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 $380 round trip and CA $227 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Aug 14 - Tue, Aug 25
YYC
Calgary
ORD
Chicago
CA $380 Roundtrip, found 1 day ago
CA $380
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Aug 14 from Calgary to Chicago, returning Tue, Aug 25, priced at CA $380 found 1 day ago
Tue, Apr 6 - Mon, Apr 12
YYC
Calgary
ORD
Chicago
CA $383 Roundtrip, found 13 hours ago
CA $383
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Apr 6 from Calgary to Chicago, returning Mon, Apr 12, priced at CA $383 found 13 hours ago
Wed, Aug 12 - Sat, Aug 22
YYC
Calgary
ORD
Chicago
CA $388 Roundtrip, found 1 day ago
CA $388
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Aug 12 from Calgary to Chicago, returning Sat, Aug 22, priced at CA $388 found 1 day ago
Wed, Aug 12 - Wed, Aug 26
YYC
Calgary
ORD
Chicago
CA $395 Roundtrip, found 1 day ago
CA $395
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Aug 12 from Calgary to Chicago, returning Wed, Aug 26, priced at CA $395 found 1 day ago
Thu, Sep 3 - Mon, Sep 7
YYC
Calgary
ORD
Chicago
CA $401 Roundtrip, found 2 days ago
CA $401
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Sep 3 from Calgary to Chicago, returning Mon, Sep 7, priced at CA $401 found 2 days ago
Wed, Oct 21 - Fri, Oct 23
YYC
Calgary
ORD
Chicago
CA $401 Roundtrip, found 2 days ago
CA $401
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 21 from Calgary to Chicago, returning Fri, Oct 23, priced at CA $401 found 2 days ago
Thu, Jul 16 - Mon, Jul 27
YYC
Calgary
ORD
Chicago
CA $402 Roundtrip, found 5 days ago
CA $402
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jul 16 from Calgary to Chicago, returning Mon, Jul 27, priced at CA $402 found 5 days ago
Thu, Aug 13 - Fri, Aug 21
YYC
Calgary
ORD
Chicago
CA $408 Roundtrip, found 1 day ago
CA $408
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Aug 13 from Calgary to Chicago, returning Fri, Aug 21, priced at CA $408 found 1 day ago
Tue, Apr 6 - Sun, Apr 11
YYC
Calgary
ORD
Chicago
CA $412 Roundtrip, found 3 hours ago
CA $412
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Apr 6 from Calgary to Chicago, returning Sun, Apr 11, priced at CA $412 found 3 hours ago
Thu, Sep 3 - Mon, Sep 7
YYC
Calgary
ORD
Chicago
CA $412 Roundtrip, found 2 days ago
CA $412
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 3 from Calgary to Chicago, returning Mon, Sep 7, priced at CA $412 found 2 days ago

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

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was CA $1,564, price is now CA $1,131 per person
CA $1,131
per person
Jul 1 - 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 $2,241, price is now CA $1,477 per person
CA $1,477
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was CA $1,921, price is now CA $1,365 per person
CA $1,365
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $1,740, price is now CA $1,243 per person
CA $1,243
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
Price was CA $2,299, price is now CA $1,650 per person
CA $1,650
per person
Jun 25 - Jun 30
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.