Cheap Flights from Calgary, AB to Chicago, IL from $59

Return flight: Chicago – Calgary

On Cheapflightsplus.com you will find 4 direct and 200 connecting flights from Calgary to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $170, book and save on cheap plane tickets and last minute offers. Also check out YYC-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Calgary to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $59 (one-way), $101 (round-trip).
Direct flights
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Full flight schedule will help you in detecting at what time planes fly from Calgary to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
08:30 — 12:49
08:30 — 12:49 AC5240 Air Canada
Calgary — Chicago
3h 19m
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from$185
12:30 — 16:50
12:30 — 16:50 AC4026 Air Canada
Calgary — Chicago
3h 20m
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from$185
15:15 — 19:40
15:15 — 19:40 AC4028 Air Canada
Calgary — Chicago
3h 25m
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from$185
00:50 — 14:58
00:50 — 06:31 AC158 Air Canada
Calgary — Toronto
7h 39m stop
14:10 — 14:58 AC509 Air Canada
Toronto — Chicago
13h 8m
including layover
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from$194
07:00 — 14:58
07:00 — 12:45 AC134 Air Canada
Calgary — Toronto
1h 25m stop
14:10 — 14:58 AC509 Air Canada
Toronto — Chicago
6h 58m
including layover
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from$174
09:55 — 18:42
09:55 — 15:31 AC138 Air Canada
Calgary — Toronto
2h 14m stop
17:45 — 18:42 AC4408 Air Canada
Toronto — Chicago
7h 47m
including layover
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from$207
10:15 — 20:00
10:15 — 16:02 AC394 Air Canada
Calgary — Ottawa
2h 29m stop
18:31 — 20:00 AC3553 Air Canada
Ottawa — Chicago
8h 45m
including layover
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from$170
11:00 — 19:20
11:00 — 16:53 AC318 Air Canada
Calgary — Montreal
1h 2m stop
17:55 — 19:20 AC7597 Air Canada
Montreal — Chicago
7h 20m
including layover
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from$170
12:35 — 21:32
12:35 — 17:09 AA3695 American Airlines
Calgary — Dallas
1h 51m stop
19:00 — 21:32 AA2585 American Airlines
Dallas — Chicago
7h 57m
including layover
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from$204
13:15 — 21:43
13:15 — 18:55 AC146 Air Canada
Calgary — Toronto
2h stop
20:55 — 21:43 AC515 Air Canada
Toronto — Chicago
7h 28m
including layover
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from$174
15:55 — 21:59
15:55 — 19:31 WS6354 WestJet
Calgary — Minneapolis
49m stop
20:20 — 21:59 WS7849 WestJet
Minneapolis — Chicago
5h 4m
including layover
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from$202
06:30 — 08:57
+1 day
06:30 — 12:28 AC316 Air Canada
Calgary — Montreal
1h 17m stop
13:45 — 15:08 AC7624 Air Canada
Montreal — Boston
15h 52m stop
07:00 — 08:57 NK2855 Spirit Airlines
Boston — Chicago
25h 27m
including layover
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from$214
17:15 — 18:20
+1 day
17:15 — 22:54 AC152 Air Canada
Calgary — Toronto
15h 6m stop
14:00 — 15:14 AC414 Air Canada
Toronto — Montreal
1h 16m stop
16:30 — 18:20 AC3078 Air Canada
Montreal — Chicago
24h 5m
including layover
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from$224
*Departure and arrival times - local. Updated on June 7, 2023

Flight Information

Below we will explain in detail what the flights cost on the destination from Calgary to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Calgary and Chicago is 2249 miles. Time difference between the cities is 1h. Airplanes depart 00:05 to 21:30 from 1 Calgary airport and arrive 00:05 to 21:30 to 7 Chicago airports. Average flight time is 3h 23m.

  • The fastest flight 3h 19m
  • Average flight time 3h 23m
  • The earliest flight 00:05
  • The latest flight 21:30
  • Distance 1398 ml

What is the lowest airfare Calgary to Chicago?

The cheapest plane ticket found by our users is $170. This airfare is for economy class on one-way AC318 flight by Air Canada for July 18, 2020 which leaves Calgary Int. in Calgary at 11:00 am and arrives at Chicago O'Hare International at 21:26.

Economy class
$170
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Business class
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First class
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Popular Airlines on the Route

The flight Calgary — Chicago is served by 6 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 7 departures per week at the price of from $ 204 . And the most expensive tickets are offered by Air Canada airline - from $ 2157.

Direct flights

There are 4 nonstop flights on the route. The fastest direct flight is AC5240 by Air Canada takes 3h 19m and the cheapest is AC318 by Air Canada for $185.

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Connecting Flights

There are 200 flights with layovers on the route. The fastest connecting flight is WS6354 by WestJet takes 5h 4m and the cheapest is AC318 by Air Canada for $170.

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Airports

You can fly from Calgary to Chicago from 1 airports (Calgary Int.).

Calgary airports

  • Calgary Int.-YYC
    from $170
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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