Cheap flights from Montreal to Chicago from $261!

Roundtrip flight Montreal - Chicago for $261

Flytrippers Deals
Nov 10, 2025
Deals from Montreal

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CHICAGO, Illinois 🇺🇸

$261 (or 26,100 simple points)
	Normal average price: $408 (or 40,800 simple points)
	Roundtrip, all taxes/fees included
	FROM: YUL - Montréal-Trudeau International Airport
	TO: ORD - O'Hare International Airport
	See all available dates

$261

(or 26,100 simple points)

Normal average price: $408 (or 40,800 simple points)

Roundtrip, all taxes/fees included

FROM: YUL - Montréal-Trudeau International Airport

TO: ORD - O'Hare International Airport

See all available dates

IMPORTANT WARNING ABOUT THIS DEAL

Limited carry-on ⌄

￫ At least one of the date combinations in this flight deal is with an airline that charge extra for to bring a standard carry-on on board. You will always be allowed a smaller personal item for free.

🔎 Pro tip: Always check if the flight price is the same on the airline's direct website before booking!

DATES

Deals expire quickly; act fast! Click here for more details.

Feb 24 - Mar 2	6d	Tue - Mon	$261		Details >	$261 >
Feb 24 - Mar 3	7d	Tue - Tue	$261		Details >	$261 >
Feb 24 - Mar 4	8d	Tue - Wed	$261		Details >	$261 >
Feb 24 - Mar 10	14d	Tue - Tue	$261		Details >	$261 >
Feb 24 - Mar 11	15d	Tue - Wed	$261		Details >	$261 >
Or redeem points of the more simple type			26,100 points instead of $261		Learn more >
Or redeem points of the more simple type (26,100 points instead of $261)				Details >

Mar 3 - Mar 10	7d	Tue - Tue	$261		Details >	$261 >
Mar 3 - Mar 17	14d	Tue - Tue	$261		Details >	$261 >
Mar 4 - Mar 11	7d	Wed - Wed	$261		Details >	$261 >
Mar 10 - Mar 24	14d	Tue - Tue	$261		Details >	$261 >
Mar 11 - Mar 25	14d	Wed - Wed	$261		Details >	$261 >
Mar 17 - Mar 31	14d	Tue - Tue	$261		Details >	$261 >
Mar 17 - Apr 7	21d	Tue - Tue	$261		Details >	$261 >
Mar 18 - Apr 1	14d	Wed - Wed	$261		Details >	$261 >
Mar 22 - Apr 12	21d	Sun - Sun	$261		Details >	$261 >
Mar 31 - Apr 14	14d	Tue - Tue	$261		Details >	$261 >
Or redeem points of the more simple type			26,100 points instead of $261		Learn more >
Or redeem points of the more simple type (26,100 points instead of $261)				Details >

Apr 1 - Apr 15	14d	Wed - Wed	$261		Details >	$261 >
Apr 14 - Apr 21	7d	Tue - Tue	$261		Details >	$261 >
Apr 14 - Apr 28	14d	Tue - Tue	$261		Details >	$261 >
Apr 17 - Apr 20	3d	Fri - Mon	$261		Details >	$261 >
Apr 17 - Apr 21	4d	Fri - Tue	$261		Details >	$261 >
Apr 17 - Apr 22	5d	Fri - Wed	$261		Details >	$261 >
Apr 17 - Apr 27	10d	Fri - Mon	$261		Details >	$261 >
Apr 17 - Apr 28	11d	Fri - Tue	$261		Details >	$261 >
Apr 17 - Apr 29	12d	Fri - Wed	$261		Details >	$261 >
Apr 17 - May 2	15d	Fri - Sat	$261		Details >	$261 >
Apr 17 - May 3	16d	Fri - Sun	$261		Details >	$261 >
Apr 17 - May 5	18d	Fri - Tue	$261		Details >	$261 >
Apr 17 - May 6	19d	Fri - Wed	$261		Details >	$261 >
Apr 19 - May 3	14d	Sun - Sun	$261		Details >	$261 >
Apr 20 - Apr 26	6d	Mon - Sun	$261		Details >	$261 >
Apr 20 - Apr 27	7d	Mon - Mon	$261		Details >	$261 >
Apr 21 - Apr 27	6d	Tue - Mon	$261		Details >	$261 >
Apr 21 - Apr 28	7d	Tue - Tue	$261		Details >	$261 >
Apr 21 - Apr 29	8d	Tue - Wed	$261		Details >	$261 >
Apr 21 - May 2	11d	Tue - Sat	$261		Details >	$261 >
Apr 21 - May 3	12d	Tue - Sun	$261		Details >	$261 >
Apr 21 - May 5	14d	Tue - Tue	$261		Details >	$261 >
Apr 21 - May 6	15d	Tue - Wed	$261		Details >	$261 >
Apr 22 - Apr 29	7d	Wed - Wed	$261		Details >	$261 >
Apr 22 - May 2	10d	Wed - Sat	$261		Details >	$261 >
Apr 27 - May 18	21d	Mon - Mon	$261		Details >	$261 >
Apr 28 - May 12	14d	Tue - Tue	$261		Details >	$261 >
Apr 29 - May 13	14d	Wed - Wed	$261		Details >	$261 >
Or redeem points of the more simple type			26,100 points instead of $261		Learn more >
Or redeem points of the more simple type (26,100 points instead of $261)				Details >

May 2 - May 11	9d	Sat - Mon	$261		Details >	$261 >
May 3 - May 24	21d	Sun - Sun	$261		Details >	$261 >
May 5 - May 19	14d	Tue - Tue	$261		Details >	$261 >
May 6 - May 20	14d	Wed - Wed	$261		Details >	$261 >
May 12 - May 22	10d	Tue - Fri	$261		Details >	$261 >
May 12 - May 26	14d	Tue - Tue	$261		Details >	$261 >
May 13 - May 27	14d	Wed - Wed	$261		Details >	$261 >
May 14 - May 22	8d	Thu - Fri	$261		Details >	$261 >
Or redeem points of the more simple type			26,100 points instead of $261		Learn more >
Or redeem points of the more simple type (26,100 points instead of $261)				Details >

Might not be a deal, but at least find the lowest price for your specific dates

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DIR Non-stop flight

Dates for weekend getaway

Very limited dates at this price

Flight at an even more discounted price than usual!

Flytrippers logo in a flag Lowest price we have ever seen!

ULCC Involves at least 1 ultra low-cost carrier (ULCC)

No Suitcase Involves at least 1 airline without free regular carry-on bags

V Calendar Dates available during a popular vacation period

Self-transfer that implies a few pecularities

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Featured image:

Other images associated with this deal: Main page: Pixabay, Social media: Pixabay

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CHICAGO, Illinois 🇺🇸

IMPORTANT WARNING ABOUT THIS DEAL

DATES

Accommodation Options

Sign up for our free newsletter

Check out today's best deals from Montreal

Our latest travel content

Travel News

Flytrippers interviewed on the TV news about the US shutdown’s flight cancellations

Thousands of flight cancellations coming this weekend?

Canada gets North America’s 1st route to this exciting African coastal destination

Travel Rewards

Promotion for VIPorter points redemptions: 25% discount on Porter and Air Transat flights

15 travel rewards updates (roundup post)

It’s back: Bonus of 20 pts/$ (≈ 30%) on quality bedding products made in Canada (I love them)

Follow Flytrippers on Facebook

Follow Flytrippers on Twitter

Canada gets North America’s 1^st route to this exciting African coastal destination