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Cheap flights from Montreal to Chicago from C$ 243

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
14 Jul — 21 Jul1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Montreal to Chicago are usually found in April or March, booked 67 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap flight deals from Montreal to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Montreal to Chicago
Explore the most affordable flight options available from Montreal to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 June 2026.

Fri 4/98:40 a.m.
YUL
-
ORD
2 stops5h 42m
Multiple Airlines
Tue 8/93:20 p.m.
ORD
-
YUL
1 stop3h 50m
Multiple Airlines
Deal found 11/6C$ 407
Fri 24/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Mon 27/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 12/6C$ 407
Sat 27/611:10 a.m.
YUL
-
ORD
1 stop4h 45m
Air Canada
Wed 1/77:25 a.m.
ORD
-
YUL
1 stop5h 22m
Air Canada
Deal found 11/6C$ 408
Thu 23/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Tue 28/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 14/6C$ 408
Thu 3/99:45 a.m.
YUL
-
ORD
Nonstop2h 36m
United Airlines
Sun 6/98:45 a.m.
ORD
-
YUL
1 stop4h 55m
United Airlines
Deal found 10/6C$ 410
Fri 4/96:00 a.m.
YUL
-
MDW
1 stop4h 17m
Delta
Tue 8/95:59 p.m.
MDW
-
YUL
1 stop4h 11m
Delta
Deal found 12/6C$ 410
Fri 4/96:00 a.m.
YUL
-
ORD
1 stop8h 08m
Delta
Mon 7/97:00 a.m.
ORD
-
YUL
1 stop8h 20m
Delta
Deal found 10/6C$ 411
Thu 25/68:45 a.m.
YUL
-
ORD
1 stop5h 34m
Air Canada
Mon 29/68:35 a.m.
ORD
-
YUL
Nonstop2h 23m
Air Canada
Deal found 11/6C$ 413
Tue 4/810:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 9/810:20 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 11/6C$ 413
Tue 21/74:30 p.m.
YUL
-
ORD
1 stop4h 59m
Air Canada
Mon 27/72:00 p.m.
ORD
-
YUL
1 stop4h 47m
Air Canada
Deal found 12/6C$ 414
Tue 21/76:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Thu 30/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 12/6C$ 414
Thu 25/66:10 a.m.
YUL
-
ORD
Nonstop2h 40m
United Airlines
Tue 30/66:30 a.m.
ORD
-
YUL
1 stop12h 15m
United Airlines
Deal found 11/6C$ 415

Find flight deals from Montreal to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Montreal (YMQ) 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 14 June 2026.

Round-trip from

C$ 407

One-way from

C$ 243

Popular in

July

Cheapest in

April

Average price

C$ 477

Good round-trip deal

C$ 532 or less

Good one-way deal

C$ 384 or less
Porter Airlines
  • Porter Airlines
  • 4/9-8/9
  • 3 total stops
  • 9h 32m total
  • Montreal to Chicago
Search Deals
Air Canada
  • Air Canada
  • 9/8
  • 2 total stops
  • 5h 39m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Montreal (YMQ) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Montreal (YMQ) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montreal 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 14 June 2026.
Use the filters below to find and compare flights from Montreal 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

Tue 20/10

6:00 a.m.-12:33 p.m.

1 stop7h 33m

Chicago Midway

Tue 27/10

9:30 a.m.-3:59 p.m.

1 stop5h 29m

C$ 410

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 24/7

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

1 stop5h 00m

Chicago Midway

Mon 27/7

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

1 stop6h 45m

C$ 415

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 30/6

2:20 p.m.-11:31 p.m.

1 stop10h 11m

Chicago O'Hare Intl

Tue 7/7

8:45 a.m.-12:00 p.m.

Nonstop2h 15m

C$ 422

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 30/6

2:40 p.m.-10:48 p.m.

1 stop9h 08m

Chicago O'Hare Intl

Wed 8/7

2:07 p.m.-11:25 p.m.

1 stop8h 18m

C$ 422

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 13/7

6:00 a.m.-9:13 a.m.

1 stop4h 13m

Chicago Midway

Mon 20/7

1:18 p.m.-11:25 p.m.

1 stop9h 07m

C$ 422

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 29/6

6:00 a.m.-1:04 p.m.

1 stop8h 04m

Chicago O'Hare Intl

Fri 3/7

1:40 p.m.-11:28 p.m.

1 stop8h 48m

C$ 424

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 27/6

6:00 a.m.-1:08 p.m.

1 stop8h 08m

Chicago O'Hare Intl

Sun 28/6

3:45 p.m.-11:22 p.m.

1 stop6h 37m

C$ 436

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 25/6

12:47 p.m.-8:31 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Mon 6/7

5:22 p.m.-11:28 p.m.

1 stop5h 06m

C$ 457

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 25/6

5:07 p.m.-8:31 p.m.

1 stop4h 24m

Chicago O'Hare Intl

Mon 29/6

7:01 a.m.-4:11 p.m.

1 stop8h 10m

C$ 457

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 21/7

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Sat 25/7

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

1 stop6h 45m

C$ 460

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 43 resultsSorted by cheapest first
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Best time to book a flight from Montreal to Chicago

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

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

Currently, February is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 71). Flying from Montreal to Chicago in January is currently the most expensive (average of C$ 187). 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 YMQ to CHI?

Find hourly flight availability from Montreal 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 14 June 2026.

It’s optimal to fly from Montreal to Chicago in the evening. By choosing this option you can save up to 66% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Montreal to Chicago

Explore weekly flight availability from Montreal 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 14 June 2026.

The most flights from YMQ to CHI are scheduled on a Wednesday (33 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 on average).

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

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

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

Toronto (YTZ) – chosen by Cheapflights users on 90% of one-stop itineraries from Montreal to Chicago on Cheapflights.

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

Average round-trip fare for 1-stop flights from Montreal to Chicago, 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 C$ 298.

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

Shortest average travel time for 1-stop one-way flights from Montreal to Chicago, 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: 4h 19m.

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

Average layover duration for 1-stop one-way flights from Montreal to Chicago, 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 1h 16m.

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

The price you pay for your flight from Montreal to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 87 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 14 June 2026.
Read through reviews of airlines operating flights from Montreal to Chicago, such as Porter Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
United Airlines
7.4
Good
9,828 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
American Airlines
7.1
Good
11,661 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,194 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Related info for your journey

Find useful and relevant information for your journey from Montreal 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 to Chicago?

    Airlines like Delta and Porter Airlines fly from Montreal to Chicago in about 5h. The time it takes to get you to your destination can typically vary by up to 2h 33m. Montreal and Chicago are separated by a distance of 1196 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    Currently priced at C$ 180, American Airlines will fly you from Montreal 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 United Airlines - these airlines can fly you to your destination from C$ 205 and C$ 261, respectively. You may be able to fly from Montreal to Chicago for 59% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Montreal 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 to Chicago on time: Emirates (94%), ANA (93%), Finnair (91%).

  • What are the cheapest flights from Montreal to Chicago?

    Looking for the cheapest flight from Montreal to Chicago? While on average our users pay C$ 1,328, our data indicates the cheapest price to be C$ 263. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 338.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Montreal 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 to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 71). Flying from Montreal to Chicago in January is currently the most expensive (average of C$ 187). 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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Fly from Montreal to Chicago on these airlines

Choose from the following airlines for your flight from Montreal to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 14 June 2026.
Air Canada flights from Montreal to Chicago
Porter Airlines flights from Montreal to Chicago
United Airlines flights from Montreal to Chicago

Top 4 airlines flying from Montreal to Chicago

Discover the top 4 airlines that operate flights from Montreal 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 14 June 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 180AverageC$ 376FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 205AverageC$ 430FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 261AverageC$ 485FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 263AverageC$ 561FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Montreal to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Montreal to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Montreal to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Montreal.

Can Cheapflights find flights from Montreal to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Montreal shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Montreal to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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