Cheap Flight Tickets from Calgary (YYC) to Chicago (ORD), Starting at $148

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

$540

AC Air Canada • 1 stop • 18h 25m

Jul 21 – Jul 21

The cheapest round trip flight from Calgary to Chicago (YYC-ORD-YYC) is currently $540

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Cheapest Direct Flight

$148

AA American Airlines • nonstop • 7h 25m

Jul 21

The cheapest nonstop flight from Calgary to Chicago (YYC-ORD) is currently $148

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Fastest Flight

5h 36m

The fastest nonstop flight from Calgary to Chicago (YYC-ORD) takes 5h 36m

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 21 - Jul 21, Economy
AC
Calgary → Chicago
18h 25m
- • 1 stop
UA
Calgary → Chicago
11h 50m
- • 1 stop
$540
Air Canada
Jul 21 - Jul 28, Economy
AC
Calgary → Chicago
5h 37m
8:30 AM - 1:07 PM • nonstop
AC
Calgary → Chicago
5h 52m
8:40 AM - 11:32 AM • nonstop
$560
Air Canada
Jul 20 - Jul 27, Economy
AS
Calgary → Chicago
26h 43m
7:00 PM - 12:03 PM • 1 stop
WS
Calgary → Chicago
5h 55m
5:30 PM - 8:25 PM • nonstop
$1045
Alaska Airlines
Jul 20 - Jul 27, Economy
WS
Calgary → Chicago
5h 40m
12:00 PM - 4:40 PM • nonstop
WS
Calgary → Chicago
22h 10m
6:30 AM - 7:00 PM • 2 stops
$1385
WestJet Airlines
Jul 21 - Jul 21, Economy
AC
Calgary → Chicago
16h 45m
6:00 AM - 1:15 PM • 1 stop
AC
Calgary → Chicago
5h 52m
3:50 PM - 11:00 PM • 1 stop
$1682
Air Canada
Jul 21 - Jul 21, Economy
WS
Calgary → Chicago
16h 45m
1:00 AM - 12:44 PM • 1 stop
AC
Calgary → Chicago
5h 52m
3:50 PM - 11:45 PM • 1 stop
$1980
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 1:00 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 AC : USD 540
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 1:5300 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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