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Cheap flights from Montreal to Chicago from C$ 225

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
30 Mar — 6 Apr1
1 adult

Cheapflights Tip: The best prices from Montreal to Chicago are usually found in February or September, booked 49 days in advance, depart on a Thursday or Friday and return on a Sunday

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 25 March 2025.

Round-trip from

C$ 338

One-way from

C$ 225

Popular in

November

Cheapest in

February

Average price

C$ 474

Good round-trip deal

C$ 541 or less

Good one-way deal

C$ 318 or less
Air Canada
  • Air Canada
  • 19/4-20/4
  • 2 total stops
  • 12h 00m total
  • Montreal to Chicago
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Air Canada
  • Air Canada
  • 11/6
  • 1 total stop
  • 4h 41m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
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Average for round-trip flights in March 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 25 March 2025.

Sat 19/43:15 p.m.YUL - ORD
1 stop5h 15mAir Canada
Sun 20/41:56 p.m.ORD - YUL
1 stop6h 45mAir Canada
Deal found 24/3C$ 338
Tue 6/510:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Mon 12/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 23/3C$ 342
Fri 2/51:15 p.m.YUL - ORD
Nonstop2h 40mUnited Airlines
Tue 6/58:40 a.m.ORD - YUL
Nonstop2h 15mUnited Airlines
Deal found 25/3C$ 351
Wed 25/69:45 a.m.YUL - ORD
Nonstop2h 39mMultiple Airlines
Fri 27/610:40 a.m.ORD - YUL
Nonstop2h 19mMultiple Airlines
Deal found 24/3C$ 355
Tue 29/47:10 a.m.YUL - MDW
1 stop6h 25mDelta
Sat 3/51:16 p.m.MDW - YUL
1 stop9h 12mDelta
Deal found 23/3C$ 361
Fri 25/412:55 p.m.YUL - ORD
1 stop10h 52mAmerican Airlines
Fri 2/58:30 p.m.ORD - YUL
1 stop12h 20mAmerican Airlines
Deal found 25/3C$ 387
Fri 25/47:10 a.m.YUL - ORD
1 stop6h 29mDelta
Tue 29/46:15 p.m.ORD - YUL
1 stop4h 13mDelta
Deal found 24/3C$ 393
Thu 22/51:10 p.m.YUL - MDW
1 stop4h 14mMultiple Airlines
Mon 26/59:40 a.m.MDW - YUL
1 stop6h 40mMultiple Airlines
Deal found 23/3C$ 420
Mon 5/56:00 p.m.YUL - MDW
1 stop16h 07mWestJet
Sat 30/86:45 p.m.MDW - YUL
1 stop27h 33mWestJet
Deal found 23/3C$ 450
Fri 5/96:15 p.m.YUL - ORD
1 stop16h 47mWestJet
Mon 8/97:00 p.m.ORD - YUL
1 stop25h 30mWestJet
Deal found 25/3C$ 457

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 25 March 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

Sat 19/4

3:15 p.m.-7:30 p.m.

1 stop5h 15m

Chicago O'Hare Intl

Sun 20/4

1:56 p.m.-9:41 p.m.

1 stop6h 45m

C$ 338

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 6/5

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Sun 11/5

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 342

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/5

6:40 p.m.-8:12 p.m.

Nonstop2h 32m

Chicago O'Hare Intl

Tue 6/5

8:40 a.m.-11:55 a.m.

Nonstop2h 15m

C$ 351

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 25/6

9:45 a.m.-11:24 a.m.

Nonstop2h 39m

Chicago O'Hare Intl

Fri 27/6

10:40 a.m.-1:59 p.m.

Nonstop2h 19m

C$ 355

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 29/4

7:10 a.m.-12:35 p.m.

1 stop6h 25m

Chicago Midway

Sat 3/5

1:16 p.m.-11:28 p.m.

1 stop9h 12m

C$ 361

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/5

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

Nonstop2h 35m

Chicago O'Hare Intl

Tue 6/5

8:15 p.m.-9:50 a.m.

1 stop12h 35m

C$ 364

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 21/4

6:00 p.m.-11:59 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Mon 28/4

5:30 a.m.-4:42 p.m.

1 stop10h 12m

C$ 413

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/5

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 26/5

9:40 a.m.-5:20 p.m.

1 stop6h 40m

C$ 420

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 5/5

6:00 p.m.-9:07 a.m.

1 stop16h 07m

Chicago Midway

Sat 30/8

6:45 p.m.-11:18 p.m.

1 stop27h 33m

C$ 450

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 5/9

12:45 p.m.-2:20 p.m.

1 stop26h 35m

Chicago O'Hare Intl

Mon 8/9

7:35 p.m.-11:09 p.m.

1 stop26h 34m

C$ 457

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/3

Showing 1-10 of 23 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 21 March 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 25 March 2025.

It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight in the evening.

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.

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 25 March 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and Aeromexico 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
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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
7,890 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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
Aeromexico
7.5
Good
1,700 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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
8,605 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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
7,890 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

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$ 338, Air Canada will fly you from Montreal to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Porter Airlines and United Airlines - these airlines can fly you to your destination from C$ 342 and C$ 351, respectively. You may be able to fly from Montreal to Chicago for 32% 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$ 225 on Air Canada. Other airlines that offer cheap prices include Porter Airlines from C$ 225 and Lufthansa from C$ 226 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: Emirates (100%), ANA (89%), Avianca (87%).

  • 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$ 2,646, our data indicates the cheapest price to be C$ 229. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 332.

  • 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 25 March 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 25 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 343AverageC$ 471FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 361AverageC$ 501FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 369AverageC$ 591FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 371AverageC$ 493FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 394AverageC$ 520FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 457AverageC$ 620FlexibilityNo 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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