Cheap flights from Montreal to Chicago from C$ 202
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 14/7. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Montreal to Chicago are usually found in March or May, booked 45 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 12 junio 2025.
Find flight deals from Montreal to Chicago
Cheapest flights from Montreal to ChicagoExplore 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 12 junio 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 12 junio 2025.
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 12 junio 2025.
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
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
vie. 11/7
1:10 p.m.-4:24 p.m.
1 stop4h 14m
Chicago Midway
dom. 13/7
9:40 a.m.-4:00 p.m.
1 stop5h 20m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
mié. 27/8
1:20 p.m.-2:55 p.m.
Nonstop2h 35m
Chicago O'Hare Intl
mié. 3/9
8:40 a.m.-11:57 a.m.
Nonstop2h 17m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
sáb. 30/8
7:50 a.m.-10:49 p.m.
1 stop15h 59m
Chicago O'Hare Intl
mar. 2/9
9:11 p.m.-12:28 p.m.
1 stop14h 17m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
vie. 3/10
7:00 a.m.-4:38 p.m.
1 stop10h 38m
Chicago O'Hare Intl
mié. 8/10
10:35 a.m.-4:00 p.m.
1 stop4h 25m
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
vie. 3/10
7:00 a.m.-4:23 p.m.
1 stop10h 23m
Chicago Midway
mié. 8/10
9:30 a.m.-4:00 p.m.
1 stop5h 30m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
jue. 17/7
6:15 a.m.-7:59 a.m.
Nonstop2h 44m
Chicago O'Hare Intl
lun. 21/7
8:40 a.m.-11:58 a.m.
Nonstop2h 18m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
jue. 17/7
6:15 a.m.-7:59 a.m.
Nonstop2h 44m
Chicago O'Hare Intl
mar. 22/7
2:07 p.m.-5:26 p.m.
Nonstop2h 19m
MontrealChicago
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
sáb. 11/10
7:00 a.m.-9:44 p.m.
1 stop15h 44m
Chicago Midway
mié. 15/10
9:15 a.m.-6:45 p.m.
1 stop8h 30m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
jue. 24/7
6:15 a.m.-7:59 a.m.
Nonstop2h 44m
Chicago O'Hare Intl
lun. 28/7
7:15 a.m.-10:40 a.m.
Nonstop2h 25m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
sáb. 30/8
6:45 a.m.-7:19 p.m.
2 stops13h 34m
Chicago O'Hare Intl
mar. 2/9
6:10 a.m.-11:16 p.m.
1 stop16h 06m
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.
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 9 June 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 45 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$ 352). 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 12 junio 2025.
It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 9% 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 Sunday evenings when fares are most often at their lowest. Sunday 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 12 junio 2025.
The most flights from YMQ to CHI are scheduled on a Monday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 12 junio 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and United Airlines 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.
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mary,Jun 2025
FLL - YYZ
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.
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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 12 junio 2025.
Top 5 airlines flying from Montreal to Chicago
Discover the top 5 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 12 junio 2025.
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!