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YUL - MDW

C$ 196 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 Chicago departing on 22/4. 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

KAYAK searches 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
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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.

Recent round-trip flight deals from Montreal to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Montreal to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
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6:50 a.m. - 12:00 p.m.YUL-MDW
6h 10m1 stop
5:35 p.m. - 10:32 p.m.MDW-YUL
3h 57m1 stop
C$ 303Porter Airlines
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Sat, 19 Apr - Sun, 20 Apr
11:45 a.m. - 4:40 p.m.YUL-MDW
5h 55m1 stop
9:15 a.m. - 4:00 p.m.MDW-YUL
5h 45m1 stop
C$ 321Porter Airlines
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Sun, 27 Apr - Sun, 4 May
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
5:35 p.m. - 10:32 p.m.MDW-YUL
3h 57m1 stop
C$ 322Porter Airlines
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Thu, 24 Apr - Sun, 27 Apr
6:50 a.m. - 12:00 p.m.YUL-MDW
6h 10m1 stop
5:35 p.m. - 10:32 p.m.MDW-YUL
3h 57m1 stop
C$ 323Porter Airlines
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Sat, 19 Apr - Sun, 20 Apr
6:10 a.m. - 2:22 p.m.YUL-MDW
9h 12m1 stop
6:04 a.m. - 4:52 p.m.MDW-YUL
9h 48m1 stop
C$ 384Delta
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Sun, 20 Apr - Tue, 29 Apr
12:50 p.m. - 6:20 p.m.YUL-MDW
6h 30m1 stop
9:20 a.m. - 4:00 p.m.MDW-YUL
5h 40m1 stop
C$ 396Delta
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Thu, 24 Apr - Sun, 27 Apr
6:45 p.m. - 9:13 p.m.YUL-MDW
27h 28m1 stop
9:20 a.m. - 12:43 a.m.MDW-YUL
14h 23m2 stops
C$ 469WestJet
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Fri, 23 May - Sun, 25 May
11:45 a.m. - 4:40 p.m.YUL-MDW
5h 55m1 stop
10:20 a.m. - 12:37 a.m.MDW-YUL
13h 17m2 stops
C$ 471
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Sun, 20 Apr - Mon, 28 Apr
2:50 p.m. - 9:14 p.m.YUL-MDW
7h 24m1 stop
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 472
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Sat, 17 May - Tue, 20 May
6:45 a.m. - 9:38 p.m.YUL-MDW
15h 53m2 stops
9:21 a.m. - 11:18 p.m.MDW-YUL
12h 57m1 stop
C$ 477WestJet
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Sat, 21 Jun - Tue, 24 Jun

KAYAK's insights & trends for Montreal to Chicago flights

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

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 round-trip 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 May, where tickets cost C$ 365 (return) on average. On the other hand, the most expensive months are October and March, where the average cost of round-trip tickets is C$ 617 and C$ 521 respectively.
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Good to know

Low season

April

High season

December

Cheapest flight

C$ 196
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly (4% more expensive on average)
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Chicago

Are your dates flexible? Find out the best times to travel from Montreal to Chicago 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 C$ 137 for a one-way ticket and C$ 212 for a round-trip.

  • 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 travellers 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.

  • 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 Chicago

 
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 Chicago? 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.
7.9
Porter AirlinesOverall score based on 277 reviews
6.9Entertainment
7.6Food
8.2Boarding
8.7Crew
8.1Comfort
Airline reviews

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

8.0 ExcellentLouise, Mar 2025YYZ - YOW
Read more Porter Airlines reviews

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Everything you need to know for your flight from Montreal to Chicago

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)

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