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O'Hare Intl

$121+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 Friday

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 July 3, 2025.

Round-trip from

$143
(Justfly.com)

One-way from

$121
(WestJet)

Popular in

December

Cheapest in

May

Average price

$314

Good round-trip deal

$340 or less

Good one-way deal

$208 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. 23% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Justfly.com deal was found by Cheapflights users on 7/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:15 pmYYC - ORD
Nonstop3h 28mWestJet
Thu 9/115:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 7/2$143
This Mytrip deal was found by Cheapflights users on 7/2. 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 8/201:05 amYYC - ORD
1 stop7h 41mMultiple Airlines
Wed 8/275:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 7/2$187
This Booking.com deal was found by Cheapflights users on 7/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/201:05 amYYC - ORD
1 stop7h 41mAir Canada
Wed 8/273:50 pmORD - YYC
1 stop9h 20mAir Canada
Deal found 7/2$193
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:55 amYYC - ORD
2 stops12h 40mDelta
Wed 9/31:00 pmORD - YYC
1 stop10h 57mDelta
Deal found 7/2$227
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Sat 10/189:49 amORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 7/2$246

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 July 3, 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

Mon 9/8

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Thu 9/11

5:30 pm-8:19 pm

Nonstop3h 49m

$143

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 8/20

1:05 am-9:46 am

1 stop7h 41m

Chicago O'Hare Intl

Wed 8/27

5:30 pm-8:19 pm

Nonstop3h 49m

$187

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 8/20

1:05 am-9:46 am

1 stop7h 41m

Chicago O'Hare Intl

Wed 8/27

3:50 pm-12:10 am

1 stop9h 20m

$193

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/30

7:55 am-9:35 pm

2 stops12h 40m

Chicago O'Hare Intl

Wed 9/3

1:00 pm-10:57 pm

1 stop10h 57m

$227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 8/19

6:15 am-8:41 pm

1 stop13h 26m

$123

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 9/10

1:10 am-9:51 am

1 stop7h 41m

$124

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 8/8

6:45 am-7:24 am

1 stop23h 39m

$143

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 9/11

8:55 am-12:00 am

1 stop14h 05m

$162

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 8/24

6:40 am-5:04 pm

1 stop9h 24m

$167

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 8/19

6:00 am-11:39 pm

2 stops16h 39m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 June 27, 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 July 3, 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 27% on your trip compared to booking a flight at noon.

Weekly flight availability from Calgary to Chicago O'Hare Intl Airport

Explore weekly flight availability from Calgary to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 3, 2025.

The most flights from YYC to ORD are scheduled on a Wednesday (15 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).

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 July 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United Airlines 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
WestJet
7.2
Good
2,917 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 9 outbound flights to Chicago O'Hare Intl per day. 4 airlines have flights to Chicago O'Hare Intl from Calgary on a regular basis.

  • 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 WestJet. Our recent data shows that you can find tickets from as low as $143 on this airline. Additional options worth looking into are American Airlines and Air Canada, starting at $192 and $193 round-trip. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 47% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Calgary to Chicago O'Hare Intl Airport one-way?

    $121 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from $123 and $124, respectively.

  • 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 (93%), Envoy Air (85%) and Air Canada (85%).

  • 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 $627, our data indicates the cheapest price to be $108. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $171.

  • 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 Calgary?

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Schaumburg
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Rosemont
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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.
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Edmonton to Midway flights
Grande Prairie to O'Hare Intl flights
Medicine Hat to O'Hare Intl flights

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$388FlexibilityNo cancel feeOn-time67%
WestJetCheapest$140Average$263FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$205Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$469FlexibilityNo cancel feeOn-time69%

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