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 $343 round trip and CA $206 one way. Prices and availability subject to change. Additional terms may apply.

Wed, May 20 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $343 Roundtrip, found 20 hours ago
CA $343
Roundtrip
found 20 hours ago
Select WestJet flight, departing Wed, May 20 from Calgary to Chicago, returning Wed, May 27, priced at CA $343 found 20 hours ago
Sun, May 24 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $344 Roundtrip, found 4 days ago
CA $344
Roundtrip
found 4 days ago
Select WestJet flight, departing Sun, May 24 from Calgary to Chicago, returning Wed, May 27, priced at CA $344 found 4 days ago
Tue, Apr 28 - Wed, Apr 29
YYC
Calgary
ORD
Chicago
CA $349 Roundtrip, found 1 day ago
CA $349
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 28 from Calgary to Chicago, returning Wed, Apr 29, priced at CA $349 found 1 day ago
Sun, May 24 - Sat, May 30
YYC
Calgary
ORD
Chicago
CA $361 Roundtrip, found 6 days ago
CA $361
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, May 24 from Calgary to Chicago, returning Sat, May 30, priced at CA $361 found 6 days ago
Tue, Apr 28 - Thu, Apr 30
YYC
Calgary
ORD
Chicago
CA $363 Roundtrip, found 1 day ago
CA $363
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Apr 28 from Calgary to Chicago, returning Thu, Apr 30, priced at CA $363 found 1 day ago
Thu, Apr 23 - Wed, Apr 29
YYC
Calgary
ORD
Chicago
CA $370 Roundtrip, found 1 day ago
CA $370
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Apr 23 from Calgary to Chicago, returning Wed, Apr 29, priced at CA $370 found 1 day ago
Thu, Apr 16 - Tue, Apr 21
YYC
Calgary
ORD
Chicago
CA $372 Roundtrip, found 2 days ago
CA $372
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Apr 16 from Calgary to Chicago, returning Tue, Apr 21, priced at CA $372 found 2 days ago
Sun, May 10 - Sat, May 16
YYC
Calgary
ORD
Chicago
CA $373 Roundtrip, found 4 days ago
CA $373
Roundtrip
found 4 days ago
Select WestJet flight, departing Sun, May 10 from Calgary to Chicago, returning Sat, May 16, priced at CA $373 found 4 days ago
Sun, Apr 26 - Tue, Apr 28
YYC
Calgary
ORD
Chicago
CA $378 Roundtrip, found 1 day ago
CA $378
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Apr 26 from Calgary to Chicago, returning Tue, Apr 28, priced at CA $378 found 1 day ago
Wed, Apr 22 - Sat, Apr 25
YYC
Calgary
ORD
Chicago
CA $386 Roundtrip, found 3 days ago
CA $386
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 22 from Calgary to Chicago, returning Sat, Apr 25, priced at CA $386 found 3 days ago

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

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was CA $922, price is now CA $799 per person
CA $799
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was CA $1,481, price is now CA $1,128 per person
CA $1,128
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was CA $1,253, price is now CA $1,051 per person
CA $1,051
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Price was CA $1,293, price is now CA $1,113 per person
CA $1,113
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Hotel Arista

Hotel Arista

4.5 out of 5
Price was CA $1,111, price is now CA $959 per person
CA $959
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop 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.

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*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.