Cheap flights from Montreal to Chicago from $247!

Roundtrip flight Montreal - Chicago for $247

Flytrippers Deals
Mar 21, 2026
Deals from Montreal

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CHICAGO, Illinois 🇺🇸

$247 (or 24,700 simple points)
	Normal average price: $405 (or 40,500 simple points)
	Roundtrip, all taxes/fees included
	FROM: YUL - Montréal-Trudeau International Airport
	TO: MDW - Chicago Midway International Airport ORD - O'Hare International Airport
	See all available dates

$247

(or 24,700 simple points)

Normal average price: $405 (or 40,500 simple points)

Roundtrip, all taxes/fees included

FROM: YUL - Montréal-Trudeau International Airport

TO:
MDW - Chicago Midway International Airport
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.

Apr 11 - Apr 21	10d	Sat - Tue	YUL-ORD	$313		Details >	$313 >
Apr 14 - Apr 19	5d	Tue - Sun	YUL-ORD	$312		Details >	$312 >
Apr 14 - Apr 21	7d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 14 - Apr 22	8d	Tue - Wed	YUL-ORD	$312		Details >	$312 >
Apr 14 - Apr 25	11d	Tue - Sat	YUL-ORD	$313		Details >	$313 >
Apr 14 - Apr 28	14d	Tue - Tue	YUL-ORD	$313		Details >	$313 >
Apr 14 - May 12	28d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 15 - Apr 21	6d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 15 - Apr 22	7d	Wed - Wed	YUL-ORD	$312		Details >	$312 >
Apr 15 - Apr 28	13d	Wed - Tue	YUL-ORD	$313		Details >	$313 >
Apr 15 - May 5	20d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 16 - Apr 22	6d	Thu - Wed	YUL-ORD	$313		Details >	$313 >
Apr 18 - May 2	14d	Sat - Sat	YUL-ORD	$313		Details >	$313 >
Apr 18 - May 12	24d	Sat - Tue	YUL-ORD	$313		Details >	$313 >
Apr 19 - May 2	13d	Sun - Sat	YUL-ORD	$312		Details >	$312 >
Apr 21 - May 5	14d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 21 - May 6	15d	Tue - Wed	YUL-ORD	$312		Details >	$312 >
Apr 22 - May 5	13d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 22 - May 6	14d	Wed - Wed	YUL-ORD	$312		Details >	$312 >
Apr 23 - May 5	12d	Thu - Tue	YUL-ORD	$312		Details >	$312 >
Apr 23 - May 6	13d	Thu - Wed	YUL-ORD	$312		Details >	$312 >
Apr 24 - May 4	10d	Fri - Mon	YUL-ORD	$313		Details >	$313 >
Apr 24 - May 5	11d	Fri - Tue	YUL-ORD	$312		Details >	$312 >
Apr 24 - May 17	23d	Fri - Sun	YUL-ORD	$312		Details >	$312 >
Apr 25 - May 4	9d	Sat - Mon	YUL-ORD	$313		Details >	$313 >
Apr 25 - May 5	10d	Sat - Tue	YUL-ORD	$312		Details >	$312 >
Apr 28 - May 5	7d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 28 - May 12	14d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 29 - May 5	6d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 29 - May 12	13d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Or redeem points of the more simple type			31,200 points instead of $312		Learn more >
Or redeem points of the more simple type (31,200 points instead of $312)				Details >

May 8 - Jun 1	24d	Fri - Mon	YUL-MDW	$247		Details >	$247 >
May 5 - May 12	7d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
May 5 - May 26	21d	Tue - Tue	YUL-ORD	$313		Details >	$313 >
May 5 - May 30	25d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
May 6 - May 12	6d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
May 6 - May 26	20d	Wed - Tue	YUL-ORD	$313		Details >	$313 >
May 6 - May 27	21d	Wed - Wed	YUL-ORD	$313		Details >	$313 >
May 7 - May 12	5d	Thu - Tue	YUL-ORD	$312		Details >	$312 >
May 7 - May 26	19d	Thu - Tue	YUL-ORD	$313		Details >	$313 >
May 8 - May 26	18d	Fri - Tue	YUL-ORD	$313		Details >	$313 >
May 11 - May 27	16d	Mon - Wed	YUL-ORD	$313		Details >	$313 >
May 12 - May 27	15d	Tue - Wed	YUL-ORD	$313		Details >	$313 >
May 13 - May 27	14d	Wed - Wed	YUL-ORD	$313		Details >	$313 >
May 19 - May 27	8d	Tue - Wed	YUL-ORD	$313		Details >	$313 >
May 19 - May 29	10d	Tue - Fri	YUL-ORD	$313		Details >	$313 >
May 20 - May 27	7d	Wed - Wed	YUL-ORD	$313		Details >	$313 >
May 20 - May 29	9d	Wed - Fri	YUL-ORD	$313		Details >	$313 >
May 21 - May 27	6d	Thu - Wed	YUL-ORD	$313		Details >	$313 >
May 21 - May 29	8d	Thu - Fri	YUL-ORD	$313		Details >	$313 >
Or redeem points of the more simple type			24,700 points instead of $247		Learn more >
Or redeem points of the more simple type (24,700 points instead of $247)				Details >

Jun 1 - Jun 5	4d	Mon - Fri	YUL-MDW	$249		Details >	$249 >
Jun 1 - Jun 8	7d	Mon - Mon	YUL-MDW	$249		Details >	$249 >
Or redeem points of the more simple type			24,900 points instead of $249		Learn more >
Or redeem points of the more simple type (24,900 points instead of $249)				Details >

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

Check out our flight search tips and more tools here

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

Deals powered by Skyscanner, Momondo, Kiwi & Kayak

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Featured image:

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

Share this deal to help us help more people travel for less:

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

LCN interviewed Flytrippers: Disrupted flights in the Middle East and Mexico

Now in effect: Strict enforcement of the UK Electronic Travel Authorisation requirement (UK ETA)

Air Transat will cancel all of its Canada–US routes

Travel Rewards

Marriott Bonvoy free night certificates: Ultimate guide (2026)

Marriott Bonvoy promotion (Winter 2026): Bonus of 1 elite night per brand and 2,500 points per stay

WOW: New record-high offer on the only card that every Canadian traveler must have (no exceptions possible)

Follow Flytrippers on Facebook

Follow Flytrippers on Twitter