Cheap flights from Montreal to Chicago from $233!

Roundtrip flight Montreal - Chicago for $233

Flytrippers Deals
Mar 17, 2026
Deals from Montreal

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CHICAGO, Illinois 🇺🇸

$233 (or 23,300 simple points)
	Normal average price: $402 (or 40,200 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

$233

(or 23,300 simple points)

Normal average price: $402 (or 40,200 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 28 - May 5	7d	Tue - Tue	YUL-MDW	$256		Details >	$256 >
Apr 28 - May 12	14d	Tue - Tue	YUL-MDW	$256		Details >	$256 >
Apr 7 - Apr 10	3d	Tue - Fri	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 11	4d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 14	7d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 15	8d	Tue - Wed	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 16	9d	Tue - Thu	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 18	11d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 19	12d	Tue - Sun	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 21	14d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 7 - Apr 22	15d	Tue - Wed	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 14	6d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 15	7d	Wed - Wed	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 19	11d	Wed - Sun	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 21	13d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 22	14d	Wed - Wed	YUL-ORD	$312		Details >	$312 >
Apr 8 - Apr 28	20d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 9 - Apr 14	5d	Thu - Tue	YUL-ORD	$312		Details >	$312 >
Apr 9 - Apr 15	6d	Thu - Wed	YUL-ORD	$312		Details >	$312 >
Apr 10 - Apr 14	4d	Fri - Tue	YUL-ORD	$312		Details >	$312 >
Apr 10 - May 3	23d	Fri - Sun	YUL-ORD	$312		Details >	$312 >
Apr 11 - Apr 14	3d	Sat - Tue	YUL-ORD	$312		Details >	$312 >
Apr 14 - Apr 25	11d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
Apr 14 - Apr 28	14d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 14 - May 1	17d	Tue - Fri	YUL-ORD	$312		Details >	$312 >
Apr 15 - Apr 25	10d	Wed - Sat	YUL-ORD	$312		Details >	$312 >
Apr 15 - Apr 28	13d	Wed - Tue	YUL-ORD	$312		Details >	$312 >
Apr 15 - May 1	16d	Wed - Fri	YUL-ORD	$312		Details >	$312 >
Apr 16 - Apr 25	9d	Thu - Sat	YUL-ORD	$312		Details >	$312 >
Apr 18 - Apr 26	8d	Sat - Sun	YUL-ORD	$312		Details >	$312 >
Apr 19 - Apr 26	7d	Sun - Sun	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 6	13d	Thu - Wed	YUL-ORD	$312		Details >	$312 >
Apr 28 - May 6	8d	Tue - Wed	YUL-ORD	$312		Details >	$312 >
Apr 28 - May 9	11d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
Apr 28 - May 12	14d	Tue - Tue	YUL-ORD	$312		Details >	$312 >
Apr 29 - May 6	7d	Wed - Wed	YUL-ORD	$312		Details >	$312 >
Apr 29 - May 9	10d	Wed - Sat	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			25,600 points instead of $256		Learn more >
Or redeem points of the more simple type (25,600 points instead of $256)				Details >

May 1 - May 5	4d	Fri - Tue	YUL-MDW	$234		Details >	$234 >
May 1 - May 6	5d	Fri - Wed	YUL-MDW	$233		Details >	$233 >
May 1 - May 12	11d	Fri - Tue	YUL-MDW	$233		Details >	$233 >
May 5 - May 12	7d	Tue - Tue	YUL-MDW	$235		Details >	$235 >
May 6 - May 12	6d	Wed - Tue	YUL-MDW	$234		Details >	$234 >
May 6 - May 13	7d	Wed - Wed	YUL-MDW	$235		Details >	$235 >
May 6 - May 26	20d	Wed - Tue	YUL-MDW	$233		Details >	$233 >
May 12 - May 13	1d	Tue - Wed	YUL-MDW	$267		Details >	$267 >
May 12 - Jun 1	20d	Tue - Mon	YUL-MDW	$267		Details >	$267 >
May 20 - May 26	6d	Wed - Tue	YUL-MDW	$236		Details >	$236 >
May 20 - Jun 1	12d	Wed - Mon	YUL-MDW	$236		Details >	$236 >
May 26 - Jun 1	6d	Tue - Mon	YUL-MDW	$249		Details >	$249 >
May 26 - Jun 2	7d	Tue - Tue	YUL-MDW	$262		Details >	$262 >
May 1 - May 9	8d	Fri - Sat	YUL-ORD	$312		Details >	$312 >
May 2 - May 9	7d	Sat - Sat	YUL-ORD	$312		Details >	$312 >
May 5 - May 23	18d	Tue - Sat	YUL-ORD	$312		Details >	$312 >
May 6 - May 23	17d	Wed - Sat	YUL-ORD	$312		Details >	$312 >
May 7 - May 23	16d	Thu - Sat	YUL-ORD	$312		Details >	$312 >
May 18 - May 25	7d	Mon - Mon	YUL-ORD	$312		Details >	$312 >
May 19 - May 25	6d	Tue - Mon	YUL-ORD	$312		Details >	$312 >
May 20 - May 25	5d	Wed - Mon	YUL-ORD	$312		Details >	$312 >
Or redeem points of the more simple type			23,300 points instead of $233		Learn more >
Or redeem points of the more simple type (23,300 points instead of $233)				Details >

Jun 1 - Jun 8	7d	Mon - Mon	YUL-MDW	$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

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