Cheap Flights From Calgary Intl. (YYC) To O'Hare Intl. (ORD)

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Cheapest Flights from Calgary (YYC) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $238 round trip and CA $151 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Mar 6 - Mon, Mar 9
YYC
Calgary
ORD
Chicago
CA $238 Roundtrip, just found
CA $238
Roundtrip
just found
Select WestJet flight, departing Fri, Mar 6 from Calgary to Chicago, returning Mon, Mar 9, priced at CA $238 just found
Mon, Nov 3 - Mon, Nov 10
YYC
Calgary
ORD
Chicago
CA $246 Roundtrip, found 6 days ago
CA $246
Roundtrip
found 6 days ago
Select WestJet flight, departing Mon, Nov 3 from Calgary to Chicago, returning Mon, Nov 10, priced at CA $246 found 6 days ago
Mon, Mar 30 - Fri, Apr 3
YYC
Calgary
ORD
Chicago
CA $249 Roundtrip, found 3 days ago
CA $249
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Mar 30 from Calgary to Chicago, returning Fri, Apr 3, priced at CA $249 found 3 days ago
Mon, Nov 17 - Fri, Nov 21
YYC
Calgary
ORD
Chicago
CA $250 Roundtrip, found 1 day ago
CA $250
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Nov 17 from Calgary to Chicago, returning Fri, Nov 21, priced at CA $250 found 1 day ago
Fri, Oct 17 - Thu, Oct 23
YYC
Calgary
ORD
Chicago
CA $251 Roundtrip, found 5 days ago
CA $251
Roundtrip
found 5 days ago
Select WestJet flight, departing Fri, Oct 17 from Calgary to Chicago, returning Thu, Oct 23, priced at CA $251 found 5 days ago
Thu, Oct 23 - Sun, Oct 26
YYC
Calgary
ORD
Chicago
CA $255 Roundtrip, found 14 hours ago
CA $255
Roundtrip
found 14 hours ago
Select WestJet flight, departing Thu, Oct 23 from Calgary to Chicago, returning Sun, Oct 26, priced at CA $255 found 14 hours ago
Fri, Oct 24 - Sun, Oct 26
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 23 hours ago
CA $256
Roundtrip
found 23 hours ago
Select WestJet flight, departing Fri, Oct 24 from Calgary to Chicago, returning Sun, Oct 26, priced at CA $256 found 23 hours ago
Fri, Dec 5 - Mon, Dec 8
YYC
Calgary
ORD
Chicago
CA $260 Roundtrip, found 1 day ago
CA $260
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Dec 5 from Calgary to Chicago, returning Mon, Dec 8, priced at CA $260 found 1 day ago
Sun, Oct 12 - Fri, Oct 17
YYC
Calgary
ORD
Chicago
CA $268 Roundtrip, found 2 hours ago
CA $268
Roundtrip
found 2 hours ago
Select WestJet flight, departing Sun, Oct 12 from Calgary to Chicago, returning Fri, Oct 17, priced at CA $268 found 2 hours ago
Fri, Nov 28 - Mon, Dec 1
YYC
Calgary
ORD
Chicago
CA $278 Roundtrip, found 4 days ago
CA $278
Roundtrip
found 4 days ago
Select WestJet flight, departing Fri, Nov 28 from Calgary to Chicago, returning Mon, Dec 1, priced at CA $278 found 4 days ago

Frequently asked questions

Are there direct flights from YYC to O'Hare Intl. Airport (ORD)?
If you'd like to travel as fast as possible from YYC Calgary International Airport to ORD, look up Air Canada, Delta and United Airlines. No airlines provide nonstop flights between the two locations, so you'll need to make at least one stopover.
What airlines fly from YYC to O'Hare Intl. Airport (ORD)?
With no direct flights available, it will be in your best interest to plan well in advance when you're traveling between Calgary Intl. Airport (YYC) and ORD. Find a convenient route with the least amount of connections and save yourself some time.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Calgary (YYC)

Travelers at YYC love to visit these top cities. Roam to the top destinations from Calgary (YYC) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago(ORD) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.