We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Browse Airline Reviews
Before you book your next flight, see reviews from travelers around the world
Read Reviews

Low fares for Calgary (YYC) to Chicago (CHI) Low fares for Calgary to Chicago
Tue 06/27 - Mon 07/10
13 days, 0 stops max
$485
Sun 07/16 - Sun 07/30
14 days, 0 stops max
$375
Thu 08/24 - Mon 08/28
4 days, 0 stops max
$349
Wed 09/06 - Fri 09/08
2 days, 0 stops max
$326
Wed 10/11 - Wed 10/18
7 days, 0 stops max
$282
Wed 11/01 - Tue 11/07
6 days, 0 stops max
$284
Tue 07/18 - Mon 07/24
6 days, 0 stops max
$368
Thu 07/06 - Thu 07/13
7 days, 0 stops max
$422
Tue 07/25 - Thu 08/10
16 days, 0 stops max
$423
Thu 07/20 - Fri 07/28
8 days, 0 stops max
$423
Mon 07/17 - Tue 07/25
8 days, 0 stops max
$424
Wed 07/19 - Tue 07/25
6 days, 0 stops max
$440
About TripAdvisor Flights

Your one-stop shop for finding the best flights from Calgary to Chicago. Simply tell us where and when you want to travel and we'll do all the legwork for you. Featuring the most powerful shopping tools on the web, we search the largest online travel websites, established airfare discounters, plus the world's leading airlines and low-cost carriers to bring back thousands of flight options.

Travel information for Calgary, Canada to Chicago

Route information
  • Calgary, Canada is 1381 miles from Chicago
  • There are 7 daily flights from Calgary, Canada to Chicago
  • There are 18 weekly flights from Calgary, Canada to Chicago
  • 13 non-stop flights are operating from Calgary, Canada to Chicago today
  • Air Canada has the most nonstop flights between Calgary, Canada and Chicago
  • Toronto, Canada - Pearson International Airport is the most popular connection for one stop flights between Calgary, Canada and Chicago
In-Flight Information
  • The average flying time for a direct flight from Calgary, Canada to Chicago is 3 hours 34 minutes
  • Most direct flights leave around 6:00 MDT
Arrival information
  • Chicago is 16 mi from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 95 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 239 cities.
    • Every week, at least 26,600 domestic flights and 2,807 international flights depart from O'Hare Intl Airport.
  • Chicago is 9 mi from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 8 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 73 cities.
    • Every week, at least 2,807 domestic flights and 126 international flights depart from Midway Airport.

Shop for hotels in Chicago