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YUL - MDW

$135 Find cheap flights from Montreal to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montreal to Midway departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
sáb. 7/13
sáb. 7/20

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,216,777 times on KAYAK, and here is why:

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Cheap flight deals from Montreal to Midway (YUL-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montreal to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:50 pm - 4:17 pmYUL-MDW
4h 27m1 stop
8:00 am - 1:45 pmMDW-YUL
4h 45m1 stop
$221Porter Airlines
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vie., jul. 12 - mar., jul. 16
8:35 am - 11:32 amYUL-MDW
3h 57m1 stop
11:30 am - 6:00 pmMDW-YUL
5h 30m1 stop
$225Porter Airlines
Find Deal
sáb., jul. 27 - lun., jul. 29
4:10 pm - 9:37 pmYUL-MDW
6h 27m1 stop
11:05 am - 6:00 pmMDW-YUL
5h 55m1 stop
$248Air Transat
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lun., jul. 1 - mié., jul. 3
12:45 pm - 4:17 pmYUL-MDW
4h 32m1 stop
5:15 pm - 10:55 pmMDW-YUL
4h 40m1 stop
$274Air Transat
Find Deal
dom., jul. 7 - jue., jul. 11
12:45 pm - 4:17 pmYUL-MDW
4h 32m1 stop
8:40 am - 2:00 pmMDW-YUL
4h 20m1 stop
$281
Find Deal
dom., jul. 7 - dom., jul. 14
3:10 pm - 7:02 pmYUL-MDW
4h 52m1 stop
12:15 pm - 5:55 pmMDW-YUL
4h 40m1 stop
$296
Find Deal
sáb., ago. 10 - dom., ago. 18
7:00 am - 5:04 pmYUL-MDW
11h 04m2 stops
3:48 pm - 11:59 pmMDW-YUL
7h 11m1 stop
$337Delta
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sáb., sep. 14 - mar., sep. 17
7:30 am - 6:31 pmYUL-MDW
12h 01m1 stop
7:11 pm - 1:20 pmMDW-YUL
17h 09m2 stops
$353WestJet
Find Deal
mar., jul. 2 - vie., jul. 5
9:15 pm - 11:57 amYUL-MDW
15h 42m2 stops
10:38 am - 5:25 pmMDW-YUL
5h 47m1 stop
$382WestJet
Find Deal
lun., sep. 23 - vie., sep. 27
7:00 am - 5:05 pmYUL-MDW
11h 05m2 stops
2:24 pm - 11:12 pmMDW-YUL
7h 48m1 stop
$418Delta
Find Deal
mié., jul. 3 - dom., jul. 7

Flights from Montreal to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Montreal to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Montreal to Chicago Midway Airport?

The average price of all flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Montreal to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to Montreal, the best deals are generally found on Tuesday, with Monday being the most expensive.

What is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is July, where tickets cost $250 on average. On the other hand, the most expensive months are September and August, where the average cost of tickets is $455 and $355 respectively.

Which airlines provide the cheapest flights from Montreal to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Porter Airlines ($135) and Air Transat ($162). The cheapest round-trip tickets were found on Porter Airlines ($221) and Air Transat ($248).

Good to know

Low season

April

High season

June

Cheapest flight

$135
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Midway

Are your dates flexible? Find out the best times to travel from Montreal to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Montreal to Chicago Midway Airport flights

  • What is the cheapest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport was $135 for a one-way ticket and $221 for a round-trip.

  • Do I need a passport to fly between Montreal and Chicago Midway Airport?

    A passport is required to fly from Montreal to Chicago Midway Airport.

  • Which aircraft models fly most regularly from Montreal to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Montreal to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Montreal and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Montreal to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montreal to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montreal to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Montreal is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montreal to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Montreal with another airline. Booking your flights between Montreal and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montreal to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Montreal up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Montreal to Midway

 
See real verified KAYAK customer reviews for airlines flying from Montreal to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montreal to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Porter AirlinesOverall score based on 375 reviews
7.5Comfort
7.6Boarding
8.2Crew
6.6Entertainment
7.4Food
Airline reviews

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

6.0 GoodAnonymous, Jun 2024YOW - BOS
Read more about Porter Airlines reviews

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

Book cheap flights from Montreal to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Montreal to Chicago found on KAYAK in the last 72 hours.
7/12vie.
1 stopPorter Airlines
4h 07mYUL-MDW
$135
9/11mié.
1 stopPorter Airlines
4h 27mYUL-MDW
$141
8/26lun.
1 stopAir Transat
6h 17mYUL-MDW
$162
7/7dom.
1 stopAir Transat
4h 32mYUL-MDW
$164
9/10mar.
2 stopsWestJet
25h 23mYUL-MDW
$231
10/7lun.
2 stopsWestJet
15h 43mYUL-MDW
$234
7/6sáb.
2 stops
12h 16mYUL-MDW
$238
7/20sáb.
2 stops
12h 16mYUL-MDW
$252
7/3mié.
2 stopsDelta
11h 05mYUL-MDW
$329
7/12vie.
2 stopsDelta
10h 53mYUL-MDW
$348

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Last minute flights from Montreal to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Montreal to Chicago that are departing in the next 10 days.
6/18mar.
multi-stopPorter Airlines
4h 07mYUL-MDW
6/20jue.
multi-stopPorter Airlines
4h 45mMDW-YUL
$416
6/18mar.
multi-stopPorter Airlines
4h 27mYUL-MDW
6/19mié.
multi-stopPorter Airlines
3h 55mMDW-YUL
$442
6/15sáb.
multi-stopPorter Airlines
3h 57mYUL-MDW
6/17lun.
multi-stopPorter Airlines
4h 45mMDW-YUL
$497
6/15sáb.
multi-stopPorter Airlines
3h 57mYUL-MDW
6/17lun.
multi-stopPorter Airlines
6h 50mMDW-YUL
$499
6/15sáb.
multi-stop
17h 13mYUL-MDW
6/17lun.
multi-stop
12h 23mMDW-YUL
$516
6/18mar.
multi-stopWestJet
28h 51mYUL-MDW
6/20jue.
multi-stopWestJet
12h 41mMDW-YUL
$525
6/18mar.
multi-stopWestJet
28h 51mYUL-MDW
6/20jue.
multi-stopWestJet
21h 56mMDW-YUL
$554
6/18mar.
multi-stop
23h 57mYUL-MDW
6/20jue.
multi-stop
15h 43mMDW-YUL
$898

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Montreal - Chicago Midway Airport Flights

Departure:

Montreal (YUL)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Montreal

Cabin classes:

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