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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
1 adult

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.

Round-trip from

C$ 381

One-way from

C$ 176

Popular in

November

Cheapest in

February

Average price

C$ 412

Good round-trip deal

C$ 493 or less

Good one-way deal

C$ 270 or less
Air Canada
  • Air Canada
  • 31/3-3/4
  • 2 total stops
  • 9h 22m total
  • Montreal to Chicago
Porter Airlines
  • Porter Airlines
  • 8/3
  • 1 total stop
  • 6h 10m total
  • Montreal to Chicago
Highest demand for flights based on searches. 5% potential increase in price (C$ 38 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
Average for round-trip flights in February 2025
Price to beat on a round-trip flight from Montreal (YMQ) to Chicago (CHI).
Price to beat on a one-way flight from Montreal (YMQ) to Chicago (CHI).

Find flight deals from Montreal to Chicago

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 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

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
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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.

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.

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

8.0
Very good

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews