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Flights Calgary — Chicago

Calgary
YYC
Chicago
CHI

Cheap flights Calgary — Chicago

Below you can see the best deals on flights Calgary — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 19 August, from AED 594.

Top 10 cheap flights Calgary — Chicago

Direct flights Calgary — Chicago

Direct flight options for Calgary — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by American Airlines — travel time is 3 h 35 min.

Top 10 direct flights Calgary — Chicago

About the Calgary — Chicago flight

On this page, you can find and buy flight tickets for the Calgary — Chicago route. The direct distance between the cities is 2,255 km, and with up to 21 flights per week, you have plenty of flexibility when choosing your departure time. To plan your transfer, check out the information on how to get to the airport in Calgary and how to get from the airport to downtown Chicago.

Flights are operated by airlines such as United Airlines, WestJet, and American Airlines. Ticket prices are dynamic and depend on the departure date, so we recommend using the low-price calendar and the price trend chart on this page to find the best deals.

Flight schedule Calgary — Chicago

The table shows direct flights Calgary → Chicago on the selected date. The flight takes approximately 3 h 35 min. Regular flights are operated by American Airlines, United Airlines, WestJet and British Airways. Departures from Calgary International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: Calgary — Chicago

Below is a calendar of the lowest flight ticket prices for Calgary — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 548 in F, and the most expensive are around AED 612 in y. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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When to fly

The warmest month in Chicago is July, with average temperatures reaching 26.5°C. The lowest temperatures are recorded in January, when they drop to -5°C, while May is considered the rainiest period.

The most affordable flight prices are found in September, with tickets starting AED 548. Prices peak in July, when the minimum fare starts AED 612.

The best time to travel is September or November: during these months, prices stabilize and weather conditions remain comfortable. The period from May to June is characterized by higher rainfall, which is worth considering when planning.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Calgary — Chicago ticket

  • Book in advance: the best fares for flights from Calgary are usually available 1.5–2 months before your planned departure.
  • Compare baggage policies: United and American Airlines often restrict carry-on bags in their basic fares, so be sure to check the rules beforehand.
  • Use the low-price calendar: shifting your departure date by 1–2 days can reduce the ticket cost by AED 118 or more.
  • Choose direct flights: with around 21 flights per week, direct connections save time, while connecting flights might start AED 447 but significantly increase travel duration.

Airlines

Flights on the Calgary — Chicago route are served by 4 airlines, with United Airlines and WestJet being the primary carriers. Approximately 21 flights are operated weekly, including both direct options and connecting routes. Review the detailed schedule and fare conditions in the list below to find the best flight option for you.

  • American Airlines
    American AirlinesAA
    8x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight YYC → ORD8x/week
      Duration
      3h 40m
      Days
      MTWTFSS
    37.5%Open →
  • United Airlines
    United AirlinesUA
    8x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight YYC → ORD8x/week
      Duration
      3h 39m
      Days
      MTWTFSS
    37.5%Open →
  • WestJet
    WestJetWS
    5x/week
    WebsiteFleet: 15325M pax/year
    • Direct flight YYC → ORD5x/week
      Duration
      3h 40m
      Days
      MTWTFSS
    21.9%Open →
  • British Airways
    British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight YYC → ORD1x/week
    3.1%Open →

Cities and airports on the Calgary — Chicago route

Flights Calgary — Chicago depart from Calgary International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Calgary

YYC
Canada
About the cityHow to get thereWeatherAll about the country Canada
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Calgary — Chicago flight

How long is the flight from Calgary to Chicago?

With a distance of 2,255 km, a direct flight takes approximately 2 hours 45 minutes to 3 hours. Travel time may increase if you choose a connecting flight.

Which airlines fly this route?

Regular flights are operated by United Airlines, WestJet, American Airlines, and British Airways. There are about 21 flights per week on this route.

Are there direct flights?

Yes, direct flights are available for this destination. You can check the availability and schedule for specific dates using the search on this page.

Which airport do flights arrive at?

Flights from Calgary arrive at Chicago's main airports, most commonly O'Hare International Airport (ORD).

When is the best time to buy flight tickets?

It is recommended to book tickets at least 6–8 weeks before your trip. You can always track current price offers using the price trend chart.

Where else you can fly from Calgary

VancouverTorontoEdmontonKelownaSaskatoonWinnipegMontrealSeattleOttawaReginaNanaimoVictoriaGrande PrairieSan FranciscoNew York CityFrankfurt am MainAtlantaLondonCancunNashvilleBostonAmsterdamDetroitTokyoDublinAustinBarcelonaAnchorageCozumel

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester
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