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Cheap flights from Montreal to Chicago from C$ 231

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 27/11. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Montreal to Chicago are usually found in September or March, booked 67 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap 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 3 November 2025.

Round-trip from

C$ 324

One-way from

C$ 231

Popular in

November

Cheapest in

September

Average price

C$ 542

Good round-trip deal

C$ 606 or less

Good one-way deal

C$ 306 or less
Air Canada
  • Air Canada
  • 24/2-3/3
  • 1 total stop
  • 7h 05m total
  • Montreal to Chicago
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Air Canada
  • Air Canada
  • 3/12
  • Nonstop
  • 2h 53m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Montreal (YMQ) to Chicago (CHI).
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Price to beat on a one-way flight from Montreal (YMQ) to Chicago (CHI).
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Find 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 3 November 2025.

Thu 4/129:25 a.m.YUL - ORD
Nonstop2h 53mAir Canada
Sun 7/1212:50 p.m.ORD - YUL
Nonstop2h 07mAir Canada
Deal found 3/11C$ 343
Fri 21/116:15 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Mon 24/117:05 a.m.ORD - YUL
Nonstop2h 05mAir Canada
Deal found 31/10C$ 346
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 1/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 2/11C$ 360
Fri 19/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Sun 21/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 367
Thu 18/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 1/11C$ 368
Fri 5/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 8/1211:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 2/11C$ 370
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 1/11C$ 371
Fri 19/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 377
Fri 28/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 2/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 2/11C$ 378
Sun 23/119:25 a.m.YUL - ORD
Nonstop2h 53mAir Canada
Mon 24/117:05 a.m.ORD - YUL
Nonstop2h 05mAir Canada
Deal found 1/11C$ 382
Mon 15/129:25 a.m.YUL - ORD
Nonstop2h 53mAir Canada
Thu 1/112:50 p.m.ORD - YUL
Nonstop2h 07mAir Canada
Deal found 2/11C$ 384
Thu 4/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 7/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 384

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 3 November 2025.
Use the filters below to find and compare flights from Montreal to Chicago that are best for you.

Fly from

Montreal

Fly to

Chicago

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 a.m.-9:35 a.m.

1 stop4h 35m

Chicago O'Hare Intl

Wed 8/4

5:50 a.m.-5:04 p.m.

1 stop10h 14m

C$ 326

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 26/2

12:45 p.m.-6:57 p.m.

1 stop7h 12m

Chicago O'Hare Intl

Mon 2/3

7:00 a.m.-4:01 p.m.

1 stop8h 01m

C$ 326

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 15/1

9:25 a.m.-11:06 a.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sun 18/1

8:00 a.m.-2:22 p.m.

1 stop5h 22m

C$ 347

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 a.m.-9:35 a.m.

1 stop4h 35m

Chicago O'Hare Intl

Tue 7/4

7:10 a.m.-5:04 p.m.

1 stop8h 54m

C$ 357

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/12

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 8/12

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 370

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 16/12

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 4/1

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 377

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 16/12

1:10 p.m.-2:55 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

7:05 a.m.-10:10 a.m.

Nonstop2h 05m

C$ 384

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 15/12

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sat 3/1

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 394

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 27/11

2:00 p.m.-7:30 p.m.

1 stop6h 30m

Chicago O'Hare Intl

Sun 30/11

8:00 a.m.-1:22 p.m.

1 stop4h 22m

C$ 396

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 21/12

6:25 p.m.-8:10 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Sat 27/12

8:15 p.m.-1:53 a.m.

1 stop4h 38m

C$ 399

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 41 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Montreal to Chicago. Price data was last updated on 31 October 2025.

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 67 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 Montreal to Chicago?

Currently, September is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 184). Flying from Montreal to Chicago in March is currently the most expensive (average of C$ 359). 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 3 November 2025.

It’s optimal to fly from Montreal to Chicago in the evening. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Montreal to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Montreal to Chicago. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Montreal to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 3 November 2025.

The most flights from YMQ to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Montreal 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 3 November 2025.
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
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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
8,997 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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
11,036 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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
3,153 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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
10,394 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

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 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, Air Canada, and Porter Airlines fly from Montreal to Chicago in about 2h 41m. The time it takes to get you to your destination can typically vary by up to 2h 14m. Montreal and Chicago are separated by a distance of 1199 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$ 199, Porter Airlines will fly you from Montreal to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Air Canada - these airlines can fly you to your destination from C$ 206 and C$ 262, respectively. You may be able to fly from Montreal to Chicago for 56% 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: Qantas Airways (97%), Qatar Airways (97%), Avianca (93%).

  • 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$ 1,963, our data indicates the cheapest price to be C$ 235. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 256.

  • 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, September is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 184). Flying from Montreal to Chicago in March is currently the most expensive (average of C$ 359). 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 3 November 2025.
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 3 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 540FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 206AverageC$ 383FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 262AverageC$ 521FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 275AverageC$ 506FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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