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$61+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YMQ
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Mon 1/511:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Deal found 12/21$509
This FlightHub deal was found by Cheapflights users on 12/21. 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 1/511:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Deal found 12/21$514
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/313:10 pmMDW - YUL
1 stop8h 20mMultiple Airlines
Wed 1/74:35 pmYUL - MDW
2 stops19h 56mMultiple Airlines
Deal found 12/21$530
This Trip.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/2911:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Fri 1/26:45 amYUL - MDW
1 stop4h 25mPorter Airlines
Deal found 12/22$534
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/294:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Wed 12/316:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/21$535
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/3111:23 amORD - YUL
1 stop12h 07mMultiple Airlines
Tue 1/65:25 pmYUL - ORD
2 stops21h 56mMultiple Airlines
Deal found 12/21$545
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/306:50 amORD - YUL
2 stops40h 40mMultiple Airlines
Wed 1/74:35 pmYUL - ORD
1 stop27h 42mMultiple Airlines
Deal found 12/21$546
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Fri 1/26:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/21$547
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:52 pmORD - YUL
Nonstop2h 25mUnited Airlines
Wed 1/74:45 pmYUL - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/21$554
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:24 pmORD - YUL
1 stop5h 24mUnited Airlines
Wed 1/74:45 pmYUL - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/21$563
This Air Canada deal was found by Cheapflights users on 12/21. 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.
Wed 12/3112:50 pmORD - YUL
Nonstop2h 07mAir Canada
Tue 1/610:10 amYUL - ORD
1 stop6h 00mAir Canada
Deal found 12/21$565
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:52 pmORD - YUL
Nonstop2h 25mUnited Airlines
Tue 1/63:00 pmYUL - ORD
1 stop6h 13mUnited Airlines
Deal found 12/21$569

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$192
(American Airlines)

One-way from

$61
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$412

Good round-trip deal

$524 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 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

Wed 2/18

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Fri 2/20

6:45 am-10:05 am

1 stop4h 20m

$203

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/19

11:05 am-5:45 pm

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

6:45 am-10:10 am

1 stop4h 25m

$203

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/26

11:00 am-6:45 pm

1 stop6h 45m

Montreal Pierre Elliott Trudeau Intl

Wed 3/4

6:45 am-10:05 am

1 stop4h 20m

$222

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

Thu 2/12

6:00 am-4:53 pm

1 stop9h 53m

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Tue 2/17

6:45 am-4:53 pm

1 stop9h 08m

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

6:00 pm-11:56 pm

1 stop6h 56m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Fri 2/20

6:15 am-1:40 pm

1 stop6h 25m

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

6:00 am-1:20 pm

1 stop8h 20m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sat 2/14

6:15 am-1:40 pm

1 stop6h 25m

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:00 am-9:41 am

1 stop4h 41m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sat 2/21

6:30 am-11:59 am

1 stop4h 29m

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

7:00 am-4:51 pm

1 stop10h 51m

$237

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Wed 2/18

5:25 am-4:53 pm

1 stop10h 28m

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

6:00 am-9:41 am

1 stop4h 41m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 December.
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 19, 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 $103). 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 December 23, 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 evening tend to be the most expensive. A flight in the morning could potentially save you up to 29% 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 December 23, 2025.

The most flights from CHI to YMQ are scheduled on a Tuesday (22 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 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 December 23, 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
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

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
9,106 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

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
11,050 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

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
10,551 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

Food

7.6

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 $147 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 $1,074, our data shows the cheapest flight currently is $185. When looking at the most popular route, (Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl), you can expect to pay $191 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 $103). 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 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$148Average$367FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$164Average$398FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$192Average$405FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$249Average$457FlexibilityNo cancel feeOn-time52%

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