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 $417 round trip and CA $222 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Dec 3 - Sat, Dec 5
YYC
Calgary
ORD
Chicago
CA $417 Roundtrip, found 18 hours ago
CA $417
Roundtrip
found 18 hours ago
Select Delta flight, departing Thu, Dec 3 from Calgary to Chicago, returning Sat, Dec 5, priced at CA $417 found 18 hours ago
Wed, Oct 28 - Sun, Nov 1
YYC
Calgary
ORD
Chicago
CA $421 Roundtrip, found 18 hours ago
CA $421
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Oct 28 from Calgary to Chicago, returning Sun, Nov 1, priced at CA $421 found 18 hours ago
Tue, Oct 27 - Sun, Nov 1
YYC
Calgary
ORD
Chicago
CA $425 Roundtrip, found 18 hours ago
CA $425
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Oct 27 from Calgary to Chicago, returning Sun, Nov 1, priced at CA $425 found 18 hours ago
Wed, Dec 9 - Sat, Jan 9
YYC
Calgary
ORD
Chicago
CA $428 Roundtrip, found 3 days ago
CA $428
Roundtrip
found 3 days ago
Select United flight, departing Wed, Dec 9 from Calgary to Chicago, returning Sat, Jan 9, priced at CA $428 found 3 days ago
Sun, Oct 25 - Sat, Oct 31
YYC
Calgary
ORD
Chicago
CA $433 Roundtrip, found 18 hours ago
CA $433
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Sun, Oct 25 from Calgary to Chicago, returning Sat, Oct 31, priced at CA $433 found 18 hours ago
Wed, Dec 9 - Sat, Jan 9
YYC
Calgary
ORD
Chicago
CA $436 Roundtrip, found 3 days ago
CA $436
Roundtrip
found 3 days ago
Select United flight, departing Wed, Dec 9 from Calgary to Chicago, returning Sat, Jan 9, priced at CA $436 found 3 days ago
Fri, Oct 23 - Fri, Oct 30
YYC
Calgary
ORD
Chicago
CA $438 Roundtrip, found 3 days ago
CA $438
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Oct 23 from Calgary to Chicago, returning Fri, Oct 30, priced at CA $438 found 3 days ago
Sun, Oct 25 - Sat, Oct 31
YYC
Calgary
ORD
Chicago
CA $440 Roundtrip, found 18 hours ago
CA $440
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Sun, Oct 25 from Calgary to Chicago, returning Sat, Oct 31, priced at CA $440 found 18 hours ago
Wed, Dec 9 - Sat, Jan 9
YYC
Calgary
ORD
Chicago
CA $444 Roundtrip, found 3 days ago
CA $444
Roundtrip
found 3 days ago
Select Air Canada flight, departing Wed, Dec 9 from Calgary to Chicago, returning Sat, Jan 9, priced at CA $444 found 3 days ago
Wed, Oct 21 - Thu, Oct 29
YYC
Calgary
ORD
Chicago
CA $446 Roundtrip, found 4 days ago
CA $446
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Oct 21 from Calgary to Chicago, returning Thu, Oct 29, priced at CA $446 found 4 days ago

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

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was CA $1,137, price is now CA $862 per person
CA $862
per person
Nov 14 - Nov 18
found 1 day 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
Price was CA $1,860, price is now CA $1,229 per person
CA $1,229
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $1,982, price is now CA $1,357 per person
CA $1,357
per person
Nov 7 - Nov 11
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was CA $1,508, price is now CA $1,078 per person
CA $1,078
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was CA $2,719, price is now CA $2,025 per person
CA $2,025
per person
Nov 14 - Nov 18
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.