starting at $398
starting at $134
starting at $119
starting at $180
Compare airlines, prices, and flight durations for your trip
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 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.
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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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.
The route Calgary — Chicago is served by many carriers — 4 in total, including American Airlines, Westjet, Air Canada, and Porter Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $119) 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.
starting at $398
starting at $134
starting at $119
starting at $180
Calgary — Chicago
02/02/2026
Departure
Direct flight
AA4161
starting at $408
Calgary — Chicago
04/11/2026
Departure
Direct flight
AA4161
starting at $398
Calgary — Chicago
07/17/2026
Departure
Direct flight
WS1610
starting at $217
Unable to find information about the schedule of direct flights from
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RFD
The cheapest one-way flight from Calgary to Chicago departs on 04/11/2026, is operated by Air Canada and costs $119
The cheapest roundtrip flight from Calgary to Chicago departs on 02/27/2026, is operated by Air Canada and costs $197
Fastest flight from Calgary to Chicago takes 3h 28m
There are direct flights on this route 3 days a week: Mo, Fr, and Sa
The distance between Calgary and Chicago is 2249km (1394 miles). The time difference between Calgary and Chicago is 1h
We couldn't find any special offers for flights from Calgary to Chicago
The cheapest flight ticket from Calgary to Chicago according to data for the last 48 hours costs $119
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: February.
The fastest flights from Calgary to Chicago start from 3 hours 28 minutes in the air.
The following airlines operate direct flights on the route Calgary — Chicago: 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