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O'Hare Intl

$113+ Cheap flights from Calgary (YYC) to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in May or April, booked 43 days in advance, depart on a Sunday or Wednesday and return on a Thursday

Cheap flight deals from Calgary to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 20, 2025.

Round-trip from

$156
(FlightHub)

One-way from

$113
(Air Canada)

Popular in

December

Cheapest in

May

Average price

$325

Good round-trip deal

$161 or less

Good one-way deal

$204 or less
From Calgary to Chicago O'Hare Intl
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One-way flight from Calgary to Chicago O'Hare Intl
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Highest demand for flights based on searches. 21% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Calgary to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Calgary to Chicago O'Hare Intl.
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Find flight deals from Calgary to O'Hare Intl

Cheapest flights from Calgary to O'Hare Intl
Explore the most affordable flight options available from Calgary to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/18$156
This KAYAK deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/19$165
This Air Canada deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/151:10 amYYC - ORD
1 stop7h 41mAir Canada
Tue 9/233:50 pmORD - YYC
1 stop8h 32mAir Canada
Deal found 8/18$174
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:10 amYYC - ORD
1 stop7h 41mMultiple Airlines
Fri 10/105:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 8/18$175
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1812:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/20$176
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:10 amYYC - ORD
1 stop7h 41mMultiple Airlines
Thu 10/95:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 8/18$177
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:10 amYYC - ORD
1 stop7h 41mAir Canada
Sat 10/113:35 pmORD - YYC
1 stop8h 41mAir Canada
Deal found 8/20$178
This deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:15 pmYYC - ORD
Nonstop3h 28mWestJet
Thu 10/235:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/18$180
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2812:37 pmYYC - ORD
Nonstop3h 33mUnited Airlines
Fri 10/311:55 pmORD - YYC
1 stop8h 58mUnited Airlines
Deal found 8/20$185
This Trip.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/111:40 pmYYC - ORD
1 stop16h 48mMultiple Airlines
Fri 12/52:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 8/20$188

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

Fly from

Calgary

Fly to

O'Hare Intl

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$156

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 11/21

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 11/24

2:20 pm-5:15 pm

Nonstop3h 55m

$156

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/16

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$165

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/15

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Tue 9/23

3:50 pm-11:22 pm

1 stop8h 32m

$174

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/1

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Fri 10/10

5:30 pm-8:19 pm

Nonstop3h 49m

$175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 10/18

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$176

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/1

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Thu 10/9

5:30 pm-8:19 pm

Nonstop3h 49m

$177

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/3

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Sat 10/11

3:35 pm-11:16 pm

1 stop8h 41m

$178

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/16

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Thu 10/23

5:30 pm-8:19 pm

Nonstop3h 49m

$180

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/28

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Fri 10/31

8:45 am-11:35 am

Nonstop3h 50m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 23 results
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The best insider tips for Calgary to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Calgary to Chicago O'Hare Intl Airport trip
Airports
YYC

For a quick ride to downtown Calgary, use Route 300 rapid transit bus from YYC's terminals.

Read more about YYCby Jenna Scatena
ORD

Consider taking the “L” train from ORD to downtown Chicago to avoid traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Jenna Scatena

Jenna Scatena

Expert on YYC

Jenna Scatena

Jenna Scatena

Journalist and Travel Writer, Jenna Scatena is an award-winning travel writer with a love for sharing stories and exploring new places, especially by Vespa. Though she's from San Francisco, she has spent a significant chunk of her vacation days over the last decade eating her way through Texas and sleeping in hotels around the world—especially in California, the Middle East, and Europe.

Read more

Best time to book a flight from Calgary to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Calgary to Chicago O'Hare Intl Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Calgary to O'Hare Intl. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago O'Hare Intl Airport, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Calgary to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of $245). Flying from Calgary to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YYC to ORD?

Find hourly flight availability from Calgary to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Calgary to Chicago O'Hare Intl Airport in the morning. If you’re flexible enough to do this you can expect to save up to 45% on your trip compared to booking a flight at noon.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated August 20, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and WestJet from Calgary to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,040 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Calgary to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago O'Hare Intl?

    For a flight from Calgary to Chicago O'Hare Intl, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 13 outbound flights to Chicago O'Hare Intl per day. 4 airlines have flights to Chicago O'Hare Intl from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago O'Hare Intl Airport?

    Departing from Calgary to Chicago O'Hare Intl Airport will take you 3h 28m. There are 1381 mi between Calgary and Chicago O'Hare Intl Airport. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Calgary to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from Calgary to Chicago O'Hare Intl Airport is Air Canada. Our recent data shows that you can find tickets from as low as $109 on this airline. Additional options worth looking into are WestJet and United Airlines, starting at $137 and $239 round-trip. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 61% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Calgary to Chicago O'Hare Intl Airport?

    The top 3 most reliable airlines when flying from Calgary to Chicago O'Hare Intl Airport are Avianca (80%), Air Canada (72%) and United Airlines (72%).

  • What are the cheapest flights from Calgary to Chicago O'Hare Intl Airport?

    Looking for the cheapest flight from Calgary to Chicago O'Hare Intl Airport? While on average our users pay $309, our data indicates the cheapest price to be $115. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $192.

  • Can I find deals for flights from Calgary to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Calgary to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to O'Hare Intl.

  • Can I find deals for business class flights from Calgary to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Calgary to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of $245). Flying from Calgary to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Beloit
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Naperville
Merrillville
Elk Grove Village
Downers Grove
Evanston
Lake Geneva
Joliet

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Alternative routes for Calgary to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Edmonton to Midway flights
Medicine Hat to O'Hare Intl flights
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Top 4 airlines flying from Calgary to O'Hare Intl

Discover the top 4 airlines that operate flights from Calgary to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$137Average$222FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$239Average$468FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$250Average$376FlexibilityNo cancel feeOn-time71%

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