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Cheap flights from Montreal to Chicago from C$ 207

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
25 Feb — 4 Mar1
1 adult

The best prices from Montreal to Chicago are usually found in February or March, booked 49 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 20 February 2025.

Round-trip from

C$ 368

One-way from

C$ 207

Popular in

November

Cheapest in

February

Average price

C$ 423

Good round-trip deal

C$ 503 or less

Good one-way deal

C$ 266 or less
15/3-19/3
  • 15/3-19/3
  • 4 total stops
  • 43h 16m total
  • Montreal to Chicago
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18/3
  • 18/3
  • 2 total stops
  • 17h 34m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Montreal (YMQ) to Chicago (CHI).
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Price to beat on a one-way flight from Montreal (YMQ) to Chicago (CHI).
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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 20 February 2025.

Sat 15/33:30 p.m.YUL - ORD
1 stop9h 26mMultiple Airlines
Wed 19/35:55 a.m.ORD - YUL
3 stops33h 50mMultiple Airlines
Deal found 19/2C$ 368
Sun 6/46:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Sun 13/411:15 a.m.MDW - YUL
1 stop4h 37mPorter Airlines
Deal found 20/2C$ 368
Fri 21/38:50 a.m.YUL - ORD
1 stop5h 06mAir Canada
Mon 24/38:30 p.m.ORD - YUL
1 stop4h 23mAir Canada
Deal found 19/2C$ 369
Thu 24/49:45 a.m.YUL - ORD
Nonstop2h 47mLufthansa
Sun 27/47:20 a.m.ORD - YUL
Nonstop2h 16mLufthansa
Deal found 19/2C$ 371
Thu 24/48:30 a.m.YUL - ORD
1 stop5h 45mUnited Airlines
Sun 27/47:20 a.m.ORD - YUL
Nonstop2h 16mUnited Airlines
Deal found 19/2C$ 372
Sat 22/312:55 p.m.YUL - ORD
1 stop5h 31mBritish Airways
Sat 29/34:40 p.m.ORD - YUL
1 stop5h 10mBritish Airways
Deal found 20/2C$ 392
Fri 25/412:50 p.m.YUL - MDW
1 stop6h 30mDelta
Tue 29/412:48 p.m.MDW - YUL
1 stop10h 11mDelta
Deal found 20/2C$ 392
Sat 5/412:30 p.m.YUL - ORD
Nonstop2h 35mAmerican Airlines
Mon 7/48:30 p.m.ORD - YUL
1 stop12h 20mAmerican Airlines
Deal found 19/2C$ 415
Fri 13/66:00 a.m.YUL - ORD
1 stop4h 22mDelta
Sun 22/67:00 a.m.ORD - YUL
1 stop8h 02mDelta
Deal found 19/2C$ 426
Thu 10/411:50 a.m.YUL - MDW
1 stop5h 50mMultiple Airlines
Sat 12/412:58 p.m.MDW - YUL
1 stop10h 17mMultiple Airlines
Deal found 19/2C$ 460
Sun 15/67:30 a.m.YUL - MDW
1 stop11h 33mWestJet
Sat 21/66:45 p.m.MDW - YUL
1 stop18h 13mWestJet
Deal found 19/2C$ 487
Fri 21/31:30 p.m.YUL - ORD
2 stops9h 17mWestJet
Mon 24/36:15 p.m.ORD - YUL
1 stop4h 11mWestJet
Deal found 19/2C$ 490

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 20 February 2025.

Fly from

Montreal

Fly to

Chicago

Route

Depart

Return

Price

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 15/3

3:30 p.m.-11:56 p.m.

1 stop9h 26m

Chicago O'Hare Intl

Wed 19/3

5:55 a.m.-4:45 p.m.

3 stops33h 50m

C$ 368

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 6/4

6:50 a.m.-10:20 a.m.

1 stop4h 30m

Chicago Midway

Sun 13/4

11:15 a.m.-4:52 p.m.

1 stop4h 37m

C$ 368

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 21/3

6:00 a.m.-7:57 a.m.

Nonstop2h 57m

Chicago O'Hare Intl

Mon 24/3

8:30 p.m.-1:53 a.m.

1 stop4h 23m

C$ 369

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 24/4

9:45 a.m.-11:32 a.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sun 27/4

7:20 a.m.-10:36 a.m.

Nonstop2h 16m

C$ 371

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 24/4

8:30 a.m.-1:15 p.m.

1 stop5h 45m

Chicago O'Hare Intl

Sun 27/4

7:20 a.m.-10:36 a.m.

Nonstop2h 16m

C$ 372

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 22/3

12:55 p.m.-5:26 p.m.

1 stop5h 31m

Chicago O'Hare Intl

Sat 29/3

4:40 p.m.-10:50 p.m.

1 stop5h 10m

C$ 392

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 25/4

12:50 p.m.-6:20 p.m.

1 stop6h 30m

Chicago Midway

Tue 29/4

12:48 p.m.-11:59 p.m.

1 stop10h 11m

C$ 392

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 5/4

12:30 p.m.-2:05 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Mon 7/4

8:30 p.m.-9:50 a.m.

1 stop12h 20m

C$ 415

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 13/6

6:00 a.m.-9:22 a.m.

1 stop4h 22m

Chicago O'Hare Intl

Sun 22/6

7:00 a.m.-4:02 p.m.

1 stop8h 02m

C$ 426

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/4

11:50 a.m.-4:40 p.m.

1 stop5h 50m

Chicago Midway

Sat 12/4

12:58 p.m.-12:15 a.m.

1 stop10h 17m

C$ 460

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

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 14 February 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 49 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 20 February 2025.

It’s optimal to fly from Montreal to Chicago in the evening. By choosing this option you can save up to 40% 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 20 February 2025.

The most flights from YMQ to CHI are scheduled on a Wednesday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 20 February 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines 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.
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

Delta
8.0
Very good
8,227 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

United Airlines
7.4
Good
8,771 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

WestJet
7.2
Good
2,799 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.3

Crew

8.5

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

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.

  • What are the cheapest airlines flying from Montreal to Chicago round-trip?

    Currently priced at C$ 368, Porter Airlines will fly you from Montreal to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and Lufthansa - these airlines can fly you to your destination from C$ 369 and C$ 371, respectively. You may be able to fly from Montreal to Chicago for 25% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Montreal to Chicago one-way?

    One-way options have recently been found by users for as low as C$ 210 on Porter Airlines. Other airlines that offer cheap prices include United Airlines from C$ 213 and Air Canada from C$ 217 one-way.

  • 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: ANA (87%), Avianca (86%), Copa Airlines (79%).

  • 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$ 1,765, our data indicates the cheapest price to be C$ 185. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 349.

  • 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, 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.

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 20 February 2025.
Air Canada flights from Montreal to Chicago
Porter Airlines flights from Montreal to Chicago
United Airlines flights from Montreal to Chicago

Top 6 airlines flying from Montreal to Chicago

Discover the top 6 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 20 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 338AverageC$ 468FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 366AverageC$ 489FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 368AverageC$ 514FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 372AverageC$ 589FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 390AverageC$ 515FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 453AverageC$ 613FlexibilityNo cancel feeOn-time60%
Search WestJet 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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