Cheap Flights From Calgary Intl. (YYC) To O'Hare Intl. (ORD)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Calgary (YYC) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $238 round trip and CA $151 one way. Prices and availability subject to change. Additional terms may apply.

Sun, Oct 26 - Fri, Oct 31
YYC
Calgary
ORD
Chicago
CA $238 Roundtrip, found 10 hours ago
CA $238
Roundtrip
found 10 hours ago
Select WestJet flight, departing Sun, Oct 26 from Calgary to Chicago, returning Fri, Oct 31, priced at CA $238 found 10 hours ago
Mon, Nov 3 - Mon, Nov 10
YYC
Calgary
ORD
Chicago
CA $246 Roundtrip, found 5 days ago
CA $246
Roundtrip
found 5 days ago
Select WestJet flight, departing Mon, Nov 3 from Calgary to Chicago, returning Mon, Nov 10, priced at CA $246 found 5 days ago
Mon, Mar 30 - Fri, Apr 3
YYC
Calgary
ORD
Chicago
CA $249 Roundtrip, found 1 day ago
CA $249
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Mar 30 from Calgary to Chicago, returning Fri, Apr 3, priced at CA $249 found 1 day ago
Mon, Nov 17 - Fri, Nov 21
YYC
Calgary
ORD
Chicago
CA $250 Roundtrip, found 15 hours ago
CA $250
Roundtrip
found 15 hours ago
Select WestJet flight, departing Mon, Nov 17 from Calgary to Chicago, returning Fri, Nov 21, priced at CA $250 found 15 hours ago
Fri, Oct 17 - Thu, Oct 23
YYC
Calgary
ORD
Chicago
CA $251 Roundtrip, found 4 days ago
CA $251
Roundtrip
found 4 days ago
Select WestJet flight, departing Fri, Oct 17 from Calgary to Chicago, returning Thu, Oct 23, priced at CA $251 found 4 days ago
Thu, Oct 23 - Mon, Oct 27
YYC
Calgary
ORD
Chicago
CA $255 Roundtrip, found 4 hours ago
CA $255
Roundtrip
found 4 hours ago
Select WestJet flight, departing Thu, Oct 23 from Calgary to Chicago, returning Mon, Oct 27, priced at CA $255 found 4 hours ago
Fri, Oct 24 - Sun, Oct 26
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 8 hours ago
CA $256
Roundtrip
found 8 hours ago
Select WestJet flight, departing Fri, Oct 24 from Calgary to Chicago, returning Sun, Oct 26, priced at CA $256 found 8 hours ago
Wed, Oct 22 - Sat, Oct 25
YYC
Calgary
ORD
Chicago
CA $257 Roundtrip, found 5 days ago
CA $257
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Oct 22 from Calgary to Chicago, returning Sat, Oct 25, priced at CA $257 found 5 days ago
Fri, Dec 5 - Mon, Dec 8
YYC
Calgary
ORD
Chicago
CA $260 Roundtrip, found 13 hours ago
CA $260
Roundtrip
found 13 hours ago
Select WestJet flight, departing Fri, Dec 5 from Calgary to Chicago, returning Mon, Dec 8, priced at CA $260 found 13 hours ago
Fri, Oct 17 - Sun, Oct 19
YYC
Calgary
ORD
Chicago
CA $268 Roundtrip, found 13 hours ago
CA $268
Roundtrip
found 13 hours ago
Select WestJet flight, departing Fri, Oct 17 from Calgary to Chicago, returning Sun, Oct 19, priced at CA $268 found 13 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 $885, price is now CA $666 per person
CA $666
per person
Oct 24 - Oct 26
found 11 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $1,335, price is now CA $913 per person
CA $913
per person
Oct 24 - Oct 26
found 11 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $930, price is now CA $675 per person
CA $675
per person
Oct 24 - Oct 26
found 11 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was CA $1,086, price is now CA $796 per person
CA $796
per person
Oct 24 - Oct 26
found 11 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Price was CA $1,229, price is now CA $989 per person
CA $989
per person
Nov 7 - Nov 11
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Calgary Intl. to O'Hare Intl.
View all trips

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.