Unable to find information about the schedule of direct flights from
Helping travelers to find the best flight offers
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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights 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.
Unable to find information about the schedule of direct flights from
The cheapest one-way flight from Calgary to Chicago departs on 12/25/2025, is operated by Air Canada and costs $102
There is no information about the cheapest roundtrip flight from Calgary to Chicago
Fastest flight from Calgary to Chicago takes 3h 35m
There are direct flights on this route 1 day a week: Mo
The distance between Calgary and Chicago is 2249km (1394 miles). There are 22 direct flights from Calgary to Chicago. The time difference between Calgary and Chicago is 1h. Flights from Calgary begin at 9:00 AM. The latest flight from Calgary departs at 12:37 PM
Calgary — Chicago
12/07/2025
Departure
Direct flight
UA1655
Starting at $252
Calgary — Chicago
12/20/2025
Departure
Direct flight
UA1655
Starting at $577
Calgary — Chicago
12/21/2025
Departure
Direct flight
AA4161
Starting at $387
Calgary — Chicago
12/22/2025
Departure
Direct flight
WS1610
Starting at $186
Calgary — Chicago
12/24/2025
Departure
Direct flight
UA1655
Starting at $300
Calgary — Chicago
12/25/2025
Departure
Direct flight
AC4026
Starting at $394
Starting at $252
Starting at $169
Starting at $186
Starting at $102
Starting at $297
The route Calgary — Chicago is served by many carriers — 5 in total, including United Airlines, American Airlines, Westjet, Air Canada, and Flair Airlines Ltd.. This gives passengers wide opportunities: from finding the lowest fare (from $102) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
The cheapest flight ticket from Calgary to Chicago according to data for the last 48 hours costs $102
Often the best time to buy tickets from Calgary to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Calgary to Chicago can be found flying in these months: January.
The fastest flights from Calgary to Chicago start from 3 hours 35 minutes in the air.
The following airlines operate direct flights on the route Calgary — Chicago: United Airlines, American Airlines, Westjet
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
A direct flight is the most convenient and comfortable way to fly from Calgary to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
We couldn't find any special offers for flights from Calgary to Chicago
