Airlines operating on route
Below you will find a list of airlines operating flights on the Calgary — Chicago route and the starting prices for flights of each specific airline on it.
Starting at $110
Starting at $150
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.
Below you will find a list of airlines operating flights on the Calgary — Chicago route and the starting prices for flights of each specific airline on it.
Starting at $110
Starting at $150
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.
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.
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
Unable to find information about the schedule of direct flights from
Calgary — Chicago
07/05/2025
Departure date
Direct flight
UA2048
Starting at $483
We couldn't find any special offers for flights from Calgary to Chicago
The cheapest one-way flight from Calgary to Chicago departs on 07/05/2025, is operated by American Airlines and costs $129
The cheapest roundtrip flight from Calgary to Chicago departs on 08/09/2025, is operated by Air Canada and costs $163
Fastest flight from Calgary to Chicago takes 16h 46m
There are no direct flights on this route.
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.
The cheapest flight ticket from Calgary to Chicago according to data for the last 48 hours costs $129
Often the best time to buy tickets from Calgary to Chicago is 2 months before departure.
The fastest flights from Calgary to Chicago start from 16 hours 46 minutes in the air.
The following airlines operate direct flights on the route Calgary — Chicago: United Airlines
