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Cheap flights from Montreal to Chicago from C$ 194

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
2 Jun — 9 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Montreal to Chicago are usually found in March or September, booked 67 days in advance, depart on a Thursday or Saturday 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 3 May 2026.

Thu 4/66:30 a.m.
YUL
-
MDW
1 stop4h 05m
Porter Airlines
Sun 7/610:15 a.m.
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 29/4C$ 281
Thu 28/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 31/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 29/4C$ 311
Fri 12/66:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 14/610:15 a.m.
MDW
-
YUL
1 stop7h 00m
Porter Airlines
Deal found 30/4C$ 315
Thu 21/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 24/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 30/4C$ 318
Fri 22/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Sun 24/510:30 a.m.
MDW
-
YUL
1 stop8h 40m
Porter Airlines
Deal found 29/4C$ 321
Thu 4/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Mon 8/610:15 a.m.
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 2/5C$ 328
Fri 29/56:30 a.m.
YUL
-
MDW
1 stop9h 05m
Porter Airlines
Mon 1/63:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 28/4C$ 342
Tue 14/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Thu 23/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 28/4C$ 347
Fri 29/56:30 p.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 31/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 28/4C$ 364
Tue 16/64:30 p.m.
YUL
-
ORD
1 stop4h 46m
Air Canada
Tue 23/67:25 a.m.
ORD
-
YUL
1 stop5h 22m
Air Canada
Deal found 2/5C$ 374
Thu 4/62:30 p.m.
YUL
-
ORD
1 stop6h 46m
Air Canada
Sun 7/67:25 a.m.
ORD
-
YUL
1 stop5h 20m
Air Canada
Deal found 29/4C$ 378
Mon 15/61:15 p.m.
YUL
-
ORD
Nonstop2h 35m
Air Canada
Tue 23/68:35 a.m.
ORD
-
YUL
Nonstop2h 23m
Air Canada
Deal found 28/4C$ 379

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 3 May 2026.

Round-trip from

C$ 281

One-way from

C$ 194

Popular in

December

Cheapest in

March

Average price

C$ 453

Good round-trip deal

C$ 570 or less

Good one-way deal

C$ 367 or less
Porter Airlines
  • Porter Airlines
  • 4/6-7/6
  • 2 total stops
  • 10h 05m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/5
  • 1 total stop
  • 9h 05m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 3 May 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 - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

12:49 p.m.-8:14 p.m.

1 stop8h 25m

Chicago O'Hare Intl

Sat 30/5

1:44 p.m.-11:13 p.m.

1 stop8h 29m

C$ 413

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 27/5

7:00 a.m.-1:47 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Thu 28/5

2:59 p.m.-11:57 p.m.

1 stop7h 58m

C$ 416

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

12:40 p.m.-6:41 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Fri 12/6

2:07 p.m.-11:28 p.m.

1 stop8h 21m

C$ 417

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

12:40 p.m.-9:09 p.m.

1 stop9h 29m

Chicago Midway

Fri 12/6

5:11 p.m.-11:55 p.m.

1 stop5h 44m

C$ 417

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 18/6

6:00 a.m.-9:14 a.m.

1 stop4h 14m

Chicago Midway

Sat 20/6

9:17 a.m.-4:20 p.m.

1 stop6h 03m

C$ 417

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 1/6

7:10 a.m.-11:47 a.m.

1 stop5h 37m

Chicago O'Hare Intl

Fri 5/6

2:59 p.m.-11:57 p.m.

1 stop7h 58m

C$ 419

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 12/5

12:49 p.m.-6:33 p.m.

1 stop6h 44m

Chicago Midway

Fri 15/5

12:53 p.m.-11:57 p.m.

1 stop10h 04m

C$ 419
Quickest round-trip

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

8:40 a.m.-10:18 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

Fri 12/6

8:20 p.m.-1:51 a.m.

1 stop4h 31m

C$ 421

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 30/5

6:00 a.m.-12:42 p.m.

1 stop7h 42m

Chicago Midway

Mon 1/6

6:23 a.m.-5:43 p.m.

1 stop10h 20m

C$ 424

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 1/6

7:00 a.m.-4:12 p.m.

1 stop10h 12m

Chicago Midway

Tue 2/6

5:15 p.m.-11:57 p.m.

1 stop5h 42m

C$ 424

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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

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 66 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, February is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 69). Flying from Montreal to Chicago in January is currently the most expensive (average of C$ 182). 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 May 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 3 May 2026.

The most flights from YMQ to CHI are scheduled on a Friday (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 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 May 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
435 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,681 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,671 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,990 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 Air Canada fly from Montreal to Chicago in about 2h 38m. The time it takes to get you to your destination can typically vary by up to 5h 47m. 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$ 175, 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 Air Canada - these airlines can fly you to your destination from C$ 178 and C$ 246, respectively. You may be able to fly from Montreal to Chicago for 58% 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 (100%), Japan Airlines (95%), ANA (88%).

  • 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$ 789, our data indicates the cheapest price to be C$ 252. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 381.

  • 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$ 69). Flying from Montreal to Chicago in January is currently the most expensive (average of C$ 182). 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 May 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 3 May 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 175AverageC$ 359FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 178AverageC$ 437FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 246AverageC$ 509FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 254AverageC$ 487FlexibilityNo 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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