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 $249 round trip and CA $157 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Sep. 3 - Tue, Sep. 16
YYC
Calgary
ORD
Chicago
CA $249 Roundtrip, found 2 days ago
CA $249
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, Sep. 3 from Calgary to Chicago, returning Tue, Sep. 16, priced at CA $249 found 2 days ago
Thu, Sep. 4 - Mon, Sep. 15
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 7 hours ago
CA $256
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Sep. 4 from Calgary to Chicago, returning Mon, Sep. 15, priced at CA $256 found 7 hours ago
Thu, Oct. 16 - Sat, Oct. 18
YYC
Calgary
ORD
Chicago
CA $260 Roundtrip, found 1 day ago
CA $260
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Oct. 16 from Calgary to Chicago, returning Sat, Oct. 18, priced at CA $260 found 1 day ago
Wed, Sep. 24 - Mon, Sep. 29
YYC
Calgary
ORD
Chicago
CA $260 Roundtrip, just found
CA $260
Roundtrip
just found
Select WestJet flight, departing Wed, Sep. 24 from Calgary to Chicago, returning Mon, Sep. 29, priced at CA $260 just found
Thu, Sep. 4 - Mon, Sep. 15
YYC
Calgary
ORD
Chicago
CA $264 Roundtrip, found 7 hours ago
CA $264
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Sep. 4 from Calgary to Chicago, returning Mon, Sep. 15, priced at CA $264 found 7 hours ago
Sun, Oct. 26 - Thu, Oct. 30
YYC
Calgary
ORD
Chicago
CA $268 Roundtrip, found 1 day ago
CA $268
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Oct. 26 from Calgary to Chicago, returning Thu, Oct. 30, priced at CA $268 found 1 day ago
Mon, Oct. 20 - Fri, Oct. 24
YYC
Calgary
ORD
Chicago
CA $270 Roundtrip, found 1 day ago
CA $270
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Oct. 20 from Calgary to Chicago, returning Fri, Oct. 24, priced at CA $270 found 1 day ago
Thu, Sep. 4 - Sat, Sep. 20
YYC
Calgary
ORD
Chicago
CA $270 Roundtrip, found 2 days ago
CA $270
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Sep. 4 from Calgary to Chicago, returning Sat, Sep. 20, priced at CA $270 found 2 days ago
Mon, Sep. 8 - Thu, Sep. 11
YYC
Calgary
ORD
Chicago
CA $274 Roundtrip, found 2 days ago
CA $274
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Sep. 8 from Calgary to Chicago, returning Thu, Sep. 11, priced at CA $274 found 2 days ago
Sun, Sep. 7 - Tue, Sep. 9
YYC
Calgary
ORD
Chicago
CA $275 Roundtrip, found 1 day ago
CA $275
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Sep. 7 from Calgary to Chicago, returning Tue, Sep. 9, priced at CA $275 found 1 day ago

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

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
per person
Sep 22 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
per person
Sep 22 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
per person
Sep 22 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
per person
Sep 22 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Sep 20 - Sep 22
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.