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Cheap flights from Montreal to Chicago from C$ 195

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Montreal to Chicago are usually found in March or May, 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 29 April 2025.

Round-trip from

C$ 320

One-way from

C$ 195

Popular in

November

Cheapest in

March

Average price

C$ 522

Good round-trip deal

C$ 485 or less

Good one-way deal

C$ 315 or less
Porter Airlines
  • Porter Airlines
  • 22/5-26/5
  • 2 total stops
  • 9h 34m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 28/5
  • 1 total stop
  • 4h 44m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 5% potential increase in price (C$ 39 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 April 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 29 April 2025.

Thu 22/51:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 26/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 28/4C$ 320
Fri 23/56:15 a.m.YUL - ORD
Nonstop2h 44mAir Canada
Mon 26/57:19 a.m.ORD - YUL
Nonstop2h 21mAir Canada
Deal found 28/4C$ 348
Thu 22/51:15 p.m.YUL - ORD
Nonstop2h 32mUnited Airlines
Mon 26/55:02 a.m.ORD - YUL
1 stop17h 24mUnited Airlines
Deal found 28/4C$ 382
Sun 25/512:30 p.m.YUL - ORD
Nonstop2h 35mAmerican Airlines
Sun 1/67:00 a.m.ORD - YUL
1 stop7h 25mAmerican Airlines
Deal found 28/4C$ 387
Sun 25/56:00 a.m.YUL - ORD
1 stop7h 41mDelta
Sun 1/61:45 p.m.ORD - YUL
1 stop8h 31mDelta
Deal found 28/4C$ 389
Mon 26/56:15 a.m.YUL - MDW
1 stop8h 00mDelta
Mon 2/61:55 p.m.MDW - YUL
1 stop8h 24mDelta
Deal found 27/4C$ 391
Thu 22/59:45 a.m.YUL - ORD
Nonstop2h 39mMultiple Airlines
Mon 26/58:25 p.m.ORD - YUL
1 stop4h 26mMultiple Airlines
Deal found 28/4C$ 392
Sat 24/57:00 a.m.YUL - MDW
2 stops15h 13mMultiple Airlines
Tue 27/59:40 a.m.MDW - YUL
1 stop5h 20mMultiple Airlines
Deal found 27/4C$ 443
Tue 27/56:00 a.m.YUL - ORD
1 stop7h 41mWestJet
Tue 3/611:07 a.m.ORD - YUL
1 stop5h 33mWestJet
Deal found 27/4C$ 446
Wed 7/512:30 p.m.YUL - ORD
Nonstop2h 35mWestJet Encore
Sun 11/58:24 a.m.ORD - YUL
Nonstop2h 20mWestJet Encore
Deal found 27/4C$ 478
Thu 10/712:46 p.m.YUL - MDW
1 stop9h 55mWestJet
Sat 12/71:46 p.m.MDW - YUL
1 stop8h 29mWestJet
Deal found 27/4C$ 478

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 29 April 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 - 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.-4:00 p.m.

1 stop5h 20m

C$ 320

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 23/5

6:15 a.m.-7:59 a.m.

Nonstop2h 44m

Chicago O'Hare Intl

Mon 26/5

7:19 a.m.-10:40 a.m.

Nonstop2h 21m

C$ 348

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 22/5

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

Nonstop2h 39m

Chicago O'Hare Intl

Mon 26/5

7:19 a.m.-10:40 a.m.

Nonstop2h 21m

C$ 382

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 25/5

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

Nonstop2h 35m

Chicago O'Hare Intl

Sun 1/6

7:00 a.m.-3:25 p.m.

1 stop7h 25m

C$ 387

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 25/5

6:00 a.m.-12:41 p.m.

1 stop7h 41m

Chicago O'Hare Intl

Sun 1/6

1:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 389

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 26/5

6:15 a.m.-1:15 p.m.

1 stop8h 00m

Chicago Midway

Mon 2/6

1:55 p.m.-11:19 p.m.

1 stop8h 24m

C$ 391

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 22/5

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

Nonstop2h 39m

Chicago O'Hare Intl

Mon 26/5

8:25 p.m.-1:51 a.m.

1 stop4h 26m

C$ 392

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 24/5

7:00 a.m.-9:13 p.m.

2 stops15h 13m

Chicago Midway

Tue 27/5

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

1 stop5h 20m

C$ 443

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 27/5

6:00 a.m.-12:41 p.m.

1 stop7h 41m

Chicago O'Hare Intl

Tue 3/6

11:07 a.m.-5:40 p.m.

1 stop5h 33m

C$ 446

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/7

12:46 p.m.-9:41 p.m.

1 stop9h 55m

Chicago Midway

Sat 12/7

1:46 p.m.-11:15 p.m.

1 stop8h 29m

C$ 478

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

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.

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 25 April 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 29 April 2025.

It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 8% 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.

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 29 April 2025.

The most flights from YMQ to CHI are scheduled on a Tuesday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 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 29 April 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.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,823 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Crew

8.8

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 320, 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 United Airlines - these airlines can fly you to your destination from C$ 348 and C$ 382, 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$ 195 on Porter Airlines. Other airlines that offer cheap prices include American Airlines from C$ 211 and Air Canada from C$ 218 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: Sun Country Air (100%), Emirates (93%), ANA (91%).

  • 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$ 1,460, our data indicates the cheapest price to be C$ 206. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 302.

  • 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 29 April 2025.
Air Canada flights from Montreal to Chicago
Porter Airlines flights from Montreal to Chicago
United Airlines flights from Montreal to Chicago

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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 332AverageC$ 456FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 349AverageC$ 481FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 356AverageC$ 559FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 381AverageC$ 503FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 442AverageC$ 663FlexibilityNo 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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