Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Montreal to Chicago from C$ 191

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 21/5. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — CHI
16 Apr — 23 Apr1
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 11 April 2025.

Round-trip from

C$ 336

One-way from

C$ 191

Popular in

November

Cheapest in

March

Average price

C$ 497

Good round-trip deal

C$ 512 or less

Good one-way deal

C$ 341 or less
Porter Airlines
  • Porter Airlines
  • 12/5-16/5
  • 2 total stops
  • 12h 29m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 21/5
  • 1 total stop
  • 7h 09m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Montreal (YMQ) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Montreal (YMQ) to Chicago (CHI).
Search Deals

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 11 April 2025.

Mon 12/510:45 a.m.YUL - MDW
1 stop7h 09mPorter Airlines
Fri 16/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 10/4C$ 336
Mon 26/58:20 a.m.YUL - ORD
Nonstop2h 32mAir Canada
Mon 2/68:25 p.m.ORD - YUL
1 stop4h 26mAir Canada
Deal found 10/4C$ 341
Thu 1/59:45 a.m.YUL - ORD
Nonstop2h 47mLufthansa
Sun 4/51:55 p.m.ORD - YUL
Nonstop2h 31mLufthansa
Deal found 10/4C$ 375
Thu 22/56:15 a.m.YUL - ORD
Nonstop2h 44mUnited Airlines
Sun 25/57:10 a.m.ORD - YUL
1 stop15h 16mUnited Airlines
Deal found 10/4C$ 380
Fri 9/512:44 p.m.YUL - ORD
1 stop9h 36mDelta
Tue 13/52:45 p.m.ORD - YUL
1 stop5h 24mDelta
Deal found 10/4C$ 389
Thu 1/57:10 a.m.YUL - MDW
1 stop6h 25mDelta
Tue 6/53:02 p.m.MDW - YUL
1 stop7h 26mDelta
Deal found 10/4C$ 389
Wed 14/58:30 a.m.YUL - ORD
1 stop7h 44mMultiple Airlines
Wed 11/66:15 p.m.ORD - YUL
1 stop14h 35mMultiple Airlines
Deal found 10/4C$ 414
Fri 16/56:45 p.m.YUL - ORD
1 stop21h 21mWestJet
Fri 23/57:25 p.m.ORD - YUL
1 stop26h 51mWestJet
Deal found 10/4C$ 459
Thu 24/412:30 p.m.YUL - ORD
Nonstop2h 35mAmerican Airlines
Mon 28/48:30 p.m.ORD - YUL
1 stop12h 20mAmerican Airlines
Deal found 9/4C$ 461
Sat 17/52:50 p.m.YUL - MDW
1 stop7h 24mMultiple Airlines
Tue 20/55:20 p.m.MDW - YUL
1 stop3h 55mMultiple Airlines
Deal found 10/4C$ 462
Wed 21/56:15 a.m.YUL - MDW
1 stop8h 00mWestJet
Sun 25/59:20 a.m.MDW - YUL
2 stops20h 48mWestJet
Deal found 10/4C$ 487

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 11 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

Mon 12/5

10:45 a.m.-4:54 p.m.

1 stop7h 09m

Chicago Midway

Fri 16/5

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

1 stop5h 20m

C$ 336

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 26/5

8:20 a.m.-9:52 a.m.

Nonstop2h 32m

Chicago O'Hare Intl

Mon 2/6

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

1 stop4h 26m

C$ 341

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 1/5

9:45 a.m.-11:32 a.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sun 4/5

1:55 p.m.-5:26 p.m.

Nonstop2h 31m

C$ 375

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 22/5

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

Nonstop2h 44m

Chicago O'Hare Intl

Sun 25/5

7:10 a.m.-11:26 p.m.

1 stop15h 16m

C$ 380

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 9/5

6:00 a.m.-9:51 a.m.

1 stop4h 51m

Chicago O'Hare Intl

Sat 10/5

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

1 stop8h 31m

C$ 389

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 1/5

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

1 stop6h 25m

Chicago Midway

Tue 6/5

3:02 p.m.-11:28 p.m.

1 stop7h 26m

C$ 389

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 14/5

8:30 a.m.-3:14 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Wed 11/6

6:15 p.m.-9:50 a.m.

1 stop14h 35m

C$ 414

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 16/5

6:45 p.m.-3:06 p.m.

1 stop21h 21m

Chicago O'Hare Intl

Fri 23/5

7:25 p.m.-11:16 p.m.

1 stop26h 51m

C$ 459

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 24/4

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

Nonstop2h 35m

Chicago O'Hare Intl

Mon 28/4

8:30 p.m.-9:50 a.m.

1 stop12h 20m

C$ 461

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 17/5

2:50 p.m.-9:14 p.m.

1 stop7h 24m

Chicago Midway

Tue 20/5

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

1 stop3h 55m

C$ 462

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 22 results
1
2
3

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 4 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 11 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 11 April 2025.

The most flights from YMQ to CHI are scheduled on a Wednesday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 11 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
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
280 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,910 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
United Airlines
7.4
Good
8,636 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
WestJet
7.2
Good
2,802 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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$ 336, 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 Lufthansa - these airlines can fly you to your destination from C$ 341 and C$ 375, respectively. You may be able to fly from Montreal to Chicago for 30% 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$ 191 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from C$ 194 and American Airlines from C$ 201 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%), ANA (93%), Emirates (93%).

  • 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$ 1,743, our data indicates the cheapest price to be C$ 228. The most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), is priced around C$ 345.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 11 April 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 11 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 336AverageC$ 462FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 354AverageC$ 488FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 361AverageC$ 572FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 363AverageC$ 483FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 386AverageC$ 509FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 448AverageC$ 608FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.