Cheap Flight Tickets from Calgary (YYC) to Chicago (ORD), Starting at $458

Good to Know: Cheapest and Fastest YYC - ORD Flights

Useful information for finding best airline tickets from Calgary International to Chicago O'Hare International on your next trip.

Cheapest Round Trip Flight

$484

AC Air Canada • 1 stop • 13h 36m

Jul 15 – Jul 15

The cheapest round trip flight from Calgary to Chicago (YYC-ORD-YYC) is currently $484

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Cheapest One way Flight

$458

WS WestJet Airlines • 2 stops • 22h

Jul 25

The cheapest one way flight from Calgary to Chicago (YYC-ORD) is currently $458

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Cheapest Direct Flight

$544

AA American Airlines • nonstop • 5h 35m

Jul 15

The cheapest nonstop flight from Calgary to Chicago (YYC-ORD) is currently $544

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Fastest Flight

5h 35m

The fastest nonstop flight from Calgary to Chicago (YYC-ORD) takes 5h 35m

Top Airlines Flying from Calgary to Chicago

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

WestJet Airlines

WestJet Airlines

American Airlines, AA

American Airlines

Air Canada-AC

Air Canada

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Calgary (YYC) to Chicago (ORD)

Compare and book low fare round-trip air tickets from Calgary to Chicago. Ideal for travelers with confirmed return itineraries.

Jul 15 - Jul 15, Economy
AC
Calgary → Chicago
13h 36m
1:00 AM - 11:20 AM • 1 stop
AC
Calgary → Chicago
14h 5m
2:15 PM - 10:00 PM • 1 stop
$484
Air Canada
Jul 15 - Jul 15, Economy
AC
Calgary → Chicago
13h 36m
5:50 AM - 2:55 PM • 1 stop
WS
Calgary → Chicago
14h 5m
5:30 PM - 8:25 PM • nonstop
$531
Air Canada
Jul 15 - Jul 15, Economy
AC
Calgary → Chicago
13h 36m
12:55 AM - 4:57 PM • 1 stop
AC
Calgary → Chicago
14h 5m
7:45 PM - 10:37 PM • nonstop
$641
Air Canada
Jul 15 - Jul 15, Economy
WS
Calgary → Chicago
5h 40m
12:00 PM - 4:40 PM • nonstop
AS
Calgary → Chicago
29h 10m
8:20 PM - 1:10 PM • 1 stop
$647
WestJet Airlines
Jul 15 - Jul 15, Economy
AC
Calgary → Chicago
13h 36m
1:00 AM - 1:22 PM • 2 stops
AC
Calgary → Chicago
14h 5m
3:45 PM - 11:45 PM • 1 stop
$656
Air Canada
Jul 15 - Jul 15, Economy
WS
Calgary → Chicago
12h
6:45 AM - 3:05 PM • 1 stop
WS
Calgary → Chicago
5h 55m
5:30 PM - 8:25 PM • nonstop
$1169
WestJet Airlines

Fly from Calgary to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Calgary to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Calgary to Chicago Flights

What are the airports in Calgary?
YYC
What’s the most popular airline flying from YYC to ORD?
The most popular airline flying from Calgary to Chicago are
Can I fly from YYC to ORD non-stop?
Yes, you can fly YYC to ORD non-stop on
Which airlines fly nonstop between Calgary and Chicago?
The non-stop flights between Calgary and Chicago are .
What’s the earliest departure time from YYC to ORD Airport?
The earliest flight leaves YYC at 12:55 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
Can I make changes to my Calgary to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from YYC to ORD?
Read the fare rules of the Calgary to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Calgary and Chicago?
operate flights between Calgary and Chicago
How long does a flight from Calgary to Chicago take?
It takes approximately 3 hour to fly non-stop from YYC to ORD, which is 1385.16 miles by air.
Which airlines provide the cheapest flights from Calgary (YYC) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from YYC were found on WS : USD 458
Do I need a passport to fly between YYC and ORD?
Yes
What’s the latest departure time from YYC to ORD ?
The last flight leaves YYC at 6:30 pm

Calgary (YYC) to Chicago (ORD): Airport Information

Origin Airport Calgary International , Calgary, CA
Destination Airport Chicago O'Hare International , Chicago, US
Distance 1385 miles

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