Cheap flights from Montreal to Chicago from $171!

Roundtrip flight Montreal - Chicago for $171

Flytrippers Deals
Jul 9, 2025
Deals from Montreal

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CHICAGO, Illinois 🇺🇸

$171
	Normal average price: $417 (or 41,700 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

$171
	Normal average price: $417 (or 41,700 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.

4 Sep - 7 Sep	3d	Thu - Sun	YUL-MDW	$171	Details >	$171 >
4 Sep - 18 Sep	14d	Thu - Thu	YUL-MDW	$171	Details >	$171 >
4 Sep - 25 Sep	21d	Thu - Thu	YUL-MDW	$171	Details >	$171 >
8 Sep - 15 Sep	7d	Mon - Mon	YUL-MDW	$179	Details >	$179 >
9 Sep - 16 Sep	7d	Tue - Tue	YUL-MDW	$178	Details >	$178 >
9 Sep - 23 Sep	14d	Tue - Tue	YUL-MDW	$177	Details >	$177 >
10 Sep - 17 Sep	7d	Wed - Wed	YUL-MDW	$178	Details >	$178 >
11 Sep - 25 Sep	14d	Thu - Thu	YUL-MDW	$177	Details >	$177 >
16 Sep - 30 Sep	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
17 Sep - 1 Oct	14d	Wed - Wed	YUL-MDW	$176	Details >	$176 >
23 Sep - 7 Oct	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
23 Sep - 14 Oct	21d	Tue - Tue	YUL-MDW	$175	Details >	$175 >
24 Sep - 8 Oct	14d	Wed - Wed	YUL-MDW	$179	Details >	$179 >
30 Sep - 7 Oct	7d	Tue - Tue	YUL-MDW	$179	Details >	$179 >
30 Sep - 14 Oct	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
17 Sep - 8 Oct	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
23 Sep - 30 Sep	7d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
23 Sep - 7 Oct	14d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
25 Sep - 28 Sep	3d	Thu - Sun	YUL-ORD	$239	Details >	$239 >
30 Sep - 7 Oct	7d	Tue - Tue	YUL-ORD	$239	Details >	$239 >

1 Oct - 8 Oct	7d	Wed - Wed	YUL-MDW	$179	Details >	$179 >
7 Oct - 14 Oct	7d	Tue - Tue	YUL-MDW	$177	Details >	$177 >
7 Oct - 21 Oct	14d	Tue - Tue	YUL-MDW	$179	Details >	$179 >
8 Oct - 15 Oct	7d	Wed - Wed	YUL-MDW	$181	Details >	$181 >
14 Oct - 28 Oct	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
15 Oct - 29 Oct	14d	Wed - Wed	YUL-MDW	$179	Details >	$179 >
20 Oct - 30 Oct	10d	Mon - Thu	YUL-MDW	$183	Details >	$183 >
21 Oct - 29 Oct	8d	Tue - Wed	YUL-MDW	$181	Details >	$181 >
21 Oct - 4 Nov	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
22 Oct - 5 Nov	14d	Wed - Wed	YUL-MDW	$176	Details >	$176 >
23 Oct - 1 Nov	9d	Thu - Sat	YUL-MDW	$181	Details >	$181 >
24 Oct - 1 Nov	8d	Fri - Sat	YUL-MDW	$181	Details >	$181 >
30 Oct - 5 Nov	6d	Thu - Wed	YUL-MDW	$182	Details >	$182 >
1 Oct - 8 Oct	7d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
6 Oct - 20 Oct	14d	Mon - Mon	YUL-ORD	$239	Details >	$239 >
7 Oct - 21 Oct	14d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
7 Oct - 1 Nov	25d	Tue - Sat	YUL-ORD	$239	Details >	$239 >
8 Oct - 22 Oct	14d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
8 Oct - 30 Oct	22d	Wed - Thu	YUL-ORD	$239	Details >	$239 >
15 Oct - 23 Oct	8d	Wed - Thu	YUL-ORD	$239	Details >	$239 >
15 Oct - 27 Oct	12d	Wed - Mon	YUL-ORD	$239	Details >	$239 >
15 Oct - 28 Oct	13d	Wed - Tue	YUL-ORD	$239	Details >	$239 >
15 Oct - 29 Oct	14d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
15 Oct - 5 Nov	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
15 Oct - 8 Nov	24d	Wed - Sat	YUL-ORD	$239	Details >	$239 >
16 Oct - 24 Oct	8d	Thu - Fri	YUL-ORD	$239	Details >	$239 >
17 Oct - 31 Oct	14d	Fri - Fri	YUL-ORD	$239	Details >	$239 >
20 Oct - 26 Oct	6d	Mon - Sun	YUL-ORD	$239	Details >	$239 >
21 Oct - 29 Oct	8d	Tue - Wed	YUL-ORD	$239	Details >	$239 >
21 Oct - 11 Nov	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
21 Oct - 12 Nov	22d	Tue - Wed	YUL-ORD	$239	Details >	$239 >
21 Oct - 14 Nov	24d	Tue - Fri	YUL-ORD	$239	Details >	$239 >
22 Oct - 29 Oct	7d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
22 Oct - 12 Nov	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
24 Oct - 1 Nov	8d	Fri - Sat	YUL-ORD	$239	Details >	$239 >
25 Oct - 14 Nov	20d	Sat - Fri	YUL-ORD	$239	Details >	$239 >
27 Oct - 12 Nov	16d	Mon - Wed	YUL-ORD	$239	Details >	$239 >
28 Oct - 31 Oct	3d	Tue - Fri	YUL-ORD	$239	Details >	$239 >
28 Oct - 3 Nov	6d	Tue - Mon	YUL-ORD	$239	Details >	$239 >
28 Oct - 5 Nov	8d	Tue - Wed	YUL-ORD	$239	Details >	$239 >
28 Oct - 18 Nov	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
28 Oct - 25 Nov	28d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
29 Oct - 4 Nov	6d	Wed - Tue	YUL-ORD	$239	Details >	$239 >
29 Oct - 13 Nov	15d	Wed - Thu	YUL-ORD	$239	Details >	$239 >
29 Oct - 18 Nov	20d	Wed - Tue	YUL-ORD	$239	Details >	$239 >
29 Oct - 19 Nov	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
31 Oct - 26 Nov	26d	Fri - Wed	YUL-ORD	$239	Details >	$239 >

1 Nov - 22 Nov	21d	Sat - Sat	YUL-MDW	$175	Details >	$175 >
4 Nov - 18 Nov	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
5 Nov - 19 Nov	14d	Wed - Wed	YUL-MDW	$176	Details >	$176 >
1 Nov - 27 Nov	26d	Sat - Thu	YUL-ORD	$239	Details >	$239 >
4 Nov - 6 Nov	2d	Tue - Thu	YUL-ORD	$239	Details >	$239 >
4 Nov - 8 Nov	4d	Tue - Sat	YUL-ORD	$239	Details >	$239 >
4 Nov - 23 Nov	19d	Tue - Sun	YUL-ORD	$239	Details >	$239 >
4 Nov - 25 Nov	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
5 Nov - 20 Nov	15d	Wed - Thu	YUL-ORD	$239	Details >	$239 >
5 Nov - 22 Nov	17d	Wed - Sat	YUL-ORD	$239	Details >	$239 >
5 Nov - 24 Nov	19d	Wed - Mon	YUL-ORD	$239	Details >	$239 >
5 Nov - 26 Nov	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
7 Nov - 1 Dec	24d	Fri - Mon	YUL-ORD	$239	Details >	$239 >
11 Nov - 13 Nov	2d	Tue - Thu	YUL-ORD	$239	Details >	$239 >
11 Nov - 23 Nov	12d	Tue - Sun	YUL-ORD	$239	Details >	$239 >
11 Nov - 2 Dec	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
12 Nov - 16 Nov	4d	Wed - Sun	YUL-ORD	$239	Details >	$239 >
12 Nov - 3 Dec	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
12 Nov - 6 Dec	24d	Wed - Sat	YUL-ORD	$239	Details >	$239 >
16 Nov - 9 Dec	23d	Sun - Tue	YUL-ORD	$239	Details >	$239 >
18 Nov - 22 Nov	4d	Tue - Sat	YUL-ORD	$239	Details >	$239 >
18 Nov - 27 Nov	9d	Tue - Thu	YUL-ORD	$239	Details >	$239 >
18 Nov - 28 Nov	10d	Tue - Fri	YUL-ORD	$239	Details >	$239 >
18 Nov - 30 Nov	12d	Tue - Sun	YUL-ORD	$239	Details >	$239 >
18 Nov - 1 Dec	13d	Tue - Mon	YUL-ORD	$239	Details >	$239 >
18 Nov - 3 Dec	15d	Tue - Wed	YUL-ORD	$239	Details >	$239 >
18 Nov - 4 Dec	16d	Tue - Thu	YUL-ORD	$239	Details >	$239 >
18 Nov - 8 Dec	20d	Tue - Mon	YUL-ORD	$239	Details >	$239 >
18 Nov - 9 Dec	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
19 Nov - 25 Nov	6d	Wed - Tue	YUL-ORD	$239	Details >	$239 >
19 Nov - 29 Nov	10d	Wed - Sat	YUL-ORD	$239	Details >	$239 >
19 Nov - 7 Dec	18d	Wed - Sun	YUL-ORD	$239	Details >	$239 >
19 Nov - 8 Dec	19d	Wed - Mon	YUL-ORD	$239	Details >	$239 >
19 Nov - 10 Dec	21d	Wed - Wed	YUL-ORD	$239	Details >	$239 >
19 Nov - 12 Dec	23d	Wed - Fri	YUL-ORD	$239	Details >	$239 >
19 Nov - 15 Dec	26d	Wed - Mon	YUL-ORD	$239	Details >	$239 >
24 Nov - 2 Dec	8d	Mon - Tue	YUL-ORD	$239	Details >	$239 >
25 Nov - 4 Dec	9d	Tue - Thu	YUL-ORD	$239	Details >	$239 >
25 Nov - 7 Dec	12d	Tue - Sun	YUL-ORD	$239	Details >	$239 >
25 Nov - 16 Dec	21d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
26 Nov - 8 Dec	12d	Wed - Mon	YUL-ORD	$239	Details >	$239 >
26 Nov - 16 Dec	20d	Wed - Tue	YUL-ORD	$239	Details >	$239 >

2 Dec - 16 Dec	14d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
9 Dec - 16 Dec	7d	Tue - Tue	YUL-ORD	$239	Details >	$239 >
9 Dec - 17 Dec	8d	Tue - Wed	YUL-ORD	$239	Details >	$239 >
10 Dec - 6 Jan	27d	Wed - Tue	YUL-ORD	$239	Details >	$239 >

6 Jan - 13 Jan	7d	Tue - Tue	YUL-MDW	$181	Details >	$181 >
6 Jan - 20 Jan	14d	Tue - Tue	YUL-MDW	$176	Details >	$176 >
10 Jan - 17 Jan	7d	Sat - Sat	YUL-MDW	$180	Details >	$180 >
12 Jan - 19 Jan	7d	Mon - Mon	YUL-MDW	$180	Details >	$180 >
13 Jan - 20 Jan	7d	Tue - Tue	YUL-MDW	$180	Details >	$180 >
13 Jan - 27 Jan	14d	Tue - Tue	YUL-MDW	$178	Details >	$178 >
14 Jan - 21 Jan	7d	Wed - Wed	YUL-MDW	$180	Details >	$180 >
20 Jan - 3 Feb	14d	Tue - Tue	YUL-MDW	$175	Details >	$175 >
21 Jan - 4 Feb	14d	Wed - Wed	YUL-MDW	$175	Details >	$175 >
27 Jan - 3 Feb	7d	Tue - Tue	YUL-MDW	$180	Details >	$180 >
27 Jan - 4 Feb	8d	Tue - Wed	YUL-MDW	$180	Details >	$180 >
27 Jan - 6 Feb	10d	Tue - Fri	YUL-MDW	$179	Details >	$179 >
27 Jan - 10 Feb	14d	Tue - Tue	YUL-MDW	$175	Details >	$175 >
28 Jan - 11 Feb	14d	Wed - Wed	YUL-MDW	$175	Details >	$175 >
30 Jan - 5 Feb	6d	Fri - Thu	YUL-MDW	$180	Details >	$180 >
30 Jan - 6 Feb	7d	Fri - Fri	YUL-MDW	$180	Details >	$180 >
30 Jan - 10 Feb	11d	Fri - Tue	YUL-MDW	$182	Details >	$182 >
30 Jan - 20 Feb	21d	Fri - Fri	YUL-MDW	$175	Details >	$175 >
30 Jan - 28 Feb	29d	Fri - Sat	YUL-MDW	$173	Details >	$173 >
31 Jan - 8 Feb	8d	Sat - Sun	YUL-MDW	$180	Details >	$180 >

1 Feb - 8 Feb	7d	Sun - Sun	YUL-MDW	$180	Details >	$180 >
2 Feb - 8 Feb	6d	Mon - Sun	YUL-MDW	$184	Details >	$184 >
2 Feb - 9 Feb	7d	Mon - Mon	YUL-MDW	$180	Details >	$180 >
3 Feb - 10 Feb	7d	Tue - Tue	YUL-MDW	$180	Details >	$180 >
4 Feb - 11 Feb	7d	Wed - Wed	YUL-MDW	$180	Details >	$180 >
10 Feb - 24 Feb	14d	Tue - Tue	YUL-MDW	$175	Details >	$175 >
11 Feb - 19 Feb	8d	Wed - Thu	YUL-MDW	$180	Details >	$180 >
11 Feb - 25 Feb	14d	Wed - Wed	YUL-MDW	$178	Details >	$178 >

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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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

End of the American requirement to remove shoes at airport security

Bomb threats in 6 Canadian airports: 2 reminders of basic things related to the situation

Best Canadian airlines ranking (2025)

Travel Rewards

Dates spotted: Direct transatlantic business class flights for 66,667 Amex points (not the best deal, but…)

34 best redemptions of Avios points (2025)

9 travel rewards updates (roundup post)

Follow Flytrippers on Facebook

Follow Flytrippers on Twitter