/304:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Mon 1/58:55 amYUL - MDW
1 stop7h 25mPorter Airlines
Deal found 12/30$933
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/319:50 amMDW - YUL
1 stop13h 09mWestJet
Wed 1/76:45 amYUL - MDW
2 stops7h 03mWestJet
Deal found 12/30$938
This oojo deal was found by Cheapflights users on 12/31. 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.
Wed 12/3111:00 amMDW - YUL
1 stop5h 15mPorter Airlines
Sun 1/410:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 12/31$1,039

Find 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 January 1, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$198
(American Airlines)

One-way from

$102
(Air Canada)

Popular in

December

Cheapest in

September

Average price

$323

Good round-trip deal

$509 or less

Good one-way deal

$442 or less
Provider with most accurate pricing for Chicago (CHI)-Montreal (YMQ) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montreal (YMQ) flights.
Search Deals
From Chicago (CHI) to Montreal (YMQ)
Search Deals
One-way flight from Chicago (CHI) to Montreal (YMQ)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Montreal (YMQ).
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Montreal (YMQ).
Search Deals

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 January 1, 2026.
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

Wed 2/4

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

6:45 am-10:05 am

1 stop4h 20m

$217

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 1/29

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

6:45 am-10:05 am

1 stop4h 20m

$235

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/5

10:48 am-4:55 pm

1 stop5h 07m

Montreal Pierre Elliott Trudeau Intl

Sat 2/7

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 2/17

12:45 pm-11:45 pm

1 stop10h 00m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

7:00 am-3:21 pm

1 stop9h 21m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 2/14

1:29 pm-11:10 pm

1 stop8h 41m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 2/7

4:30 pm-11:50 pm

1 stop6h 20m

Montreal Pierre Elliott Trudeau Intl

Wed 2/11

7:00 am-11:59 am

1 stop5h 59m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 2/16

1:26 pm-11:26 pm

1 stop9h 00m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/5

10:48 am-4:55 pm

1 stop5h 07m

Montreal Pierre Elliott Trudeau Intl

Wed 2/11

12:54 pm-5:55 pm

1 stop6h 01m

$237

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 2/15

1:29 pm-11:10 pm

1 stop8h 41m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 2/12

9:48 am-4:53 pm

1 stop6h 05m

Montreal Pierre Elliott Trudeau Intl

Fri 2/20

2:40 pm-9:30 pm

1 stop7h 50m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 38 results
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Compare providers for flights from Chicago to Montreal

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Montreal in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Montreal flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Montreal flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Montreal flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Montreal flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-Montreal 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 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 December 26, 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, April is the cheapest month in which you can book a flight from Chicago to Montreal (average of $104). Flying from Chicago to Montreal in July is currently the most expensive (average of $283). 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 January 1, 2026.

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 evening tend to be the most expensive. A flight at noon could potentially save you up to 22% 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 January 1, 2026.

The most flights from CHI to YMQ are scheduled on a Wednesday (22 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Chicago to Montreal?

What’s the top layover airport for flights from Chicago to Montreal?

Share of 1-stop round-trip flights from Chicago to Montreal chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YTZ) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Montreal on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Montreal?

Average round-trip fare for 1-stop flights from Chicago to Montreal, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YTZ) is the most affordable 1-stop option, with an average round-trip price of $278.

What’s the fastest layover option from Chicago to Montreal?

Shortest average travel time for 1-stop one-way flights from Chicago to Montreal, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 3h 55m.

Which airport typically offers the quickest layover for flights from Chicago to Montreal?

Average layover duration for 1-stop one-way flights from Chicago to Montreal, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YTZ) offer the fastest connection on this route, with an average layover time of 0h 59m.

How often are flights from Chicago to Montreal delayed?

About 15% of weekly flights between Chicago and Montreal have experienced delays in the past year, with the average delay time being 135 minutes.

What is the most punctual flight time for Chicago to Montreal flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Montreal flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.

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 January 1, 2026.
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
8.0
Very good
403 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
8.0
Very good
403 reviews
Porter Airlines
8.0
Very good
403 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
United Airlines
7.4
Good
9,131 reviews
Porter Airlines
8.0
Very good
403 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
American Airlines
7.2
Good
11,071 reviews
Porter Airlines
8.0
Very good
403 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
10,571 reviews
Porter Airlines
8.0
Very good
403 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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 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 4h 30m. Fly via Porter Airlines or Delta to get the fastest option. Chicago and Montreal are separated by a distance of 743 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 $126, United Airlines will fly you from Chicago to Montreal and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and American Airlines - these airlines can fly you to your destination from $152 and $192, respectively. United Airlines is 64% 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 Air Canada. According to our data, you can fly for as low as $64. Users have also found prices from $74 and $74 on American Airlines and United 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 (80%), Porter Airlines (79%), Japan Airlines (76%).

  • What are the cheapest flights from Chicago to Montreal?

    While on average a flight from Chicago to Montreal is generally $1,063, our data shows the cheapest flight currently is $148. When looking at the most popular route, (Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl), you can expect to pay $197 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, April is the cheapest month in which you can book a flight from Chicago to Montreal (average of $104). Flying from Chicago to Montreal in July is currently the most expensive (average of $283). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Chicago to Montreal

Discover the top 3 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$156Average$355FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$168Average$405FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$192Average$405FlexibilityNo cancel feeOn-time71%

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