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 $367 round trip and CA $229 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Jun 18 - Mon, Jun 29
YYC
Calgary
ORD
Chicago
CA $367 Roundtrip, found 1 day ago
CA $367
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jun 18 from Calgary to Chicago, returning Mon, Jun 29, priced at CA $367 found 1 day ago
Tue, Aug 18 - Mon, Aug 24
YYC
Calgary
ORD
Chicago
CA $380 Roundtrip, found 23 hours ago
CA $380
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Aug 18 from Calgary to Chicago, returning Mon, Aug 24, priced at CA $380 found 23 hours ago
Wed, Aug 19 - Sat, Aug 22
YYC
Calgary
ORD
Chicago
CA $380 Roundtrip, found 7 hours ago
CA $380
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 19 from Calgary to Chicago, returning Sat, Aug 22, priced at CA $380 found 7 hours ago
Wed, Aug 19 - Sat, Aug 22
YYC
Calgary
ORD
Chicago
CA $388 Roundtrip, found 7 hours ago
CA $388
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Wed, Aug 19 from Calgary to Chicago, returning Sat, Aug 22, priced at CA $388 found 7 hours ago
Tue, Oct 27 - Sun, Nov 1
YYC
Calgary
ORD
Chicago
CA $390 Roundtrip, found 5 days ago
CA $390
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 27 from Calgary to Chicago, returning Sun, Nov 1, priced at CA $390 found 5 days ago
Wed, Aug 19 - Sat, Aug 22
YYC
Calgary
ORD
Chicago
CA $395 Roundtrip, found 7 hours ago
CA $395
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Wed, Aug 19 from Calgary to Chicago, returning Sat, Aug 22, priced at CA $395 found 7 hours ago
Sat, Nov 21 - Sun, Jan 31
YYC
Calgary
ORD
Chicago
CA $405 Roundtrip, found 4 days ago
CA $405
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Nov 21 from Calgary to Chicago, returning Sun, Jan 31, priced at CA $405 found 4 days ago
Tue, Jun 9 - Sat, Jun 13
YYC
Calgary
ORD
Chicago
CA $405 Roundtrip, found 1 hour ago
CA $405
Roundtrip
found 1 hour ago
Select WestJet flight, departing Tue, Jun 9 from Calgary to Chicago, returning Sat, Jun 13, priced at CA $405 found 1 hour ago
Tue, Oct 27 - Sun, Nov 1
YYC
Calgary
ORD
Chicago
CA $406 Roundtrip, found 5 days ago
CA $406
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 27 from Calgary to Chicago, returning Sun, Nov 1, priced at CA $406 found 5 days ago
Wed, Aug 19 - Mon, Aug 24
YYC
Calgary
ORD
Chicago
CA $408 Roundtrip, found 19 hours ago
CA $408
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Aug 19 from Calgary to Chicago, returning Mon, Aug 24, priced at CA $408 found 19 hours ago

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

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was CA $1,644, price is now CA $1,105 per person
CA $1,105
per person
Jun 30 - Jul 4
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 $1,569, price is now CA $1,123 per person
CA $1,123
per person
Jun 30 - Jul 4
found 1 day 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
Price was CA $2,857, price is now CA $2,074 per person
CA $2,074
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Price was CA $2,436, price is now CA $1,784 per person
CA $1,784
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Price was CA $4,339, price is now CA $3,239 per person
CA $3,239
per person
Jun 21 - Jun 26
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.

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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.