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Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 241

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 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
1 Sep — 8 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in November or May, booked 45 days in advance, depart on a Friday or Thursday and return on a Thursday

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 August 2026.

Fri 25/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 29/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/7C$ 293
Tue 15/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 17/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 30/7C$ 294
Sun 20/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Tue 29/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 31/7C$ 303
Wed 21/1012:30 p.m.
YYC
-
ORD
Nonstop3h 35m
United Airlines
Sat 24/108:40 a.m.
ORD
-
YYC
Nonstop3h 48m
United Airlines
Deal found 31/7C$ 321
Sun 22/1112:37 p.m.
YYC
-
ORD
Nonstop3h 33m
United Airlines
Sat 28/118:40 a.m.
ORD
-
YYC
Nonstop3h 55m
United Airlines
Deal found 30/7C$ 331
Wed 21/1012:30 p.m.
YYC
-
ORD
Nonstop3h 35m
Multiple Airlines
Sat 24/103:40 p.m.
ORD
-
YYC
1 stop8h 47m
Multiple Airlines
Deal found 31/7C$ 332
Sat 19/91:00 a.m.
YYC
-
ORD
1 stop8h 15m
Air Canada
Tue 29/98:45 a.m.
ORD
-
YYC
1 stop8h 12m
Air Canada
Deal found 31/7C$ 333
Thu 24/91:00 a.m.
YYC
-
ORD
1 stop8h 15m
Air Canada
Fri 2/102:15 p.m.
ORD
-
YYC
1 stop9h 42m
Air Canada
Deal found 1/8C$ 338

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 August 2026.

Round-trip from

C$ 293

One-way from

C$ 241

Popular in

July

Cheapest in

November

Average price

C$ 489

Good round-trip deal

C$ 630 or less

Good one-way deal

C$ 346 or less
WestJet
  • WestJet
  • 25/9-29/9
  • Nonstop
  • 7h 35m total
  • Calgary to Chicago
Search Deals
WestJet
  • WestJet
  • 30/8
  • Nonstop
  • 3h 40m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 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

Sun 22/11

12:37 p.m.-4:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Sat 28/11

8:40 a.m.-12:35 p.m.

Nonstop3h 55m

C$ 331

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/10

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Mon 2/11

8:40 a.m.-12:35 p.m.

Nonstop3h 55m

C$ 475

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 22/11

7:14 a.m.-7:25 p.m.

2 stops12h 11m

Chicago O'Hare Intl

Sat 28/11

12:40 p.m.-9:58 p.m.

1 stop9h 18m

C$ 483

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 12/9

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 21/9

7:45 p.m.-10:35 p.m.

Nonstop3h 50m

C$ 497

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 26/8

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Wed 2/9

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 507

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 12/9

11:05 a.m.-9:38 p.m.

2 stops9h 33m

Chicago O'Hare Intl

Sat 19/9

7:00 a.m.-1:10 p.m.

1 stop7h 10m

C$ 510

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 26/8

8:00 a.m.-8:21 p.m.

1 stop11h 21m

Chicago O'Hare Intl

Wed 2/9

8:40 a.m.-6:30 p.m.

1 stop10h 50m

C$ 517
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/10

12:30 p.m.-5:05 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 5/10

8:40 a.m.-11:28 a.m.

Nonstop3h 48m

C$ 562

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 11/9

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 11/9

3:45 p.m.-10:57 p.m.

1 stop8h 12m

C$ 595

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 24/12

7:15 a.m.-8:34 p.m.

2 stops13h 19m

Chicago O'Hare Intl

Fri 1/1

8:55 a.m.-9:54 p.m.

2 stops12h 59m

C$ 615

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

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?

The best time to book flights from Calgary to Chicago O'Hare Intl Airport is 44 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, November is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 352). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 545). 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 August 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?

Airfare is below average for this route at the moment.

Calgary to Chicago O'Hare Intl Airport flights typically cost between C$ 374 and C$ 595 in September.
The cheapest round-trip price found within the last 5 days was C$ 293 on WestJet (25 Sep-29 Sep).

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 August 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
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
Delta
7.8
Good
8,492 reviews
Delta
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
United Airlines
7.4
Good
10,062 reviews
Delta
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
WestJet
7.2
Good
3,423 reviews
Delta
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
American Airlines
7.1
Good
11,845 reviews
Delta
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
Air Canada
7.1
Good
11,419 reviews
Delta
7.8
Good
8,492 reviews
Check prices

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,

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 8 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 33m. United Airlines provides one of the quickest options available for as low as C$ 331. 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$ 123. Other airlines that can offer you cheap pricing are Delta, from C$ 143, and WestJet, from C$ 187. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 70% 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$ 138. Air Canada flights start at C$ 152 while deals on American Airlines start at C$ 170 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: Qatar Airways (81%), Air Canada (81%), United Airlines (81%).

  • 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$ 2,905, our data indicates the cheapest price to be C$ 264. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 321.

  • 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, November is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 352). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 545). 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
Northbrook
Evanston
Des Plaines
Downers Grove
Elk Grove Village
Racine
Rockford
Naperville
Schaumburg

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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
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 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 123AverageC$ 434FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 143AverageC$ 387FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 187AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 189AverageC$ 531FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 198AverageC$ 454FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

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

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

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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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