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 $269 round trip and CA $167 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Feb 26 - Tue, Mar 3
YYC
Calgary
ORD
Chicago
CA $269 Roundtrip, found 2 days ago
CA $269
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Feb 26 from Calgary to Chicago, returning Tue, Mar 3, priced at CA $269 found 2 days ago
Tue, Feb 24 - Tue, Mar 3
YYC
Calgary
ORD
Chicago
CA $270 Roundtrip, found 2 days ago
CA $270
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Feb 24 from Calgary to Chicago, returning Tue, Mar 3, priced at CA $270 found 2 days ago
Mon, Jan 12 - Fri, Jan 23
YYC
Calgary
ORD
Chicago
CA $272 Roundtrip, found 17 hours ago
CA $272
Roundtrip
found 17 hours ago
Select WestJet flight, departing Mon, Jan 12 from Calgary to Chicago, returning Fri, Jan 23, priced at CA $272 found 17 hours ago
Mon, Apr 6 - Fri, Apr 10
YYC
Calgary
ORD
Chicago
CA $275 Roundtrip, found 1 day ago
CA $275
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Apr 6 from Calgary to Chicago, returning Fri, Apr 10, priced at CA $275 found 1 day ago
Mon, Apr 6 - Mon, Apr 13
YYC
Calgary
ORD
Chicago
CA $278 Roundtrip, found 1 day ago
CA $278
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Apr 6 from Calgary to Chicago, returning Mon, Apr 13, priced at CA $278 found 1 day ago
Mon, Feb 23 - Mon, Mar 2
YYC
Calgary
ORD
Chicago
CA $284 Roundtrip, found 2 days ago
CA $284
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Feb 23 from Calgary to Chicago, returning Mon, Mar 2, priced at CA $284 found 2 days ago
Fri, Feb 27 - Mon, Mar 2
YYC
Calgary
ORD
Chicago
CA $285 Roundtrip, found 2 days ago
CA $285
Roundtrip
found 2 days ago
Select WestJet flight, departing Fri, Feb 27 from Calgary to Chicago, returning Mon, Mar 2, priced at CA $285 found 2 days ago
Thu, Jun 4 - Mon, Jun 8
YYC
Calgary
ORD
Chicago
CA $297 Roundtrip, found 1 day ago
CA $297
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Jun 4 from Calgary to Chicago, returning Mon, Jun 8, priced at CA $297 found 1 day ago
Fri, May 22 - Sun, May 24
YYC
Calgary
ORD
Chicago
CA $298 Roundtrip, found 3 days ago
CA $298
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, May 22 from Calgary to Chicago, returning Sun, May 24, priced at CA $298 found 3 days ago
Sat, Jan 10 - Sun, Jan 11
YYC
Calgary
ORD
Chicago
CA $309 Roundtrip, found 17 hours ago
CA $309
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Jan 10 from Calgary to Chicago, returning Sun, Jan 11, priced at CA $309 found 17 hours ago

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

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $792, price is now CA $582 per person
CA $582
per person
Jan 30 - Feb 2
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 $924, price is now CA $660 per person
CA $660
per person
Jan 30 - Feb 2
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 $1,274, price is now CA $941 per person
CA $941
per person
Feb 10 - Feb 13
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Price was CA $1,559, price is now CA $1,160 per person
CA $1,160
per person
Jan 30 - Feb 2
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 $1,637, price is now CA $1,222 per person
CA $1,222
per person
Jan 30 - Feb 2
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.