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Cheap flights from Montreal to Chicago from $165

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Montreal to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
3:20 pm - 9:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
4h 52m1 stop Toronto Island
$281Porter Airlines
Tue, Sep 22 - Wed, Sep 23
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$282Porter Airlines
Sat, Oct 3 - Sat, Oct 10
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$283Porter Airlines
Wed, Sep 23 - Sat, Sep 26
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$284Porter Airlines
Wed, Oct 14 - Mon, Oct 19
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$285Porter Airlines
Fri, Sep 25 - Sun, Sep 27
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$286Porter Airlines
Sat, Sep 26 - Sun, Sep 27
Porter Airlines Logo
6:30 am - 11:00 amYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 30m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$287Porter Airlines
Thu, Oct 22 - Sat, Oct 24
Porter Airlines Logo
10:35 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
5h 00m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$288Porter Airlines
Sun, Oct 11 - Sat, Oct 17
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$289Porter Airlines
Fri, Sep 25 - Sun, Sep 27
Porter Airlines Logo
9:00 am - 2:35 pmYUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
6h 35m1 stop Toronto Island
Porter Airlines Logo
11:45 am - 6:12 pmMDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
5h 27m1 stop Toronto Island
$291Porter Airlines
Thu, Sep 24 - Tue, Sep 29

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Delta flights from Montreal to Chicago Midway Airport

Our best Delta deals on Montreal to Chicago Midway Airport flight tickets
Delta
Oct 22
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
4h 32m
1 stop
MDW9:32 amChicago Midway
Oct 29
MDW6:44 pmChicago Midway
3h 41m
1 stop
YUL11:25 pmMontreal Pierre Elliott Trudeau Intl
$312
Delta
Oct 21
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
4h 32m
1 stop
MDW9:32 amChicago Midway
Oct 26
MDW1:27 pmChicago Midway
8h 58m
1 stop
YUL11:25 pmMontreal Pierre Elliott Trudeau Intl
$314
Delta
Nov 10
YUL6:00 amMontreal Pierre Elliott Trudeau Intl
7h 51m
1 stop
MDW12:51 pmChicago Midway
Nov 30
MDW6:44 pmChicago Midway
3h 43m
1 stop
YUL11:27 pmMontreal Pierre Elliott Trudeau Intl
$316

Porter Airlines flights from Montreal to Chicago Midway Airport

Our best Porter Airlines deals on Montreal to Chicago Midway Airport flight tickets
Porter Airlines
Oct 3
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 amChicago Midway
Oct 10
MDW11:45 amChicago Midway
5h 27m
1 stop
YUL6:12 pmMontreal Pierre Elliott Trudeau Intl
$281
Porter Airlines
Oct 3
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 amChicago Midway
Oct 10
MDW11:45 amChicago Midway
5h 27m
1 stop
YUL6:12 pmMontreal Pierre Elliott Trudeau Intl
$282
Porter Airlines
Sep 23
YUL6:30 amMontreal Pierre Elliott Trudeau Intl
5h 30m
1 stop
MDW11:00 amChicago Midway
Sep 26
MDW11:45 amChicago Midway
5h 27m
1 stop
YUL6:12 pmMontreal Pierre Elliott Trudeau Intl
$283

momondo Fare Finder

 
Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

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Price

Cheapest round-trip
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/22

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Wed 9/23

3:20 pm-9:12 pm

1 stop4h 52m

$281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 10/3

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sat 10/10

11:45 am-6:12 pm

1 stop5h 27m

$282

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/23

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sat 9/26

11:45 am-6:12 pm

1 stop5h 27m

$283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/14

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Mon 10/19

11:45 am-6:12 pm

1 stop5h 27m

$284

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/25

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Sun 9/27

11:45 am-6:12 pm

1 stop5h 27m

$285

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 9/26

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sun 9/27

11:45 am-6:12 pm

1 stop5h 27m

$286

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/22

6:30 am-11:00 am

1 stop5h 30m

Chicago Midway

Sat 10/24

11:45 am-6:12 pm

1 stop5h 27m

$287

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 10/11

10:35 am-2:35 pm

1 stop5h 00m

Chicago Midway

Sat 10/17

11:45 am-6:12 pm

1 stop5h 27m

$288

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/25

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Sun 9/27

11:45 am-6:12 pm

1 stop5h 27m

$289

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/24

9:00 am-2:35 pm

1 stop6h 35m

Chicago Midway

Tue 9/29

11:45 am-6:12 pm

1 stop5h 27m

$291

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Montreal to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Montreal, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Montreal during the month January is also very affordable. Most momondo users find prices during this month for around $0.

When to book flights from Montreal to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montreal to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montreal to Chicago Midway Airport (YMQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montreal to Chicago Midway Airport

Best Price Found

$165

Fastest flight time

4h 37m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Montreal in the past 72 hours is $165. The best round-trip flight deal from Montreal to Chicago Midway Airport found on momondo in the last 72 hours is $281.
The fastest flight from Montreal to Chicago Midway Airport takes 4h 37m
There are no direct flights from Montreal to Chicago Midway Airport. There are no popular flight routes from Montreal to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Montreal to Chicago Midway Airport

  • How far is Montreal to Chicago Midway by plane?

    There are 752.3 mi between Montreal and Chicago Midway. 4h 37m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Montreal to Chicago Midway Airport?

    Prices for flights from Montreal to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Montreal to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Montreal to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montreal to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montreal to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Montreal to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Montreal with this policy.

How can momondo help me find flights from Montreal to Chicago?

momondo helps you find the best flight between Montreal and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Montreal to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Montreal. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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