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Cheap flights from Montreal to Chicago from C$ 221

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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
22 Jan — 29 Jan1
1 adult

The best prices from Montreal to Chicago are usually found in February or March, booked 83 days in advance, depart on a Wednesday or Friday and return on a Tuesday

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 17 January 2025.

Round-trip from

C$ 435

One-way from

C$ 221

Popular in

November

Cheapest in

February

Average price

C$ 494
Porter Airlines
  • Porter Airlines
  • 10/4-14/4
  • 2 total stops
  • 10h 15m total
  • Montreal to Chicago
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11/2
  • 11/2
  • 1 total stop
  • 8h 37m total
  • Montreal to Chicago
Search Deals
High demand for flights, 5% potential price rise
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Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in January 2025
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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 17 January 2025.

Thu 10/46:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Mon 14/411:15 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 16/1C$ 435
Wed 19/23:55 p.m.YUL - ORD
1 stop9h 03mMultiple Airlines
Tue 25/27:10 a.m.ORD - YUL
1 stop9h 25mMultiple Airlines
Deal found 15/1C$ 441
Thu 3/49:45 a.m.YUL - ORD
Nonstop2h 47mUnited Airlines
Mon 7/41:55 p.m.ORD - YUL
Nonstop2h 31mUnited Airlines
Deal found 16/1C$ 523
Tue 18/26:20 p.m.YUL - ORD
Nonstop2h 35mAir Canada
Tue 25/27:20 a.m.ORD - YUL
Nonstop2h 12mAir Canada
Deal found 16/1C$ 532
Mon 24/25:35 p.m.YUL - ORD
1 stop16h 13mAmerican Airlines
Thu 27/210:37 a.m.ORD - YUL
1 stop5h 18mAmerican Airlines
Deal found 16/1C$ 552
Thu 6/28:55 a.m.YUL - MDW
1 stop4h 15mMultiple Airlines
Sun 9/21:05 p.m.MDW - YUL
1 stop10h 34mMultiple Airlines
Deal found 16/1C$ 559
Fri 18/46:00 p.m.YUL - ORD
1 stop7h 06mDelta
Sun 20/47:00 a.m.ORD - YUL
1 stop8h 02mDelta
Deal found 16/1C$ 578
Mon 10/27:05 a.m.YUL - MDW
1 stop7h 00mDelta
Tue 11/25:05 p.m.MDW - YUL
1 stop5h 47mDelta
Deal found 16/1C$ 578
Thu 20/26:45 a.m.YUL - ORD
2 stops16h 51mWestJet
Mon 24/24:45 p.m.ORD - YUL
2 stops18h 45mWestJet
Deal found 15/1C$ 598
Fri 29/86:15 p.m.YUL - MDW
1 stop24h 48mWestJet
Tue 2/92:00 p.m.MDW - YUL
1 stop8h 18mWestJet
Deal found 16/1C$ 644

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 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/4

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

1 stop4h 30m

Chicago Midway

Mon 14/4

11:15 a.m.-6:00 p.m.

1 stop5h 45m

C$ 435

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 19/2

3:55 p.m.-11:58 p.m.

1 stop9h 03m

Chicago O'Hare Intl

Tue 25/2

7:10 a.m.-5:35 p.m.

1 stop9h 25m

C$ 441

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 3/4

6:15 a.m.-8:02 a.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sun 6/4

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

Nonstop2h 16m

C$ 523

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 18/2

6:20 p.m.-7:55 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Tue 25/2

7:20 a.m.-10:32 a.m.

Nonstop2h 12m

C$ 532

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 24/2

5:35 p.m.-8:48 a.m.

1 stop16h 13m

Chicago O'Hare Intl

Thu 27/2

10:37 a.m.-4:55 p.m.

1 stop5h 18m

C$ 552

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 6/2

8:55 a.m.-12:10 p.m.

1 stop4h 15m

Chicago Midway

Sun 9/2

1:05 p.m.-12:39 a.m.

1 stop10h 34m

C$ 559

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 20/2

11:20 a.m.-4:09 p.m.

1 stop5h 49m

Chicago O'Hare Intl

Mon 24/2

4:45 p.m.-3:36 p.m.

1 stop21h 51m

C$ 562

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 18/4

6:00 p.m.-12:06 a.m.

1 stop7h 06m

Chicago O'Hare Intl

Sun 20/4

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

1 stop8h 02m

C$ 578

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 10/2

7:05 a.m.-1:05 p.m.

1 stop7h 00m

Chicago Midway

Tue 11/2

5:05 p.m.-11:52 p.m.

1 stop5h 47m

C$ 578

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 10/2

6:45 a.m.-10:12 a.m.

2 stops28h 27m

Chicago Midway

Tue 11/2

12:44 p.m.-11:52 p.m.

1 stop10h 08m

C$ 691

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

Showing 1-10 of 20 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 10 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 83 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 17 January 2025.

It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 27% 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 Saturday afternoons 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 17 January 2025.

The most flights from YMQ to CHI are scheduled on a Wednesday (16 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 17 January 2025.
Get a feel of what it's like to fly with WestJet, United Airlines and Delta 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
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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

Delta
8.0
Very good
8,511 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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

United Airlines
7.4
Good
8,965 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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

WestJet
7.2
Good
2,824 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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$ 435, 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 American Airlines and United Airlines - these airlines can fly you to your destination from C$ 446 and C$ 523, respectively. You may be able to fly from Montreal to Chicago for 12% 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$ 223 on Porter Airlines. Other airlines that offer cheap prices include United Airlines from C$ 299 and Air Canada from C$ 303 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: Alaska Airlines (91%), Avianca (87%), ANA (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$ 1,462, our data indicates the cheapest price to be C$ 230. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 447.

  • 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 17 January 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 17 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 330AverageC$ 472FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 370AverageC$ 596FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 371AverageC$ 419FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 372AverageC$ 520FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 395AverageC$ 521FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 459AverageC$ 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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