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Cheap Flights from Calgary to Chicago starting at S$ 151

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 Calgary 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 Calgary to Chicago

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

Westjet
From S$ 151
United Airlines
From S$ 177
Delta Air Lines
From S$ 177
Lynx Air
From S$ 179
Flair Airlines
From S$ 182
Alaska Airlines
From S$ 194
Air Canada
From S$ 198
American Airlines
From S$ 312
Porter Airlines
From S$ 341
ANA airlines

Find more flights and airlines

Alternative Routes from Calgary to Chicago

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

  • Cheapest
    Westjet
    YYC
    12:30
    3h 35m
    Direct
    ORD
    17:05
    Calgary International Airport - O'Hare International Airport
    Sun, Jun 2Westjet
    S$ 151
  • Lynx Air
    YYC
    07:15
    13h 29m
    1 transfer
    MDW
    21:44
    Calgary International Airport - Midway International Airport
    Tue, Apr 23Lynx Air
    S$ 181
  • Flair Airlines
    YYC
    08:00
    12h 3m
    1 transfer
    RFD
    21:03
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Apr 4Flair Airlines
    S$ 391
  • Flair Airlines
    YYC
    08:00
    12h 3m
    1 transfer
    RFD
    21:03
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Apr 4Flair Airlines
    S$ 391
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from Calgary (YYC) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Calgary 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 Calgary (YYC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 545.
  • How long is a flight from Calgary (YYC) to Chicago (CHI)?

    It takes about 4 hours 26 minutes to fly from Calgary (YYC) 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 Calgary to Chicago depart?

    The earliest flight departs from Calgary (YYC) at 07:30 and arrives in Chicago (ORD) at 11:54.
  • What are the most popular airlines that fly from Calgary (YYC) to Chicago (CHI)?

    Airlines with flights from Calgary (YYC) to Chicago (CHI): United Airlines, Air Canada and Emirates.
  • What's the most popular airline for direct flights from Calgary (YYC) to Chicago (CHI)?

    United Airlines operates 1 direct flights from Calgary (YYC) to Chicago (CHI).
  • How many airports in Chicago?

Find cheapest flight ticket from Calgary to Chicago

Cheapest direct flight price

S$ 150

Cheapest return ticket price

S$ 281

Cheapest month

January

Peak season for travel

April