YYC - ORD

$175 Find Cheap Flights from Calgary to Chicago O'Hare Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Calgary to O'Hare Intl departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$220
Typical prices: $267-$425
WestJet
Sat 8/29Mon 8/31
YYC - ORD • Non-stop
Cheapest one-way
$175
Typical prices: $145-$248
Air Canada
Fri 9/4
YYC - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Main Cabin Extra adds early boarding; United sells Priority Boarding.
WestJet Premium cabin includes two checked bags; airline Wi-Fi is paid or limited.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Every day
You can fly direct with American Airlines, United Airlines and WestJet. Average duration is 3h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Montreal (YUL)
Cheapest • Avg $250 (round-trip)
Toronto (YYZ)
Shortest trip • 7h 29m (one-way)
Insights
Insights
Insights
Insights
When to book
6 weeks
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 15% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Calgary to O'Hare Intl (YYC-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Calgary to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Calgary to O'Hare Intl

Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$220WestJet
Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$222WestJet
Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$250WestJet
Sat, Sep 5 - Sun, Sep 13
United Airlines Logo
8:30 am - 1:05 pm
YYC
-
ORD
3h 35mnonstop
United Airlines Logo
7:45 pm - 10:35 pm
ORD
-
YYC
3h 50mnonstop
$251United Airlines
Fri, Aug 28 - Mon, Aug 31
Air Canada Logo
1:00 am - 10:16 am
YYC
-
ORD
8h 16m
1 stop
Air Canada Logo
9:50 am - 1:56 am
ORD
-
YYC
17h 06m
1 stop
$257Air Canada
Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$258WestJet
Mon, Sep 28 - Mon, Oct 5
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$261WestJet
Sat, Aug 29 - Mon, Aug 31
Delta Logo
6:45 am - 3:30 pm
YYC
-
ORD
7h 45m
1 stop
Delta Logo
2:00 pm - 11:04 pm
ORD
-
YYC
10h 04m
1 stop
$262Delta
Fri, Oct 30 - Mon, Nov 2
Air Canada Logo
6:00 am - 3:38 pm
YYC
-
ORD
8h 38m
1 stop
Air Canada Logo
10:15 am - 6:54 pm
ORD
-
YYC
8h 39m
1 stop
$264Air Canada
Wed, Aug 12 - Fri, Sep 11
Delta Logo
6:45 am - 5:41 pm
YYC
-
ORD
9h 56m
1 stop
Delta Logo
2:05 pm - 11:06 pm
ORD
-
YYC
10h 01m
1 stop
$265Delta
Booking Insights

KAYAK's insights & trends for Calgary to O'Hare Intl flights

Get data-powered insights and trends into flights from Calgary to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Calgary to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Calgary to Chicago O'Hare Intl Airport departing in August.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from Calgary usually cost between $298 and $448 in August.
The lowest price found in the past 5 days was $220 on WestJet (Aug 29-Aug 31).

What’s the cheapest day of the week to fly from Calgary to Chicago O'Hare Airport?

The average price of all round-trip flights from Calgary to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from Calgary to Chicago O'Hare Airport, you should consider leaving on a Friday and avoid Wednesdays if you are looking for the best rates. For your return to Calgary, you’ll find the best rates on Fridays and the most expensive ones on Thursdays.

What is the cheapest month to fly from Calgary to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Calgary to Chicago O'Hare Intl Airport is November, where tickets cost $251 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $389 and $349 respectively.

Can I save money by flying with a layover from Calgary to Chicago O'Hare Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $324 on average.

How far in advance should I book a flight from Calgary to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Calgary to Chicago O'Hare Intl Airport, you should book around 6 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

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Expert advice

Expert advice for your flight from Calgary to O'Hare Intl

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet, United Airlines, Air Canada and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYC

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

Good to know

Low season

February

Cheapest flight

$175
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Calgary to Chicago O'Hare Airport

When to book flights from Calgary to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Calgary to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Calgary to Chicago O'Hare Airport flights

  • What is the cheapest flight from Calgary to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Calgary to Chicago O'Hare Intl Airport was $175 for a one-way ticket and $220 for a round-trip.

  • Do I need a passport to fly between Calgary and Chicago O'Hare Airport?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Calgary and on arrival in Chicago O'Hare Airport.

  • Which airports will I be using when flying from Calgary to Chicago O'Hare Airport?

    Calgary and Chicago O'Hare Airport are both served by 1 main airport. You will leave Calgary from Calgary and will be arriving at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Calgary to Chicago O'Hare Airport?

    American Airlines, WestJet, Air Canada, Lufthansa, and United Airlines offer inflight Wi-Fi service on the Calgary to Chicago O'Hare Airport flight route.

  • Which aircraft models fly most regularly from Calgary to Chicago O'Hare Airport?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Calgary to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Calgary to Chicago O'Hare Airport?

    oneworld, and Star Alliance are the airline alliances operating flights between Calgary and Chicago O'Hare Airport, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Calgary to Chicago O'Hare Airport?

    There are nonstop flights from Calgary to Chicago O'Hare Airport on a daily basis.

  • Which is the best airline for flights from Calgary to Chicago, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are United Airlines and WestJet. With an average price for the route of $424 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $273 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Calgary to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Calgary to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Calgary to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Calgary is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Calgary to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back to Calgary with another airline. Booking your flights between Calgary and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Calgary to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport from Calgary up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Calgary to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $229 or less one-way and $365 or less round-trip.

Prefer to fly direct from Calgary to Chicago O'Hare Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Calgary to Chicago O'Hare Intl.
Find which airlines fly direct from Calgary Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Calgary to Chicago O'Hare Intl

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Everything you need to know for your flight from Calgary to O'Hare Intl

Information on your arrival and departure airports

Calgary (YYC)
O'Hare Intl (ORD)