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 $288 round trip and CA $176 one way. Prices and availability subject to change. Additional terms may apply.

Wed., Sep. 3 - Sat., Oct. 18
YYC
Calgary
ORD
Chicago
CA $288 Roundtrip, found 5 hours ago
CA $288
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Wed., Sep. 3 from Calgary to Chicago, returning Sat., Oct. 18, priced at CA $288 found 5 hours ago
Mon., Sep. 8 - Thu., Sep. 18
YYC
Calgary
ORD
Chicago
CA $288 Roundtrip, found 5 hours ago
CA $288
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon., Sep. 8 from Calgary to Chicago, returning Thu., Sep. 18, priced at CA $288 found 5 hours ago
Wed., Sep. 3 - Thu., Sep. 18
YYC
Calgary
ORD
Chicago
CA $295 Roundtrip, found 5 hours ago
CA $295
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed., Sep. 3 from Calgary to Chicago, returning Thu., Sep. 18, priced at CA $295 found 5 hours ago
Sat., Sep. 6 - Sat., Sep. 20
YYC
Calgary
ORD
Chicago
CA $295 Roundtrip, just found
CA $295
Roundtrip
just found
Select United flight, departing Sat., Sep. 6 from Calgary to Chicago, returning Sat., Sep. 20, priced at CA $295 just found
Sat., Sep. 6 - Sat., Sep. 20
YYC
Calgary
ORD
Chicago
CA $297 Roundtrip, just found
CA $297
Roundtrip
just found
Select Air Canada flight, departing Sat., Sep. 6 from Calgary to Chicago, returning Sat., Sep. 20, priced at CA $297 just found
Tue., Sep. 2 - Tue., Sep. 9
YYC
Calgary
ORD
Chicago
CA $299 Roundtrip, found 5 hours ago
CA $299
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Tue., Sep. 2 from Calgary to Chicago, returning Tue., Sep. 9, priced at CA $299 found 5 hours ago
Sat., Sep. 6 - Sat., Sep. 20
YYC
Calgary
ORD
Chicago
CA $306 Roundtrip, just found
CA $306
Roundtrip
just found
Select Air Canada flight, departing Sat., Sep. 6 from Calgary to Chicago, returning Sat., Sep. 20, priced at CA $306 just found
Wed., Sep. 3 - Wed., Sep. 10
YYC
Calgary
ORD
Chicago
CA $308 Roundtrip, found 5 hours ago
CA $308
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed., Sep. 3 from Calgary to Chicago, returning Wed., Sep. 10, priced at CA $308 found 5 hours ago
Wed., Sep. 3 - Wed., Sep. 17
YYC
Calgary
ORD
Chicago
CA $308 Roundtrip, found 5 hours ago
CA $308
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed., Sep. 3 from Calgary to Chicago, returning Wed., Sep. 17, priced at CA $308 found 5 hours ago
Mon., Sep. 29 - Mon., Oct. 6
YYC
Calgary
ORD
Chicago
CA $310 Roundtrip, found 2 days ago
CA $310
Roundtrip
found 2 days ago
Select Air Canada flight, departing Mon., Sep. 29 from Calgary to Chicago, returning Mon., Oct. 6, priced at CA $310 found 2 days ago

O'Hare Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 8
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 8
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
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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.