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Cheap Flights from Montreal to Chicago starting at S$ 165

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

  • One way
  • Round-trip

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

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 lowest average weekly prices of the corresponding route on Trip.com.
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 S$ 165
United Airlines
From S$ 186
Lynx Air
From S$ 189
Delta Air Lines
From S$ 196
Air Transat
From S$ 201
Air Canada
From S$ 213
Flair Airlines
From S$ 231
Westjet
From S$ 236
American Airlines
From S$ 239
Sun Country Airlines
From S$ 266
ANA airlines

Find more flights and airlines

Alternative Routes from Montreal to Chicago

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

  • Cheapest
    Porter Airlines
    YUL
    07:00
    4h 7m
    1 transfer
    MDW
    10:07
    Montreal-Trudeau International Airport - Midway International Airport
    Tue, Apr 2Porter Airlines
    S$ 165
  • United Airlines
    YUL
    08:30
    2h 36m
    Direct
    ORD
    10:06
    Montreal-Trudeau International Airport - O'Hare International Airport
    Tue, Apr 23United Airlines
    S$ 186
  • United Airlines
    YUL
    08:30
    2h 36m
    Direct
    ORD
    10:06
    Montreal-Trudeau International Airport - O'Hare International Airport
    Tue, Apr 23United Airlines
    S$ 186
    Find More Flights

Frequently Asked Questions

  • When to buy 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 is a flight from Montreal (YMQ) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 549.
  • How long is a flight from Montreal (YMQ) to Chicago (CHI)?

    It takes about 2 hours 39 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 time does the earliest flight from Montreal to Chicago depart?

    The earliest flight departs from Montreal (YUL) at 06:05 and arrives in Chicago (ORD) at 08:15.
  • What time does the latest flight from Montreal to Chicago depart?

    The latest flight departs from Montreal (YUL) at 19:45 and arrives in Chicago (ORD) at 21:23.
  • What are the most popular airlines that fly from Montreal (YMQ) to Chicago (CHI)?

    Airlines with flights from Montreal (YMQ) to Chicago (CHI): Ana, United Airlines, Air Canada, Air New Zealand and Copa Airlines.
  • 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?

Find cheapest flight ticket from Montreal to Chicago

Cheapest direct flight price

S$ 164

Cheapest return ticket price

S$ 304

Cheapest month

December

Peak season for travel

September