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Cheap flights from Montreal to Chicago from C$ 200

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
19 oct. — 26 oct.1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Montreal to Chicago are usually found in March or June, booked 67 days in advance, depart on a Friday or Thursday 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 19 septiembre 2025.

Round-trip from

C$ 327

One-way from

C$ 200

Popular in

November

Cheapest in

March

Average price

C$ 485

Good round-trip deal

C$ 520 or less

Good one-way deal

C$ 449 or less
Porter Airlines
  • Porter Airlines
  • 23/10-26/10
  • 2 total stops
  • 9h 44m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/10
  • 1 total stop
  • 6h 05m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 5% potential increase in price (C$ 36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in September 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 19 septiembre 2025.

sáb. 1/116:15 p.m.YUL - ORD
Nonstop2h 45mAir Canada
sáb. 8/1112:50 p.m.ORD - YUL
Nonstop2h 07mAir Canada
Deal found 17/9C$ 336
vie. 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
mié. 22/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 16/9C$ 338
mié. 8/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
jue. 16/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 17/9C$ 339
jue. 16/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
dom. 19/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 18/9C$ 341
dom. 26/1011:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
mar. 4/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 17/9C$ 342
vie. 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
dom. 19/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 18/9C$ 343
jue. 16/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
lun. 20/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 18/9C$ 345
mié. 15/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
jue. 16/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 17/9C$ 347
mié. 19/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
mar. 25/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 18/9C$ 349
vie. 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
lun. 20/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 16/9C$ 352
mié. 8/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
mié. 15/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 17/9C$ 353
dom. 2/115:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
dom. 9/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 18/9C$ 356

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 19 septiembre 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

jue. 6/11

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

lun. 10/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 334

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 21/11

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

jue. 27/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 335

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 31/10

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

vie. 7/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 336

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb. 22/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 29/11

5:55 p.m.-9:17 p.m.

Nonstop2h 22m

C$ 358

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 16/10

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

Nonstop2h 46m

Chicago O'Hare Intl

jue. 23/10

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

Nonstop2h 29m

C$ 358

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 16/10

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

1 stop4h 14m

Chicago Midway

dom. 19/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 363

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb. 22/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

vie. 28/11

12:50 p.m.-3:57 p.m.

Nonstop2h 07m

C$ 364

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mié. 22/10

9:45 a.m.-11:23 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

jue. 23/10

8:50 a.m.-3:00 p.m.

1 stop5h 10m

C$ 372

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb. 1/11

4:45 p.m.-6:45 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 8/11

8:48 a.m.-3:16 p.m.

1 stop5h 28m

C$ 372

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

vie. 21/11

4:45 p.m.-6:45 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

jue. 27/11

7:15 a.m.-1:28 p.m.

1 stop5h 13m

C$ 372

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/9

Showing 1-10 of 44 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 12 September 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 67 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$ 348). 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 19 septiembre 2025.

It’s optimal to fly from Montreal to Chicago in the afternoon. By choosing this option you can save up to 24% 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 19 septiembre 2025.

The most flights from YMQ to CHI are scheduled on a Tuesday (31 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (30 on average).

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

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 19 septiembre 2025.
Read through reviews of airlines operating flights from Montreal to Chicago, such as Porter Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,926 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,095 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

  • How long is the flight from Montreal to Chicago?

    Airlines like Porter Airlines and United Airlines fly from Montreal to Chicago in about 3h. The time it takes to get you to your destination can typically vary by up to 1h 20m. Montreal and Chicago are separated by a distance of 1199 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    Currently priced at C$ 177, American Airlines will fly you from Montreal to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Porter Airlines and Air Canada - these airlines can fly you to your destination from C$ 202 and C$ 258, respectively. You may be able to fly from Montreal to Chicago for 61% 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$ 200 on Porter Airlines. Other airlines that offer cheap prices include United Airlines from C$ 216 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: Avianca (93%), ANA (93%), Emirates (92%).

  • 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$ 1,536, our data indicates the cheapest price to be C$ 249. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 358.

  • 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$ 348). 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 19 septiembre 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 19 septiembre 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 177AverageC$ 412FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 202AverageC$ 439FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 258AverageC$ 520FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 355AverageC$ 488FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 452AverageC$ 595FlexibilityNo 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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