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Cheap flights from Montreal to Chicago from C$ 199

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 29/8. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
2 Aug — 9 Aug1
1 adult

Cheapflights Tip: The best prices from Montreal to Chicago are usually found in March or June, booked 85 days in advance, depart on a Friday or Thursday and return on a Monday

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 28 July 2025.

Round-trip from

C$ 237

One-way from

C$ 199

Popular in

November

Cheapest in

March

Average price

C$ 508

Good round-trip deal

C$ 537 or less

Good one-way deal

C$ 355 or less
Air Canada
  • Air Canada
  • 11/9-18/9
  • 1 total stop
  • 6h 56m total
  • Montreal to Chicago
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Air Canada
  • Air Canada
  • 29/8
  • Nonstop
  • 2h 46m 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$ 12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 28 July 2025.

Thu 11/98:20 a.m.YUL - ORD
Nonstop2h 31mAir Canada
Thu 18/98:25 p.m.ORD - YUL
1 stop4h 25mAir Canada
Deal found 28/7C$ 237
Tue 26/85:29 p.m.YUL - ORD
Nonstop2h 36mAmerican Airlines
Mon 1/95:20 a.m.ORD - YUL
1 stop7h 19mAmerican Airlines
Deal found 27/7C$ 238
Fri 17/1010:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Sat 25/109:35 a.m.MDW - YUL
1 stop7h 20mPorter Airlines
Deal found 27/7C$ 240
Sat 30/88:15 a.m.YUL - ORD
2 stops10h 27mMultiple Airlines
Sun 31/88:10 a.m.ORD - YUL
Nonstop2h 26mMultiple Airlines
Deal found 27/7C$ 260
Wed 5/119:28 a.m.YUL - ORD
1 stop7h 43mDelta
Wed 12/1110:35 a.m.ORD - YUL
1 stop4h 25mDelta
Deal found 27/7C$ 296
Sat 30/82:48 p.m.YUL - MDW
1 stop7h 24mDelta
Wed 3/91:43 p.m.MDW - YUL
1 stop8h 33mDelta
Deal found 26/7C$ 296
Sat 23/84:55 p.m.YUL - ORD
Nonstop2h 46mUnited Airlines
Sat 30/86:00 p.m.ORD - YUL
Nonstop2h 29mUnited Airlines
Deal found 27/7C$ 362
Fri 10/1012:36 p.m.YUL - MDW
1 stop10h 38mMultiple Airlines
Sun 12/105:20 p.m.MDW - YUL
1 stop3h 55mMultiple Airlines
Deal found 27/7C$ 362
Thu 21/86:15 a.m.YUL - ORD
Nonstop2h 46mLufthansa
Sun 24/87:11 a.m.ORD - YUL
Nonstop2h 29mLufthansa
Deal found 28/7C$ 382

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 28 July 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

Thu 11/9

8:20 a.m.-9:51 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Thu 18/9

8:25 p.m.-1:50 a.m.

1 stop4h 25m

C$ 237

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 26/8

5:29 p.m.-7:05 p.m.

Nonstop2h 36m

Chicago O'Hare Intl

Mon 1/9

5:20 a.m.-1:39 p.m.

1 stop7h 19m

C$ 238

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

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

1 stop6h 39m

Chicago Midway

Sat 25/10

9:35 a.m.-5:55 p.m.

1 stop7h 20m

C$ 240

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 30/8

8:15 a.m.-5:42 p.m.

2 stops10h 27m

Chicago O'Hare Intl

Sun 31/8

8:10 a.m.-11:36 a.m.

Nonstop2h 26m

C$ 260

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 5/11

9:28 a.m.-4:11 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Wed 12/11

10:35 a.m.-4:00 p.m.

1 stop4h 25m

C$ 296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 30/8

6:00 a.m.-12:28 p.m.

1 stop7h 28m

Chicago Midway

Wed 3/9

4:25 p.m.-11:53 p.m.

1 stop6h 28m

C$ 296

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 23/8

4:55 p.m.-6:41 p.m.

Nonstop2h 46m

Chicago O'Hare Intl

Sat 30/8

6:00 p.m.-9:29 p.m.

Nonstop2h 29m

C$ 362

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/10

12:36 p.m.-10:14 p.m.

1 stop10h 38m

Chicago Midway

Sun 12/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 362

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 21/8

6:15 a.m.-8:01 a.m.

Nonstop2h 46m

Chicago O'Hare Intl

Sun 24/8

7:11 a.m.-10:40 a.m.

Nonstop2h 29m

C$ 382

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 29/8

6:15 a.m.-8:01 a.m.

Nonstop2h 46m

C$ 199

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/7

Showing 1-10 of 19 results
1
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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 July 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 85 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$ 352). 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 28 July 2025.

It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 19% 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 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 28 July 2025.

The most flights from YMQ to CHI are scheduled on a Monday (31 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (29 on average).

How much does it cost to fly round-trip from Montreal to Chicago?

What’s the top layover airport for flights from Montreal to Chicago?

Share of one-stop round-trip flights from Montreal to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YTZ) – chosen by Cheapflights users on 90% of one-stop itineraries from Montreal to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Montreal to Chicago?

Average round-trip fare for 1-stop flights from Montreal to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 354.

What’s the fastest layover option from Montreal to Chicago?

Shortest average travel time for 1-stop one-way flights from Montreal to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 2h 06m.

Which airport typically offers the quickest layover for flights from Montreal to Chicago?

Average layover duration for 1-stop one-way flights from Montreal to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via New York (LGA) offer the fastest connection on this route, with an average layover time of 0h 57m.

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 28 July 2025.
Read through reviews of airlines operating flights from Montreal to Chicago, such as Porter Airlines,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
316 reviews
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,975 reviews
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,892 reviews
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,968 reviews
Porter Airlines
8.0
Very good
316 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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$ 237, 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 American Airlines and Porter Airlines - these airlines can fly you to your destination from C$ 238 and C$ 240, respectively. You may be able to fly from Montreal to Chicago for 48% 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$ 199 on Air Canada. Other airlines that offer cheap prices include Porter Airlines from C$ 199 and United Airlines 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: Qantas Airways (95%), Qatar Airways (93%), Emirates (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$ 1,552, our data indicates the cheapest price to be C$ 216. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 248.

  • 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$ 352). 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

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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 28 July 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 28 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 201AverageC$ 435FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 240AverageC$ 460FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 291AverageC$ 529FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 345AverageC$ 482FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 449AverageC$ 656FlexibilityNo 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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