Unable to find information about the schedule of direct flights from
Compare airlines, prices, and flight durations for your trip
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Calgary to Chicago:
•
•
•
•
•
•
Answers to questions about the route that travelers are most interested in.
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
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.
Calgary — Chicago
05/27/2026
Departure
Direct flight
UA1968
starting at $117
Calgary — Chicago
09/19/2026
Departure
Direct flight
AA2389
starting at $406
Calgary — Chicago
04/23/2026
Departure
Direct flight
UA1655
starting at $298
The Calgary — Chicago route is served by multiple airlines, including United Airlines, American Airlines, and Air Canada. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $117, and depending on season and promotions, even better deals may appear. With our service, you can easily compare available options and book tickets that match your plans. The variety of carriers allows flexible choices and comfortable travel without overpaying.
The cheapest one-way flight from Calgary to Chicago departs on 05/27/2026, is operated by United Airlines and costs $117
The cheapest roundtrip flight from Calgary to Chicago departs on 05/07/2026, is operated by United Airlines and costs $292
Fastest flight from Calgary to Chicago takes 3h 37m
There are direct flights on this route 3 days a week: We, Th, and Sa
The distance between Calgary and Chicago is 2249km (1394 miles). There are 10 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 1:40 PM
The cheapest flight ticket from Calgary to Chicago according to data for the last 48 hours costs $117
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: July.
The fastest flights from Calgary to Chicago start from 3 hours 37 minutes in the air.
The following airlines operate direct flights on the route Calgary — Chicago: United Airlines, American Airlines
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 non-stop 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
