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Flights from Montreal to Chicago
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Find Montreal to Chicago flights starting at CAD 185.

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        YUL12:30
        2h 55m
        Nonstop
        ORD14:25
        Mon, Nov 25|Montreal - Chicago|American Airlines
        CAD 185CAD 492
        62% OFF
        62% OFF
        CAD 492CAD 185

        Choose American Airlines flights from Montreal to Chicago. The one-way direct flight with American Airlines departs from Montreal-Trudeau International Airport on Mon, Nov 25, arriving at O'Hare International Airport. One-way Prices start from CAD 185 including taxes and charges.

      • YUL12:30
        2h 55m
        Nonstop
        ORD14:25
        Wed, Dec 4|Montreal - Chicago|American Airlines
        CAD 185CAD 492
        62% OFF
        62% OFF
        CAD 492CAD 185

        Choose American Airlines flights from Montreal to Chicago. The one-way direct flight with American Airlines departs from Montreal-Trudeau International Airport on Wed, Dec 4, arriving at O'Hare International Airport. One-way Prices start from CAD 185 including taxes and charges.

      • YUL12:30
        2h 55m
        Nonstop
        ORD14:25
        Sun, Nov 24|Montreal - Chicago|American Airlines
        CAD 187CAD 492
        62% OFF
        62% OFF
        CAD 492CAD 187

        Choose American Airlines flights from Montreal to Chicago. The one-way direct flight with American Airlines departs from Montreal-Trudeau International Airport on Sun, Nov 24, arriving at O'Hare International Airport. One-way Prices start from CAD 187 including taxes and charges.

      • YUL06:00
        2h 56m
        Nonstop
        ORD07:56
        Wed, Nov 27|Montreal - Chicago|United Airlines
        CAD 200
        CAD 200

        Choose United Airlines flights from Montreal to Chicago. The one-way direct flight with United Airlines departs from Montreal-Trudeau International Airport on Wed, Nov 27, arriving at O'Hare International Airport. One-way Prices start from CAD 200 including taxes and charges.

      • YUL06:00
        2h 56m
        Nonstop
        ORD07:56
        Tue, Nov 26|Montreal - Chicago|United Airlines
        CAD 398
        CAD 398

        Choose United Airlines flights from Montreal to Chicago. The one-way direct flight with United Airlines departs from Montreal-Trudeau International Airport on Tue, Nov 26, arriving at O'Hare International Airport. One-way Prices start from CAD 398 including taxes and charges.

      • YUL06:50
        4h 30m
        1 stop
        MDW10:20
        Sun, Nov 24|Montreal - Chicago|Porter Airlines
        CAD 181
        CAD 181

        Choose Porter Airlines flights from Montreal to Chicago. The one-way connecting flight with Porter Airlines departs from Montreal-Trudeau International Airport on Sun, Nov 24, arriving at Midway International Airport. One-way Prices start from CAD 181 including taxes and charges.

      • YUL06:50
        4h 30m
        1 stop
        MDW10:20
        Mon, Nov 25|Montreal - Chicago|Porter Airlines
        CAD 193
        CAD 193

        Choose Porter Airlines flights from Montreal to Chicago. The one-way connecting flight with Porter Airlines departs from Montreal-Trudeau International Airport on Mon, Nov 25, arriving at Midway International Airport. One-way Prices start from CAD 193 including taxes and charges.

      • YUL06:50
        4h 30m
        1 stop
        MDW10:20
        Fri, Nov 22|Montreal - Chicago|Porter Airlines
        CAD 194
        CAD 194

        Choose Porter Airlines flights from Montreal to Chicago. The one-way connecting flight with Porter Airlines departs from Montreal-Trudeau International Airport on Fri, Nov 22, arriving at Midway International Airport. One-way Prices start from CAD 194 including taxes and charges.

      • YUL18:30
        5h 50m
        1 stop
        ORD23:20
        Thu, Dec 12|Montreal - Chicago|United Airlines
        CAD 195
        CAD 195

        Choose United Airlines flights from Montreal to Chicago. The one-way connecting flight with United Airlines departs from Montreal-Trudeau International Airport on Thu, Dec 12, arriving at O'Hare International Airport. One-way Prices start from CAD 195 including taxes and charges.

      • YUL06:50
        4h 30m
        1 stop
        MDW10:20
        Fri, Nov 29|Montreal - Chicago|Porter Airlines
        CAD 196
        CAD 196

        Choose Porter Airlines flights from Montreal to Chicago. The one-way connecting flight with Porter Airlines departs from Montreal-Trudeau International Airport on Fri, Nov 29, arriving at Midway International Airport. One-way Prices start from CAD 196 including taxes and charges.

      • YMQ13:00
        3h 5m
        Nonstop
        CHI14:00
        Wed, Nov 27|Montreal - Chicago|American Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Montreal to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Montreal to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Porter Airlines
From CAD 181
American Airlines
From CAD 185
United Airlines
From CAD 195
Delta Air Lines
From CAD 201
WestJet
From CAD 215
Air Transat
From CAD 277
Air Canada
From CAD 392

Find more flights and airlines

Alternative Routes for Montreal to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Montreal to Chicago.

  • Cheapest
    Porter Airlines
    YUL
    06:50
    4h 30m
    1 transfer
    MDW
    10:20
    Montreal-Trudeau International Airport - Midway International Airport
    Sun, Nov 24Porter Airlines
    CAD 181
  • American Airlines
    YUL
    12:30
    2h 55m
    Nonstop
    ORD
    14:25
    Montreal-Trudeau International Airport - O'Hare International Airport
    Mon, Nov 25American Airlines
    CAD 185
  • American Airlines
    YUL
    12:30
    2h 55m
    Nonstop
    ORD
    14:25
    Montreal-Trudeau International Airport - O'Hare International Airport
    Mon, Nov 25American Airlines
    CAD 185
    Find More Flights

FAQ

  • When are flight tickets from Montreal (YMQ) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Montreal to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Montreal (YMQ) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 465.

  • How long is the flight from Montreal (YMQ) to Chicago (CHI)?

    It takes about 2 hours 48 minutes to fly from Montreal (YMQ) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Montreal (YMQ) to Chicago (CHI)?

    Airlines with flights from Montreal (YMQ) to Chicago (CHI): Qatar Airways, Air Canada, United Airlines, Iberia, American Airlines, avianca, Copa Airlines, Qantas Airways and Air New Zealand.

  • What's the most popular airline for direct flights from Montreal (YMQ) to Chicago (CHI)?

    United Airlines operates 1 direct flights from Montreal (YMQ) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Montreal to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Montreal to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information for Montreal to Chicago Flights

Cheapest direct flight priceCAD 181
Cheapest return ticket priceCAD 326
Off-season travel monthOctober
Peak season for travelAugust
Flight distance1,199.75km
Average flight time2 hours 48 minutes
Popular airlineAmerican Airlines

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