Cheap flights from Montreal to Chicago from C$ 176
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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
11 Feb — 18 Feb1
Round-trip
1 adult
Economy
The best prices from Montreal to Chicago are usually found in February or March, booked 67 days in advance, depart on a Thursday or Friday and return on a Thursday
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 6 February 2025.
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 6 February 2025.
Mon 31/39:15 a.m.YUL - ORD
1 stop5h 00mAir Canada
Thu 3/412:59 p.m.ORD - YUL
1 stop4h 22mAir Canada
Deal found 6/2C$ 381
Fri 14/312:48 p.m.YUL - ORD
1 stop8h 56mDelta
Mon 17/31:26 p.m.ORD - YUL
1 stop9h 00mDelta
Deal found 5/2C$ 385
Thu 27/26:50 a.m.YUL - MDW
1 stop6h 20mPorter Airlines
Tue 4/311:15 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 4/2C$ 385
Thu 20/212:49 p.m.YUL - MDW
1 stop6h 22mDelta
Mon 24/26:28 p.m.MDW - YUL
1 stop3h 54mDelta
Deal found 5/2C$ 386
Fri 25/41:35 p.m.YUL - ORD
1 stop8h 42mMultiple Airlines
Sun 27/44:41 p.m.ORD - YUL
1 stop6h 07mMultiple Airlines
Deal found 5/2C$ 395
Thu 20/24:00 p.m.YUL - ORD
1 stop7h 44mAmerican Airlines
Mon 24/25:18 p.m.ORD - YUL
1 stop4h 27mAmerican Airlines
Deal found 5/2C$ 402
Wed 5/36:00 a.m.YUL - ORD
Nonstop2h 57mUnited Airlines
Wed 12/38:00 a.m.ORD - YUL
1 stop5h 17mUnited Airlines
Deal found 5/2C$ 408
Mon 3/38:55 a.m.YUL - MDW
2 stops9h 38mMultiple Airlines
Wed 5/311:15 a.m.MDW - YUL
1 stop4h 30mMultiple Airlines
Deal found 5/2C$ 433
Fri 18/46:00 p.m.YUL - MDW
1 stop24h 59mWestJet
Mon 21/47:00 p.m.MDW - YUL
2 stops28h 39mWestJet
Deal found 5/2C$ 469
Sun 18/56:00 a.m.YUL - ORD
1 stop13h 41mWestJet
Thu 22/57:00 a.m.ORD - YUL
1 stop4h 15mWestJet
Deal found 5/2C$ 471
Thu 27/34:50 p.m.YUL - ORD
1 stop4h 54mKLM
Sun 30/36:45 a.m.ORD - YUL
1 stop4h 13mKLM
Deal found 6/2C$ 478
Thu 20/28:35 a.m.YUL - ORD
1 stop6h 46mFrontier
Mon 24/29:29 a.m.ORD - YUL
2 stops22h 03mFrontier
Deal found 5/2C$ 577
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 6 February 2025.
Mon 31/39:15 a.m.YUL - ORD
1 stop5h 00mAir Canada
Thu 3/412:59 p.m.ORD - YUL
1 stop4h 22mAir Canada
Deal found 6/2C$ 381
Fri 14/312:48 p.m.YUL - ORD
1 stop8h 56mDelta
Mon 17/31:26 p.m.ORD - YUL
1 stop9h 00mDelta
Deal found 5/2C$ 385
Thu 27/26:50 a.m.YUL - MDW
1 stop6h 20mPorter Airlines
Tue 4/311:15 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 4/2C$ 385
Fri 25/41:35 p.m.YUL - ORD
1 stop8h 42mMultiple Airlines
Sun 27/44:41 p.m.ORD - YUL
1 stop6h 07mMultiple Airlines
Deal found 5/2C$ 395
Thu 20/24:00 p.m.YUL - ORD
1 stop7h 44mAmerican Airlines
Mon 24/25:18 p.m.ORD - YUL
1 stop4h 27mAmerican Airlines
Deal found 5/2C$ 402
Sun 6/47:05 a.m.YUL - ORD
1 stop6h 36mWestJet
Sun 13/46:15 p.m.ORD - YUL
1 stop4h 13mWestJet
Deal found 6/2C$ 403
Wed 5/36:00 a.m.YUL - ORD
Nonstop2h 57mUnited Airlines
Wed 12/38:00 a.m.ORD - YUL
1 stop5h 17mUnited Airlines
Deal found 5/2C$ 408
Thu 27/34:50 p.m.YUL - ORD
1 stop4h 54mKLM
Sun 30/36:45 a.m.ORD - YUL
1 stop4h 13mKLM
Deal found 6/2C$ 478
Thu 20/28:35 a.m.YUL - ORD
1 stop6h 46mFrontier
Mon 24/29:29 a.m.ORD - YUL
2 stops22h 03mFrontier
Deal found 5/2C$ 577
Thu 20/212:49 p.m.YUL - MDW
1 stop6h 22mDelta
Mon 24/26:28 p.m.MDW - YUL
1 stop3h 54mDelta
Deal found 5/2C$ 386
Mon 3/38:55 a.m.YUL - MDW
2 stops9h 38mMultiple Airlines
Wed 5/311:15 a.m.MDW - YUL
1 stop4h 30mMultiple Airlines
Deal found 5/2C$ 433
Fri 18/46:00 p.m.YUL - MDW
1 stop24h 59mWestJet
Mon 21/47:00 p.m.MDW - YUL
2 stops28h 39mWestJet
Deal found 5/2C$ 469
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 6 February 2025.
Thu 3/41:10 p.m.YUL - ORD
Nonstop2h 40mAir Canada
Fri 4/46:05 p.m.ORD - YUL
Nonstop2h 24mAir Canada
Deal found 5/2C$ 382
Wed 9/412:30 p.m.YUL - ORD
Nonstop2h 35mBritish Airways
Wed 16/48:25 a.m.ORD - YUL
Nonstop2h 20mBritish Airways
Deal found 6/2C$ 395
Sat 5/412:30 p.m.YUL - ORD
Nonstop2h 35mAmerican Airlines
Mon 7/48:25 a.m.ORD - YUL
Nonstop2h 20mAmerican Airlines
Deal found 6/2C$ 411
Thu 20/26:00 a.m.YUL - ORD
Nonstop2h 57mMultiple Airlines
Mon 24/25:58 p.m.ORD - YUL
Nonstop2h 19mMultiple Airlines
Deal found 5/2C$ 419
Thu 20/26:00 a.m.YUL - ORD
Nonstop2h 57mUnited Airlines
Mon 24/25:58 p.m.ORD - YUL
Nonstop2h 19mUnited Airlines
Deal found 5/2C$ 496
Thu 27/36:00 a.m.YUL - ORD
Nonstop2h 57mLufthansa
Sun 30/37:00 a.m.ORD - YUL
Nonstop2h 28mLufthansa
Deal found 6/2C$ 765
Last-minute flights from Montreal to Chicago
Discover last-minute flight deals from Montreal to Chicago. Data last updated 6 February 2025 and is based on user searches.
Tue 11/26:00 a.m.YUL - MDW
1 stop7h 42mWestJet
Wed 12/21:26 p.m.MDW - YUL
1 stop9h 14mWestJet
Deal found 5/2C$ 684
Wed 12/28:55 a.m.YUL - MDW
1 stop4h 15mPorter Airlines
Sat 15/21:05 p.m.MDW - YUL
1 stop4h 10mPorter Airlines
Deal found 5/2C$ 501
Wed 12/21:30 p.m.YUL - ORD
2 stops23h 00mWestJet
Sat 15/211:15 a.m.ORD - YUL
1 stop11h 37mWestJet
Deal found 5/2C$ 670
Thu 13/26:00 a.m.YUL - ORD
1 stop8h 44mDelta
Sun 16/21:40 p.m.ORD - YUL
1 stop8h 42mDelta
Deal found 5/2C$ 561
Sat 15/29:15 a.m.YUL - ORD
Nonstop2h 39mAir Canada
Tue 18/25:58 p.m.ORD - YUL
Nonstop2h 19mAir Canada
Deal found 4/2C$ 441
Sat 15/27:00 a.m.YUL - MDW
1 stop8h 53mDelta
Tue 18/22:08 p.m.MDW - YUL
1 stop8h 14mDelta
Deal found 4/2C$ 468
Sat 15/23:55 p.m.YUL - ORD
1 stop9h 03mMultiple Airlines
Tue 18/27:13 p.m.ORD - YUL
2 stops18h 42mMultiple Airlines
Deal found 4/2C$ 469
Thu 20/212:49 p.m.YUL - MDW
1 stop6h 22mDelta
Mon 24/26:28 p.m.MDW - YUL
1 stop3h 54mDelta
Deal found 5/2C$ 386
Thu 20/24:00 p.m.YUL - ORD
1 stop7h 44mAmerican Airlines
Mon 24/25:18 p.m.ORD - YUL
1 stop4h 27mAmerican Airlines
Deal found 5/2C$ 402
Thu 20/28:35 a.m.YUL - ORD
1 stop6h 46mFrontier
Mon 24/29:29 a.m.ORD - YUL
2 stops22h 03mFrontier
Deal found 5/2C$ 577
Thu 27/26:50 a.m.YUL - MDW
1 stop6h 20mPorter Airlines
Tue 4/311:15 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 4/2C$ 385
Wed 5/36:00 a.m.YUL - ORD
Nonstop2h 57mUnited Airlines
Wed 12/38:00 a.m.ORD - YUL
1 stop5h 17mUnited Airlines
Deal found 5/2C$ 408
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 6 February 2025.
Sat 8/36:50 a.m.YUL - MDW
1 stop6h 10mPorter Airlines
Deal found 5/2C$ 176
Sun 20/46:15 a.m.YUL - ORD
Nonstop2h 47mAir Canada
Deal found 5/2C$ 187
Tue 25/33:55 p.m.YUL - ORD
2 stops17h 49mMultiple Airlines
Deal found 5/2C$ 202
Wed 2/45:23 p.m.YUL - ORD
1 stop6h 20mDelta
Deal found 4/2C$ 217
Tue 4/36:20 p.m.YUL - ORD
Nonstop2h 35mUnited Airlines
Deal found 5/2C$ 220
Mon 24/22:20 p.m.YUL - ORD
1 stop6h 05mAmerican Airlines
Deal found 5/2C$ 290
Mon 24/28:55 a.m.YUL - MDW
2 stops9h 38mMultiple Airlines
Deal found 5/2C$ 295
Tue 25/36:45 a.m.YUL - MDW
2 stops27h 24mWestJet
Deal found 5/2C$ 298
Fri 28/36:45 a.m.YUL - ORD
2 stops10h 30mWestJet
Deal found 5/2C$ 345
Sun 9/26:00 a.m.YUL - MDW
1 stop5h 32mDelta
Deal found 5/2C$ 438
Find flights from Montreal to Chicago within your budget
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 6 February 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Mon 31/3
9:15 a.m.-1:15 p.m.
1 stop5h 00m
Chicago O'Hare Intl
Thu 3/4
12:59 p.m.-6:21 p.m.
1 stop4h 22m
C$ 381
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Fri 14/3
12:48 p.m.-8:44 p.m.
1 stop8h 56m
Chicago O'Hare Intl
Mon 17/3
1:26 p.m.-11:26 p.m.
1 stop9h 00m
C$ 385
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Thu 27/2
6:50 a.m.-12:10 p.m.
1 stop6h 20m
Chicago Midway
Tue 4/3
11:15 a.m.-4:45 p.m.
1 stop4h 30m
C$ 385
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Thu 20/2
12:49 p.m.-6:11 p.m.
1 stop6h 22m
Chicago Midway
Mon 24/2
6:28 p.m.-11:22 p.m.
1 stop3h 54m
C$ 386
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Fri 25/4
1:35 p.m.-9:17 p.m.
1 stop8h 42m
Chicago O'Hare Intl
Sun 27/4
4:41 p.m.-11:48 p.m.
1 stop6h 07m
C$ 395
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Thu 20/2
4:00 p.m.-10:44 p.m.
1 stop7h 44m
Chicago O'Hare Intl
Mon 24/2
5:18 p.m.-10:45 p.m.
1 stop4h 27m
C$ 402
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Wed 5/3
6:00 a.m.-7:57 a.m.
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/3
8:00 a.m.-2:17 p.m.
1 stop5h 17m
C$ 408
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Mon 3/3
8:55 a.m.-5:33 p.m.
2 stops9h 38m
Chicago Midway
Wed 5/3
11:15 a.m.-4:45 p.m.
1 stop4h 30m
C$ 433
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Fri 18/4
6:00 p.m.-5:59 p.m.
1 stop24h 59m
Chicago Midway
Mon 21/4
7:00 p.m.-12:39 a.m.
2 stops28h 39m
C$ 469
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Sun 18/5
6:00 a.m.-6:41 p.m.
1 stop13h 41m
Chicago O'Hare Intl
Thu 22/5
7:00 a.m.-12:15 p.m.
1 stop4h 15m
C$ 471
Flights are sorted by cheapest round-trip flights first.
Deals found on 5/2
Showing 1-10 of 22 results
1
2
3
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.
Travel insights for flights from Montreal to Chicago
Get recent, data-driven insights about flights from Montreal to Chicago including ideal travel times, pricing trends, and more.
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 January 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, January is the cheapest month in which you can book a flight from Montreal to Chicago (average of C$ 261). Flying from Montreal to Chicago in March is currently the most expensive (average of C$ 355). 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 6 February 2025.
It’s optimal to fly from Montreal to Chicago in the evening. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the morning.
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 Tuesday evenings when fares are most often at their lowest. Monday at noon 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 6 February 2025.
The most flights from YMQ to CHI are scheduled on a Wednesday (17 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (13 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
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 6 February 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and KLM from Montreal to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.