Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Air Canada

The cheapest airline(s) flying from Calgary to Chicago is Air Canada.

  • Air Canada Air Canada
  • WestJet WestJet
  • Delta Air Lines Delta Air Lines
  • American Airlines American Airlines
  • United Airlines United Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month August

Travel Period: May 2024 - April 2025

The cheapest month(s) to fly from Calgary to Chicago is August.

  • May 2024
  • Jun 2024
  • Jul 2024
  • Aug 2024
  • Sep 2024
  • Oct 2024
  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Calgary to Chicago is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday
Cheapest Time 11pm

The cheapest time of the day to fly from Calgary to Chicago is in the evening.

Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm

Flight Schedules

Last Updated: Tue, 2 Apr, 2024

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  • Availability
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  • 08:30 - 12:49
    YYC - ORD
  • 08:30 (YYC)Calgary Airport
  • 12:49 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2048)Boeing 737 700
  • 3h 19m
  • Direct
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  • Boeing 737 700
  • 12:30 - 16:50
    YYC - ORD
  • 12:30 (YYC)Calgary Airport
  • 16:50 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1655)Boeing 737 700
  • 3h 20m
  • Direct
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  • Boeing 737 700
  • 13:55 - 00:10+ 1
    YYC - ORD
  • 13:55 (YYC)Calgary Airport
  • 00:10 (ORD)Chicago O'Hare International Airport + 1
  • United Airlines (UA 750)Airbus
  • 9h 15m
  • Direct
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  • Airbus
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What’s the fastest flight time from Calgary to Chicago?

The fastest flight time for direct flights from Calgary to Chicago is 3 hours 19 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from Calgary?

The flight distance between Calgary and Chicago is 2251km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 08:30. The last flight of the day departs at 08:30. See the full list of flight times on Wego.

How many airlines offer direct flights from Calgary to Chicago?

There are 1 airlines that offer direct flights from Calgary to Chicago. Find out the list of airlines on Wego.