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 $262 round trip and CA $166 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 26 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
CA $262 Roundtrip, found 3 days ago
CA $262
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Dec 26 from Calgary to Chicago, returning Mon, Jan 5, priced at CA $262 found 3 days ago
Mon, Dec 22 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
CA $269 Roundtrip, found 2 days ago
CA $269
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Dec 22 from Calgary to Chicago, returning Mon, Jan 5, priced at CA $269 found 2 days ago
Mon, Jan 5 - Mon, Jan 12
YYC
Calgary
ORD
Chicago
CA $272 Roundtrip, found 3 days ago
CA $272
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Jan 5 from Calgary to Chicago, returning Mon, Jan 12, priced at CA $272 found 3 days ago
Fri, Dec 19 - Fri, Jan 2
YYC
Calgary
ORD
Chicago
CA $273 Roundtrip, found 4 days ago
CA $273
Roundtrip
found 4 days ago
Select WestJet flight, departing Fri, Dec 19 from Calgary to Chicago, returning Fri, Jan 2, priced at CA $273 found 4 days ago
Mon, Dec 29 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
CA $281 Roundtrip, found 1 day ago
CA $281
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Dec 29 from Calgary to Chicago, returning Mon, Jan 5, priced at CA $281 found 1 day ago
Fri, Jan 9 - Fri, Jan 23
YYC
Calgary
ORD
Chicago
CA $292 Roundtrip, found 12 hours ago
CA $292
Roundtrip
found 12 hours ago
Select WestJet flight, departing Fri, Jan 9 from Calgary to Chicago, returning Fri, Jan 23, priced at CA $292 found 12 hours ago
Wed, Jan 7 - Sat, Jan 24
YYC
Calgary
ORD
Chicago
CA $294 Roundtrip, found 12 hours ago
CA $294
Roundtrip
found 12 hours ago
Select Air Canada flight, departing Wed, Jan 7 from Calgary to Chicago, returning Sat, Jan 24, priced at CA $294 found 12 hours ago
Fri, Dec 5 - Fri, Jan 9
YYC
Calgary
ORD
Chicago
CA $295 Roundtrip, found 1 day ago
CA $295
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Dec 5 from Calgary to Chicago, returning Fri, Jan 9, priced at CA $295 found 1 day ago
Mon, Nov 24 - Fri, Nov 28
YYC
Calgary
ORD
Chicago
CA $298 Roundtrip, found 10 hours ago
CA $298
Roundtrip
found 10 hours ago
Select WestJet flight, departing Mon, Nov 24 from Calgary to Chicago, returning Fri, Nov 28, priced at CA $298 found 10 hours ago
Tue, Nov 25 - Wed, Nov 26
YYC
Calgary
ORD
Chicago
CA $301 Roundtrip, found 3 days ago
CA $301
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, Nov 25 from Calgary to Chicago, returning Wed, Nov 26, priced at CA $301 found 3 days ago

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

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was CA $898, price is now CA $639 per person
CA $639
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $1,158, price is now CA $768 per person
CA $768
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was CA $2,070, price is now CA $1,395 per person
CA $1,395
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was CA $2,599, price is now CA $1,848 per person
CA $1,848
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was CA $1,326, price is now CA $946 per person
CA $946
per person
Dec 12 - Dec 16
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.

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.