Cheap flights from Montreal to Chicago from C$ 226
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 31/12. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
17 Jan — 24 Jan1
Round-trip
1 adult
Economy
Round-trip
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 Monday
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 18 December 2025.
Wed 31/125:25 p.m.YUL - ORD
1 stop17h 19mUnited Airlines
Mon 5/17:00 a.m.ORD - YUL
1 stop4h 46mUnited Airlines
Deal found 16/12C$ 415
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 16/12C$ 416
Wed 31/128:50 a.m.YUL - ORD
2 stops7h 20mAir Canada
Sat 3/18:40 p.m.ORD - YUL
1 stop4h 13mAir Canada
Deal found 16/12C$ 460
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 16/12C$ 460
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 2/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 15/12C$ 475
Wed 31/128:50 a.m.YUL - ORD
2 stops7h 20mAir Canada
Mon 5/18:45 p.m.ORD - YUL
1 stop4h 08mAir Canada
Deal found 16/12C$ 503
Wed 24/126:25 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Wed 31/123:55 p.m.ORD - YUL
1 stop6h 27mAir Canada
Deal found 17/12C$ 530
Fri 26/1212:10 p.m.YUL - ORD
1 stop6h 38mAir Canada
Wed 31/123:55 p.m.ORD - YUL
1 stop6h 27mAir Canada
Deal found 16/12C$ 544
Sat 27/126:00 a.m.YUL - ORD
Nonstop3h 05mAir Canada
Mon 23/210:35 a.m.ORD - YUL
Nonstop2h 25mAir Canada
Deal found 16/12C$ 552
Wed 31/128:50 a.m.YUL - ORD
2 stops7h 20mAir Canada
Sun 4/110:35 a.m.ORD - YUL
Nonstop2h 25mAir Canada
Deal found 16/12C$ 566
Fri 26/1210:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Wed 31/1211:00 a.m.MDW - YUL
1 stop5h 15mPorter Airlines
Deal found 16/12C$ 572
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 17/12C$ 592
Best flights from Montreal to Chicago
Discover carefully curated flight deals from Montreal to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 18 December 2025.
Sun 15/26:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Sun 15/26:00 p.m.ORD - YUL
Nonstop2h 17mUnited Airlines
Deal found 17/12C$ 260
Wed 4/27:00 a.m.YUL - ORD
1 stop7h 22mAmerican Airlines
Sat 7/26:38 a.m.ORD - YUL
1 stop7h 42mAmerican Airlines
Deal found 17/12C$ 260
Thu 19/26:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 17/12C$ 270
Sat 14/212:52 p.m.YUL - ORD
1 stop8h 52mDelta
Tue 17/26:15 a.m.ORD - YUL
1 stop6h 25mDelta
Deal found 15/12C$ 298
Fri 6/26:45 a.m.YUL - MDW
1 stop4h 25mMultiple Airlines
Mon 9/27:00 p.m.MDW - YUL
2 stops24h 14mMultiple Airlines
Deal found 17/12C$ 376
Fri 13/26:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Wed 18/210:35 a.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 260
Sun 15/26:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 15/24:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 17/12C$ 271
Fri 6/26:00 a.m.YUL - ORD
Nonstop3h 05mUnited Airlines
Mon 9/23:35 p.m.ORD - YUL
1 stop5h 07mUnited Airlines
Deal found 17/12C$ 270
Thu 5/26:00 a.m.YUL - ORD
1 stop8h 13mDelta
Sun 8/25:35 p.m.ORD - YUL
1 stop4h 51mDelta
Deal found 16/12C$ 298
Fri 13/26:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 13/24:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 17/12C$ 271
Sat 14/27:00 a.m.YUL - MDW
1 stop9h 21mDelta
Tue 17/212:46 p.m.MDW - YUL
1 stop10h 13mDelta
Deal found 15/12C$ 298
Mon 2/24:45 p.m.YUL - ORD
Nonstop3h 06mUnited Airlines
Sat 7/21:00 p.m.ORD - YUL
1 stop5h 48mUnited Airlines
Deal found 17/12C$ 271
Wed 4/24:45 p.m.YUL - ORD
Nonstop3h 06mUnited Airlines
Sat 7/26:05 a.m.ORD - YUL
1 stop6h 23mUnited Airlines
Deal found 17/12C$ 271
Fri 10/410:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Mon 13/411:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 16/12C$ 303
Tue 10/212:54 p.m.YUL - MDW
1 stop6h 01mDelta
Thu 19/29:34 a.m.MDW - YUL
1 stop5h 21mDelta
Deal found 17/12C$ 309
Thu 19/23:00 p.m.YUL - ORD
1 stop7h 34mUnited Airlines
Mon 23/21:02 p.m.ORD - YUL
1 stop5h 46mUnited Airlines
Deal found 17/12C$ 278
Thu 9/46:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 16/411:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 17/12C$ 327
Sat 31/14:45 p.m.YUL - ORD
Nonstop3h 06mUnited Airlines
Sat 7/25:52 p.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 300
Fri 6/26:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 9/211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 17/12C$ 371
Wed 8/46:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 12/411:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 17/12C$ 376
Wed 8/411:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Tue 14/411:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 17/12C$ 376
Direct flights from Montreal to Chicago
Explore direct flight options from Montreal to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 18 December 2025.
Thu 12/26:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Mon 16/26:00 p.m.ORD - YUL
Nonstop2h 17mUnited Airlines
Deal found 17/12C$ 260
Thu 5/26:00 a.m.YUL - ORD
Nonstop3h 05mUnited Airlines
Sun 8/25:52 p.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 262
Fri 6/23:50 p.m.YUL - ORD
Nonstop3h 00mAmerican Airlines
Mon 9/211:50 a.m.ORD - YUL
Nonstop2h 18mAmerican Airlines
Deal found 17/12C$ 266
Tue 10/26:25 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Thu 19/27:15 a.m.ORD - YUL
Nonstop2h 05mAir Canada
Deal found 17/12C$ 271
Sat 31/14:45 p.m.YUL - ORD
Nonstop3h 06mUnited Airlines
Sat 7/25:52 p.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 300
Sat 31/16:25 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Sat 7/212:50 p.m.ORD - YUL
Nonstop2h 11mAir Canada
Deal found 17/12C$ 307
Mon 2/24:45 p.m.YUL - ORD
Nonstop3h 06mAir Canada
Sat 7/212:50 p.m.ORD - YUL
Nonstop2h 11mAir Canada
Deal found 17/12C$ 309
Thu 19/26:25 p.m.YUL - ORD
Nonstop2h 45mUnited Airlines
Mon 23/210:35 a.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 324
Fri 30/16:00 a.m.YUL - ORD
Nonstop3h 05mUnited Airlines
Mon 2/210:35 a.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 16/12C$ 338
Thu 5/23:50 p.m.YUL - ORD
Nonstop3h 00mAmerican Airlines
Sun 8/211:50 a.m.ORD - YUL
Nonstop2h 18mAmerican Airlines
Deal found 16/12C$ 340
Last-minute flights from Montreal to Chicago
Discover last-minute flight deals from Montreal to Chicago. Data last updated 18 December 2025 and is based on user searches.
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 16/12C$ 416
Thu 15/13:50 p.m.YUL - ORD
Nonstop3h 00mAmerican Airlines
Wed 4/28:09 a.m.ORD - YUL
1 stop6h 11mAmerican Airlines
Deal found 16/12C$ 346
Sun 18/110:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Thu 29/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 17/12C$ 378
Fri 23/11:02 p.m.YUL - MDW
1 stop5h 53mDelta
Mon 26/11:26 p.m.MDW - YUL
1 stop8h 46mDelta
Deal found 16/12C$ 422
Fri 30/13:50 p.m.YUL - ORD
Nonstop3h 00mAmerican Airlines
Fri 6/28:56 p.m.ORD - YUL
1 stop17h 24mAmerican Airlines
Deal found 16/12C$ 325
Fri 30/16:00 a.m.YUL - ORD
Nonstop3h 05mUnited Airlines
Mon 2/21:00 p.m.ORD - YUL
1 stop7h 42mUnited Airlines
Deal found 16/12C$ 338
Fri 30/17:00 a.m.YUL - ORD
1 stop6h 05mUnited Airlines
Fri 6/26:05 a.m.ORD - YUL
1 stop6h 23mUnited Airlines
Deal found 16/12C$ 344
Fri 30/16:00 a.m.YUL - MDW
1 stop7h 46mMultiple Airlines
Fri 6/211:05 a.m.MDW - YUL
1 stop4h 25mMultiple Airlines
Deal found 16/12C$ 366
Fri 30/16:00 a.m.YUL - MDW
1 stop7h 46mMultiple Airlines
Mon 2/211:05 a.m.MDW - YUL
1 stop4h 25mMultiple Airlines
Deal found 16/12C$ 387
Sat 31/14:45 p.m.YUL - ORD
Nonstop3h 06mUnited Airlines
Sat 7/25:52 p.m.ORD - YUL
Nonstop2h 25mUnited Airlines
Deal found 17/12C$ 300
Sat 31/16:25 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Sat 7/212:50 p.m.ORD - YUL
Nonstop2h 11mAir Canada
Deal found 17/12C$ 307
Sat 31/16:00 a.m.YUL - MDW
1 stop7h 46mDelta
Sat 7/21:26 p.m.MDW - YUL
1 stop8h 46mDelta
Deal found 17/12C$ 371
One-way flights from Montreal to Chicago
Search for one-way flight options from Montreal to Chicago. Find affordable one-way fares based on user searches. Data last updated 18 December 2025.
Wed 31/128:50 a.m.YUL - ORD
2 stops7h 20mAir Canada
Deal found 16/12C$ 226
Tue 17/36:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Deal found 17/12C$ 229
Mon 12/110:45 a.m.YUL - ORD
3 stops25h 37mMultiple Airlines
Deal found 17/12C$ 233
Tue 17/26:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Deal found 16/12C$ 233
Sun 8/36:00 a.m.YUL - ORD
Nonstop3h 00mUnited Airlines
Deal found 17/12C$ 234
Thu 15/16:45 a.m.YUL - ORD
1 stop15h 12mMultiple Airlines
Deal found 16/12C$ 238
Mon 9/39:25 a.m.YUL - ORD
Nonstop2h 53mAir Canada
Deal found 15/12C$ 240
Mon 16/38:00 a.m.YUL - ORD
1 stop28h 26mMultiple Airlines
Deal found 16/12C$ 242
Mon 12/16:25 p.m.YUL - ORD
Nonstop2h 45mAir Canada
Deal found 16/12C$ 244
Sun 10/510:40 a.m.YUL - MDW
1 stop6h 44mPorter Airlines
Deal found 16/12C$ 244
Tue 13/18:00 a.m.YUL - ORD
1 stop6h 01mAir Canada
Deal found 16/12C$ 245
Wed 31/125:25 p.m.YUL - ORD
1 stop17h 19mUnited Airlines
Deal found 16/12C$ 249
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 18 December 2025.
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 18 December 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
Sun 15/2
6:00 a.m.-8:00 a.m.
Nonstop3h 00m
Chicago O'Hare Intl
Sun 15/2
6:00 p.m.-9:17 p.m.
Nonstop2h 17m
C$ 260
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Wed 4/2
7:00 a.m.-1:22 p.m.
1 stop7h 22m
Chicago O'Hare Intl
Sat 7/2
6:38 a.m.-3:20 p.m.
1 stop7h 42m
C$ 260
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Fri 13/2
6:00 a.m.-8:00 a.m.
Nonstop3h 00m
Chicago O'Hare Intl
Wed 18/2
10:35 a.m.-2:00 p.m.
Nonstop2h 25m
C$ 260
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Thu 19/2
6:45 a.m.-10:05 a.m.
1 stop4h 20m
Chicago Midway
Mon 23/2
11:00 a.m.-5:45 p.m.
1 stop5h 45m
C$ 270
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Fri 6/2
6:00 a.m.-8:05 a.m.
Nonstop3h 05m
Chicago O'Hare Intl
Mon 9/2
3:35 p.m.-9:42 p.m.
1 stop5h 07m
C$ 270
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Sun 15/2
6:45 a.m.-10:05 a.m.
1 stop4h 20m
Chicago Midway
Sun 15/2
4:15 p.m.-10:45 p.m.
1 stop5h 30m
C$ 271
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Fri 13/2
6:45 a.m.-10:05 a.m.
1 stop4h 20m
Chicago Midway
Fri 13/2
4:15 p.m.-10:45 p.m.
1 stop5h 30m
C$ 271
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Mon 2/2
4:45 p.m.-6:51 p.m.
Nonstop3h 06m
Chicago O'Hare Intl
Sat 7/2
1:00 p.m.-7:48 p.m.
1 stop5h 48m
C$ 271
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Wed 4/2
4:45 p.m.-6:51 p.m.
Nonstop3h 06m
Chicago O'Hare Intl
Sat 7/2
6:05 a.m.-1:28 p.m.
1 stop6h 23m
C$ 271
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Thu 19/2
3:00 p.m.-9:34 p.m.
1 stop7h 34m
Chicago O'Hare Intl
Mon 23/2
1:02 p.m.-7:48 p.m.
1 stop5h 46m
C$ 278
Flights are sorted by cheapest round-trip flights first.
Deals found on 16/12
Showing 1-10 of 43 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 12 December 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$ 180). Flying from Montreal to Chicago in December is currently the most expensive (average of C$ 373). 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 18 December 2025.
It’s optimal to fly from Montreal to Chicago in the evening. By choosing this option you can save up to 53% 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 18 December 2025.
The most flights from YMQ to CHI are scheduled on a Tuesday (20 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 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 92% 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$ 403.
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 Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 4h 22m.
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 Detroit (DTW) offer the fastest connection on this route, with an average layover time of 1h 06m.
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 18 December 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.
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 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 United Airlines, American Airlines, and Porter Airlines fly from Montreal to Chicago in about 3h. The time it takes to get you to your destination can typically vary by up to 4h 22m. 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$ 177, 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$ 196 and C$ 255, 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: Qatar Airways (88%), ANA (87%), Qantas Airways (80%).
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$ 1,461, our data indicates the cheapest price to be C$ 232. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 242.
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$ 180). Flying from Montreal to Chicago in December is currently the most expensive (average of C$ 373). 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.
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.
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 18 December 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 18 December 2025.
Browse through other flights departing from Montreal. Flights are based on user searches made on Cheapflights and were last updated on 18 December 2025.
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 18 December 2025.
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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