Cheap Flights from Calgary to Chicago Starting at $108

Helping travelers to find the best flight offers

Cheapest flights from Calgary to Chicago

Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Calgary to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.

Cheapest one way flight

$108

Air Canada
Air Canada
1 transfer
7h 57m
06/03/2025

The cheapest one-way flight from Calgary to Chicago departs on 06/03/2025, is operated by Air Canada and costs $108

Cheapest round trip flight

$350

Westjet
Westjet
2 transfers
16h 1m
06/26/2025

The cheapest roundtrip flight from Calgary to Chicago departs on 06/26/2025, is operated by Westjet and costs $350

The fastest flight

7h 57m

Fastest flight from Calgary to Chicago takes 7h 57m

Direct flights

No direct flights

There are no direct flights on this route.

Earliest flight

12:15 PM

Latest flight

1:18 PM

Direct flights count

48

Distance

2249km

Timezone difference

1h

The distance between Calgary and Chicago is 2249km (1394 miles). There are 48 direct flights from Calgary to Chicago. The time difference between Calgary and Chicago is 1h . Flights from Calgary begin at 12:15 PM. The latest flight from Calgary departs at 1:18 PM.

See also:

Cheap flights to United States

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Direct flights airfares to Chicago

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Cheapest air tickets to Calgary

Airfare from Calgary to Chicago by month

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Calgary to Chicago

  • Avg Price

Airlines operating on route

Westjet
Westjet

Starting at $102

Direct Flights from Calgary to Chicago

Chicago city image

Calgary — Chicago

YYC — CHI

06/03/2025

Departure date

Direct flight

Westjet

WS1588

Starting at $218

Schedule of direct flights from Calgary to Chicago

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Calgary to Chicago:

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Unable to find information about the schedule of direct flights from

Calgary airports overview

YYC
Calgary International Airport
United Airlines
Air Canada
Airlines flying to this airport
$108
Starting at
$108
on average

Chicago airports overview

ORD
O'Hare International Airport
United Airlines
Air Canada
Airlines flying to this airport
$108
Starting at
$108
on average

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

How much is the cheapest flight ticket from Calgary to Chicago?

The cheapest flight ticket from Calgary to Chicago according to data for the last 48 hours costs $108

When is the best time to buy air tickets on the route Calgary — Chicago?

Often the best time to buy tickets from Calgary to Chicago is 2 months before departure.

How long does it take to fly from Calgary to Chicago?

The fastest flights from Calgary to Chicago start from 7 hours 57 minutes in the air.

Which airline can fly direct from Calgary to Chicago?

The following airlines operate direct flights on the route Calgary — Chicago: Westjet

Special offers and sales on air tickets from Calgary to Chicago

We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.

Alternative routes

Bellingham ➜ Chicago•Spokane ➜ Chicago•Edmonton ➜ Chicago•Kamloops ➜ Chicago•Yakima ➜ Chicago•Kelowna ➜ Chicago•Red Deer ➜ Chicago•Saskatoon ➜ Chicago•Abbotsford ➜ Chicago•Calgary ➜ Appleton•Calgary ➜ Kalamazoo•Calgary ➜ Champaign•Calgary ➜ Fort Wayne•Calgary ➜ Indianapolis•Calgary ➜ Lansing•Calgary ➜ Milwaukee•Calgary ➜ Muskegon•Calgary ➜ South Bend