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Cheap flights from Chicago to Calgary

Chicago
CHI
Calgary
YYC

Flight deals from Chicago to Calgary

Below you can see the best deals on flights Chicago — Calgary 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 11 August, from $119.

Top 10 cheap flights from Chicago to Calgary

WS
$ 120

Chicago — Calgary

17:3020:25
19 Aug 2026
3 h 55 m
Direct flight
WS
$ 121

Chicago — Calgary

17:3020:25
11 Aug 2026
3 h 55 m
Direct flight
WS
$ 121

Chicago — Calgary

17:3020:25
18 Aug 2026
3 h 55 m
Direct flight
AC
$ 125

Chicago — Montreal

08:4011:59
19 Aug 2026
2 h 19 m
Direct flight
WS
$ 128

Chicago — Calgary

17:3020:25
19 Aug 2026
3 h 55 m
Direct flight
WS
$ 128

Chicago — Calgary

17:3020:25
18 Aug 2026
3 h 55 m
Direct flight
WS
$ 128

Chicago — Calgary

17:3020:25
11 Aug 2026
3 h 55 m
Direct flight
AC
$ 130

Chicago — Toronto

17:3520:20
17 Aug 2026
1 h 45 m
Direct flight
AC
$ 130

Chicago — Toronto

15:4518:30
18 Aug 2026
1 h 45 m
Direct flight
AC
$ 130

Chicago — Toronto

14:1517:01
18 Aug 2026
1 h 46 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Calgary flight

On this page, you can find and book flights from Chicago to Calgary. The distance between the cities is 2,255 km, and there are approximately 17 flights per week.

Flights on this route are operated by United Airlines, WestJet, and American Airlines. Ticket prices are dynamic, so use the low-price calendar to find the best deals. Before your trip, check out the information on how to get to Chicago airport and the most convenient ways to reach the city from Calgary airport.

Flight ticket prices by day: Chicago — Calgary

Below is a calendar of the lowest flight ticket prices for Chicago — Calgary by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $109 in b, and the most expensive are around $175 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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Prices by month

Chicago → Calgary, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$179lowMay$185lowSep$211medium
Feb$185lowJun$224highOct$185low
Mar$198mediumJul$243highNov$179low
Apr$179lowAug$236highDec$230high

Some values are estimated based on seasonality.

When to fly

The warmest month in Calgary is July, with temperatures reaching +24.6°C, while rainfall peaks in June. The coldest weather occurs in February, when the temperature can drop to -14.7°C.

The lowest flight prices are recorded in August — $75. The most expensive month to buy a ticket is June, with prices starting $171.

September is a great time to visit: the weather remains pleasant, and prices drop. We recommend avoiding February due to extreme cold, unless you are planning a ski trip.

Temperature · Calgary

Dry and wet days · Calgary

Wind speed and direction · Calgary

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

  • Book in advance: The optimal time to search for tickets on this route is 4–6 weeks before departure.
  • Compare direct WestJet flights with connecting options from American Airlines, which are sometimes cheaper — $109.
  • Use the price dynamic chart on this page to see how costs change depending on the day of the week.
  • Check United's baggage policies, as fares on short transborder flights may not include a checked bag.

Airlines

There are 4 airlines operating on this route, with United Airlines and WestJet being the primary carriers. Most direct flights are operated by these companies, ensuring a steady connection between the cities. You can check the exact departure times and choose the most suitable flight option in the detailed schedule below.

  • American AirlinesAA
    7x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → YYC7x/week
      Duration
      3h 46m
      Days
      MTWTFSS
  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → YYC5x/week
      Duration
      3h 52m
      Days
      MTWTFSS
  • WestJetWS
    5x/week
    WebsiteFleet: 15325M pax/year
    • Direct flight ORD → YYC5x/week
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight ORD → YYC1x/week

Cities and airports on the Chicago — Calgary route

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

Departure airports
Arrival airports

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Real Stories: How Quarantine is Going in Other Countries

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Frequently asked questions about the Chicago — Calgary flight

How long is the flight from Chicago to Calgary?

The approximate travel time for a direct flight is about 2 hours and 40 minutes, covering a distance of 2,255 km.

Which airlines fly this route?

Regular flights are operated by United Airlines (UA), WestJet (WS), American Airlines (AA), and British Airways (BA).

Are there direct flights from Chicago to Calgary?

Yes, direct flights on this route are typically operated by WestJet and United.

How much is the cheapest ticket?

Ticket prices change constantly; you can find the current lowest price in the low-price calendar on this page.

Which airport does the flight arrive at?

All flights from Chicago arrive at Calgary International Airport (YYC).

Where else you can fly from Chicago

See all

Where else you can fly from Calgary

See all

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