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Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 164

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
2 May — 9 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in April or May, booked 43 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Calgary to O'Hare Intl

Enter your travel dates to find the best prices.

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 2 April 2026.

Fri 17/49:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 24/42:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 31/3C$ 271
Wed 20/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/3C$ 276
Fri 22/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 31/3C$ 285
Fri 22/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/4C$ 315
Fri 29/56:45 a.m.
YYC
-
ORD
1 stop12h 36m
American Airlines
Mon 1/68:55 p.m.
ORD
-
YYC
Nonstop3h 48m
American Airlines
Deal found 30/3C$ 317
Sat 23/512:28 p.m.
YYC
-
ORD
Nonstop3h 37m
United Airlines
Tue 26/57:42 p.m.
ORD
-
YYC
Nonstop3h 55m
United Airlines
Deal found 1/4C$ 332
Fri 17/45:35 a.m.
YYC
-
ORD
1 stop8h 40m
Multiple Airlines
Fri 24/42:20 p.m.
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 31/3C$ 333
Thu 28/56:15 a.m.
YYC
-
ORD
Nonstop3h 30m
American Airlines
Sat 6/68:50 p.m.
ORD
-
YYC
Nonstop3h 48m
American Airlines
Deal found 2/4C$ 335
Fri 22/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 28/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 28/3C$ 336
Mon 18/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 31/3C$ 338
Wed 22/47:40 a.m.
YYC
-
ORD
2 stops11h 12m
Delta
Wed 29/42:09 p.m.
ORD
-
YYC
1 stop9h 51m
Delta
Deal found 31/3C$ 339

Find 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 2 April 2026.

Round-trip from

C$ 271

One-way from

C$ 164

Popular in

July

Cheapest in

April

Average price

C$ 297

Good round-trip deal

C$ 404 or less

Good one-way deal

C$ 339 or less
WestJet
  • WestJet
  • 17/4-24/4
  • Nonstop
  • 7h 30m total
  • Calgary to Chicago
Search Deals
WestJet
  • WestJet
  • 29/5
  • Nonstop
  • 3h 40m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Calgary to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Calgary to Chicago O'Hare Intl.
Search Deals

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 629,999 searches. Data last updated 2 April 2026.
Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 22/4

7:40 a.m.-7:52 p.m.

2 stops11h 12m

Chicago O'Hare Intl

Wed 29/4

12:14 p.m.-11:00 p.m.

2 stops11h 46m

C$ 339

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 27/8

8:30 a.m.-1:05 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 28/8

5:00 a.m.-6:30 p.m.

1 stop14h 30m

C$ 357

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 12/8

7:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Tue 18/8

1:55 p.m.-11:06 p.m.

1 stop10h 11m

C$ 364

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/6

6:45 a.m.-4:51 p.m.

1 stop9h 06m

Chicago O'Hare Intl

Thu 25/6

12:27 p.m.-8:38 p.m.

1 stop9h 11m

C$ 379

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 17/9

7:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Sun 20/9

1:55 p.m.-11:06 p.m.

1 stop10h 11m

C$ 389

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 29/7

6:45 a.m.-4:59 p.m.

1 stop9h 14m

Chicago O'Hare Intl

Mon 3/8

2:02 p.m.-10:59 p.m.

1 stop9h 57m

C$ 406

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 18/4

7:40 a.m.-7:52 p.m.

2 stops11h 12m

Chicago O'Hare Intl

Mon 20/4

12:14 p.m.-8:40 p.m.

1 stop9h 26m

C$ 479
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 3/6

8:30 a.m.-1:07 p.m.

Nonstop3h 37m

Chicago O'Hare Intl

Sun 7/6

7:42 p.m.-10:37 p.m.

Nonstop3h 55m

C$ 504

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 17/5

6:45 a.m.-4:51 p.m.

1 stop9h 06m

Chicago O'Hare Intl

Sat 30/5

6:24 a.m.-4:10 p.m.

2 stops10h 46m

C$ 539
Cheapest one-way
Quickest one-way

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 27/5

8:30 a.m.-1:07 p.m.

Nonstop3h 37m

C$ 183

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/3

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 2 April 2026.

The best time to book flights from Calgary to Chicago O'Hare Intl Airport is 43 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 133). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 225). 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 2 April 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago O'Hare Intl Airport as you normally would.

How much does it cost to fly round-trip from Calgary to Chicago O'Hare Intl Airport?

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 2 April 2026.
See what other customers who have flown with Delta,United Airlines, andWestJet from Calgary to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,370 reviews
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,533 reviews
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,309 reviews
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,549 reviews
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,881 reviews
Delta
7.9
Good
8,370 reviews
Check prices

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 6 outbound flights to Chicago O'Hare Intl per day. 5 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?

    A quick flight from Calgary to Chicago O'Hare Intl Airport can take about 3h 35m. Delta provides one of the quickest options available for as low as C$ 357. Airlines will cover a distance of 2223 km. Both multi-stop and direct flights can be found to your destination and back.

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

    Cheapflights users have booked flights from Calgary to Chicago O'Hare Intl Airport round-trip from C$ 121. Other airlines that can offer you cheap pricing are United Airlines, from C$ 126, and Delta, from C$ 149. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 67% 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?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 136. United Airlines flights start at C$ 164 while deals on American Airlines start at C$ 168 one-way.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Calgary to Chicago O'Hare Intl Airport on time: Scandinavian Airlines (83%), WestJet (82%), Delta (76%).

  • 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 C$ 1,271, our data indicates the cheapest price to be C$ 150. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 332.

  • 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, April is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 133). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 225). 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

Travelling 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
Evanston
Des Plaines
Skokie
Downers Grove
Elk Grove Village
Racine
Naperville
Bolingbrook
Romeoville
Schaumburg

Browse thousands of different options on Cheapflights for your next trip

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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
Edmonton to Midway flights
Calgary to Midway flights
Fort McMurray to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Grande Prairie to Midway flights

Top 5 airlines flying from Calgary to O'Hare Intl

Discover the top 5 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 629,999 searches. Data last updated 2 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 121AverageC$ 381FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 126AverageC$ 376FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 149AverageC$ 378FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 172AverageC$ 362FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 178AverageC$ 341FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Calgary to O'Hare Intl?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to O'Hare Intl from Calgary today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Calgary to O'Hare Intl?

Cheapflights simply makes it quick and affordable to book flights from Calgary to O'Hare Intl by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Calgary to O'Hare Intl with no change fees?

Yes, we can. To see specific flights from Calgary to O'Hare Intl with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Calgary to O'Hare Intl become cheaper?

Of course! You can now track prices for flights from Calgary to O'Hare Intl and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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