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Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 167

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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
12 Jul — 19 Jul1
1 adult

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 Friday or Thursday and return on a Monday

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 7 July 2025.

Round-trip from

C$ 195

One-way from

C$ 167

Popular in

December

Cheapest in

May

Average price

C$ 429

Good round-trip deal

C$ 504 or less

Good one-way deal

C$ 229 or less
WestJet
  • WestJet
  • 25/9-29/9
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
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WestJet
  • WestJet
  • 5/8
  • Nonstop
  • 3h 29m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 23% potential increase in price (C$ 157 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 34 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 7 July 2025.

Thu 25/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Mon 29/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 5/7C$ 195
Sat 22/1112:30 p.m.YYC - ORD
Nonstop3h 20mUnited Airlines
Sun 23/119:00 a.m.ORD - YYC
Nonstop3h 54mUnited Airlines
Deal found 7/7C$ 232
Thu 25/96:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Mon 29/910:05 p.m.ORD - YYC
1 stop14h 45mAmerican Airlines
Deal found 5/7C$ 274
Tue 19/81:05 a.m.YYC - ORD
1 stop7h 47mMultiple Airlines
Wed 27/85:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 6/7C$ 276
Tue 16/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Fri 19/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Deal found 7/7C$ 284
Wed 6/86:45 a.m.YYC - ORD
1 stop9h 04mDelta
Tue 12/88:25 a.m.ORD - YYC
2 stops15h 32mDelta
Deal found 6/7C$ 321

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 7 July 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

Thu 25/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Mon 29/9

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 22/11

12:30 p.m.-4:50 p.m.

Nonstop3h 20m

Chicago O'Hare Intl

Sun 23/11

9:00 a.m.-11:54 a.m.

Nonstop3h 54m

C$ 232

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 25/9

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Mon 29/9

10:05 p.m.-11:50 a.m.

1 stop14h 45m

C$ 274

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 19/8

1:05 a.m.-9:52 a.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 27/8

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 276

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 16/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

Chicago O'Hare Intl

Fri 19/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

C$ 284

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 6/8

6:45 a.m.-4:49 p.m.

1 stop9h 04m

Chicago O'Hare Intl

Tue 12/8

8:25 a.m.-10:57 p.m.

2 stops15h 32m

C$ 321

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 5/8

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

C$ 167

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 16/9

6:15 a.m.-10:42 p.m.

1 stop15h 27m

C$ 168

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 13/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 171

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 17/9

6:45 a.m.-8:01 p.m.

1 stop12h 16m

C$ 184

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 13 results
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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 27 June 2025.

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, January is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Calgary to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 352). 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 7 July 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 67% on flights from Calgary to Chicago O'Hare Intl Airport by exploring options for tickets in the evening.

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 7 July 2025.

The most flights from YYC to ORD are scheduled on a Sunday (15 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 7 July 2025.
See what other customers who have flown with Alaska Airlines,Delta, andUnited Airlines 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.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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
7,962 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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
8,844 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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
2,920 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Overall

8.0

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.8

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 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 12 outbound flights to Chicago O'Hare Intl per day. 5 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?

    Cheapflights users have booked flights from Calgary to Chicago O'Hare Intl Airport round-trip from C$ 195. Other airlines that can offer you cheap pricing are United Airlines, from C$ 232, and American Airlines, from C$ 274. 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?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 167. United Airlines flights start at C$ 168 while deals on Air Canada start at C$ 171 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: Avianca (93%), Envoy Air (85%), 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 C$ 2,404, our data indicates the cheapest price to be C$ 165. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 250.

  • 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, January is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Calgary to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 352). 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 Calgary?

Book flights to Calgary if you plan to visit one of these locations
Elk Grove Village
Evanston
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Bolingbrook
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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
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Fort McMurray to O'Hare Intl flights
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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 7 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 148AverageC$ 337FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 169AverageC$ 419FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 175AverageC$ 270FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 184AverageC$ 366FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 249AverageC$ 548FlexibilityNo cancel feeOn-time69%
Search United 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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