What’s the cheapest layover airport for flights from Calgary to Chicago O'Hare Intl Airport?

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 256.

Which airport typically offers the quickest layover for flights from Calgary to Chicago O'Hare Intl Airport?

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 53m.

What’s the top layover airport for flights from Calgary to Chicago O'Hare Intl Airport?

Toronto (YYZ) – chosen by Cheapflights users on 58% of one-stop itineraries from Calgary to Chicago O'Hare Intl Airport on Cheapflights.

What’s the fastest layover option from Calgary to Chicago O'Hare Intl Airport?

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 42m.

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 28m. WestJet provides one of the quickest options available for as low as C$ 216. Airlines will cover a distance of 2223 km. Generally, flights for this route are direct.

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$ 149. Other airlines that can offer you cheap pricing are WestJet, from C$ 176, and Delta, from C$ 184. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 60% less than the average price by searching for these airlines.

What is the cheapest day to fly from Calgary to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Calgary to Chicago O'Hare Intl Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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

The most flights from YYC to ORD are scheduled on a Tuesday (14 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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$ 1,370, our data indicates the cheapest price to be C$ 136. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 238.

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 (80%), Air Canada (79%), United Airlines (79%).

What are the most popular airlines that fly from Calgary to Chicago O'Hare Intl Airport?

American Airlines, Air Canada and Delta are the most popular airlines when flying from Calgary to Chicago O'Hare Intl Airport.

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 11 outbound flights to Chicago O'Hare Intl per day. 5 airlines have flights to Chicago O'Hare Intl from Calgary on a regular basis.

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.

C$ 152+ Cheap Flights from Calgary to Chicago O'Hare Intl Airport

Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in May or April, booked 81 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Calgary to O'Hare Intl

Round-trip from	C$ 216
One-way from	C$ 152
Popular in	December
Cheapest in	May
Average price	C$ 327
Good round-trip deal	C$ 473 or less
Good one-way deal	C$ 289 or less

WestJet
3/10-5/10
Nonstop
7h 17m total
Calgary to Chicago

Search Deals

United Airlines
18/11
Nonstop
3h 33m total
Calgary to Chicago

Search Deals

Highest demand for flights based on searches. 20% potential increase in price (C$ 130 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease (C$ 34 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2025

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

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 16 September 2025.

Fri 3/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 5/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 15/9C$ 216

Fri 17/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 221

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 19/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 225

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 227

Thu 11/1212:35 p.m.YYC - ORD

Nonstop3h 35mUnited Airlines

Mon 15/127:10 a.m.ORD - YYC

1 stop15h 43mUnited Airlines

Deal found 15/9C$ 238

Sat 18/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 243

Fri 31/1011:40 p.m.YYC - ORD

1 stop14h 30mMultiple Airlines

Fri 7/112:20 p.m.ORD - YYC

Nonstop3h 55mMultiple Airlines

Deal found 16/9C$ 250

Mon 27/1011:15 a.m.YYC - ORD

1 stop11h 29mMultiple Airlines

Fri 31/102:20 p.m.ORD - YYC

Nonstop3h 55mMultiple Airlines

Deal found 14/9C$ 262

Fri 17/1012:38 p.m.YYC - ORD

Nonstop3h 32mUnited Airlines

Tue 21/107:10 a.m.ORD - YYC

1 stop7h 43mUnited Airlines

Deal found 16/9C$ 272

Sat 11/106:15 a.m.YYC - ORD

1 stop14h 15mUnited Airlines

Sat 18/105:01 a.m.ORD - YYC

1 stop9h 52mUnited Airlines

Deal found 16/9C$ 279

Sat 4/101:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Tue 7/103:50 p.m.ORD - YYC

1 stop8h 32mAir Canada

Deal found 14/9C$ 280

Best flights from Calgary to O'Hare Intl
Discover carefully curated flight deals from Calgary to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 September 2025.

Fri 3/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 5/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 15/9C$ 216

Thu 11/1212:35 p.m.YYC - ORD

Nonstop3h 35mUnited Airlines

Mon 15/127:10 a.m.ORD - YYC

1 stop15h 43mUnited Airlines

Deal found 15/9C$ 238

Thu 11/127:35 a.m.YYC - ORD

1 stop10h 10mDelta

Mon 15/121:38 p.m.ORD - YYC

1 stop10h 35mDelta

Deal found 14/9C$ 308

Fri 28/116:15 a.m.YYC - ORD

1 stop16h 44mMultiple Airlines

Tue 2/122:00 p.m.ORD - YYC

1 stop7h 39mMultiple Airlines

Deal found 15/9C$ 309

Fri 2/19:00 a.m.YYC - ORD

Nonstop3h 35mWestJet

Mon 5/12:20 p.m.ORD - YYC

Nonstop3h 55mWestJet

Deal found 15/9C$ 240

Sat 11/106:15 a.m.YYC - ORD

1 stop14h 15mUnited Airlines

Sat 18/105:01 a.m.ORD - YYC

1 stop9h 52mUnited Airlines

Deal found 16/9C$ 279

Mon 10/117:45 a.m.YYC - ORD

1 stop10h 00mDelta

Thu 13/111:38 p.m.ORD - YYC

1 stop10h 32mDelta

Deal found 15/9C$ 308

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mMultiple Airlines

Mon 20/109:54 p.m.ORD - YYC

1 stop15h 01mMultiple Airlines

Deal found 15/9C$ 320

Thu 4/127:35 a.m.YYC - ORD

1 stop10h 10mDelta

Sun 7/126:00 a.m.ORD - YYC

1 stop8h 55mDelta

Deal found 13/9C$ 308

Tue 21/107:45 a.m.YYC - ORD

1 stop9h 56mDelta

Thu 23/106:45 a.m.ORD - YYC

2 stops15h 02mDelta

Deal found 15/9C$ 308

Sat 18/106:45 a.m.YYC - ORD

1 stop7h 15mDelta

Thu 23/108:57 a.m.ORD - YYC

1 stop5h 57mDelta

Deal found 16/9C$ 309

Direct flights from Calgary to O'Hare Intl
Explore direct flight options from Calgary to O'Hare Intl based on user searches, and compare prices and availability for your desired travel dates. Data last updated 16 September 2025.

Fri 3/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 5/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 15/9C$ 216

Fri 17/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 221

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 19/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 225

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 227

Mon 2/29:00 a.m.YYC - ORD

Nonstop3h 35mWestJet

Mon 9/22:20 p.m.ORD - YYC

Nonstop3h 55mWestJet

Deal found 14/9C$ 238

Fri 2/19:00 a.m.YYC - ORD

Nonstop3h 35mWestJet

Mon 5/12:20 p.m.ORD - YYC

Nonstop3h 55mWestJet

Deal found 15/9C$ 240

Sat 18/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 243

Fri 17/1012:38 p.m.YYC - ORD

Nonstop3h 32mUnited Airlines

Tue 21/108:47 a.m.ORD - YYC

Nonstop3h 51mUnited Airlines

Deal found 16/9C$ 272

Fri 31/1012:37 p.m.YYC - ORD

Nonstop3h 33mMultiple Airlines

Fri 7/112:20 p.m.ORD - YYC

Nonstop3h 55mMultiple Airlines

Deal found 16/9C$ 285

Sun 19/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 305

Sun 5/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 12/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 14/9C$ 344

Last-minute flights from Calgary to O'Hare Intl
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated 16 September 2025 and is based on user searches.

Fri 3/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 5/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 15/9C$ 216

Sat 4/101:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Tue 7/103:50 p.m.ORD - YYC

1 stop8h 32mAir Canada

Deal found 14/9C$ 280

Sat 11/106:15 a.m.YYC - ORD

1 stop14h 15mUnited Airlines

Sat 18/105:01 a.m.ORD - YYC

1 stop9h 52mUnited Airlines

Deal found 16/9C$ 279

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Sun 19/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 225

Thu 16/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 227

Fri 17/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 221

Fri 17/1012:38 p.m.YYC - ORD

Nonstop3h 32mUnited Airlines

Sun 19/105:01 a.m.ORD - YYC

1 stop9h 52mUnited Airlines

Deal found 16/9C$ 272

Sat 18/1012:15 p.m.YYC - ORD

Nonstop3h 28mWestJet

Thu 23/105:30 p.m.ORD - YYC

Nonstop3h 49mWestJet

Deal found 16/9C$ 243

Sun 26/109:00 a.m.YYC - ORD

1 stop8h 55mAir Canada

Sat 1/113:55 p.m.ORD - YYC

1 stop9h 19mAir Canada

Deal found 16/9C$ 286

Mon 27/1011:15 a.m.YYC - ORD

1 stop11h 29mMultiple Airlines

Fri 31/102:20 p.m.ORD - YYC

Nonstop3h 55mMultiple Airlines

Deal found 14/9C$ 262

Fri 31/1011:40 p.m.YYC - ORD

1 stop14h 30mMultiple Airlines

Fri 7/112:20 p.m.ORD - YYC

Nonstop3h 55mMultiple Airlines

Deal found 16/9C$ 250

One-way flights from Calgary to O'Hare Intl
Search for one-way flight options from Calgary to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 16 September 2025.

Tue 18/1112:37 p.m.YYC - ORD

Nonstop3h 33mUnited Airlines

Deal found 16/9C$ 152

Tue 7/101:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Deal found 14/9C$ 156

Tue 11/115:45 a.m.YYC - ORD

1 stop8h 25mAir Canada

Deal found 14/9C$ 159

Sat 11/101:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Deal found 15/9C$ 160

Wed 29/101:29 p.m.YYC - ORD

Nonstop3h 25mAmerican Airlines

Deal found 14/9C$ 163

Fri 9/11:40 p.m.YYC - ORD

Nonstop3h 40mAmerican Airlines

Deal found 15/9C$ 164

Thu 16/101:10 a.m.YYC - ORD

1 stop6h 59mAir Canada

Deal found 15/9C$ 169

Sat 11/106:15 a.m.YYC - ORD

1 stop14h 15mUnited Airlines

Deal found 16/9C$ 170

Wed 1/101:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Deal found 14/9C$ 171

Wed 29/105:45 a.m.YYC - ORD

1 stop8h 25mAir Canada

Deal found 14/9C$ 173

Tue 30/91:10 a.m.YYC - ORD

1 stop7h 41mAir Canada

Deal found 15/9C$ 175

Cheapflights Fare Finder

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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/10

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

Nonstop3h 28m

Chicago O'Hare Intl

Sun 5/10

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

Nonstop3h 49m

C$ 216

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 5/1

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 240

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 11/10

6:15 a.m.-9:30 p.m.

1 stop14h 15m

Chicago O'Hare Intl

Sat 18/10

5:01 a.m.-1:53 p.m.

1 stop9h 52m

C$ 279

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

7:35 a.m.-6:45 p.m.

1 stop10h 10m

Chicago O'Hare Intl

Mon 15/12

1:38 p.m.-11:13 p.m.

1 stop10h 35m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 10/11

7:45 a.m.-6:45 p.m.

1 stop10h 00m

Chicago O'Hare Intl

Thu 13/11

1:38 p.m.-11:10 p.m.

1 stop10h 32m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/12

7:35 a.m.-6:45 p.m.

1 stop10h 10m

Chicago O'Hare Intl

Sun 7/12

6:00 a.m.-1:55 p.m.

1 stop8h 55m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 21/10

7:45 a.m.-6:41 p.m.

1 stop9h 56m

Chicago O'Hare Intl

Thu 23/10

6:45 a.m.-8:47 p.m.

2 stops15h 02m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 28/11

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Tue 2/12

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 309

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 18/10

6:45 a.m.-3:00 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Thu 23/10

8:57 a.m.-1:54 p.m.

1 stop5h 57m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 22 results

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

Prices

Airlines

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 81 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$ 348). 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?

Unlike at noon, when flights are generally more expensive, you can save up to 68% on flights from Calgary to Chicago O'Hare Intl Airport by exploring options for tickets in the evening.

Reviews of airlines servicing O'Hare Intl

See what other customers who have flown with Delta,United Airlines, andAmerican 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.

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Delta

8.0

Very good

7,957 reviews

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

United Airlines

7.4

Good

8,924 reviews

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

WestJet

7.2

Good

3,093 reviews

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Air Canada

7.1

Good

10,000 reviews

Delta

8.0

Very good

7,957 reviews

Check prices

Reviews

1 / 20

6.0

Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

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 11 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 28m. WestJet provides one of the quickest options available for as low as C$ 216. Airlines will cover a distance of 2223 km. Generally, flights for this route are direct.
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$ 149. Other airlines that can offer you cheap pricing are WestJet, from C$ 176, and Delta, from C$ 184. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 60% less than the average price by searching for these airlines.
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 (80%), Air Canada (79%), United Airlines (79%).
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$ 1,370, our data indicates the cheapest price to be C$ 136. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 238.
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$ 348). 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

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Downers Grove

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Browse thousands of different options on Cheapflights for your next trip

Top 5 airlines flying from Calgary to O'Hare Intl

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 149	AverageC$ 342	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
WestJet	CheapestC$ 176	AverageC$ 252	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Delta	CheapestC$ 184	AverageC$ 345	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights
American Airlines	CheapestC$ 185	AverageC$ 423	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
United Airlines	CheapestC$ 251	AverageC$ 527	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

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Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 152

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 18/11. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in May or April, booked 81 days in advance, depart on a Friday or Thursday and return on a Wednesday

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Find flight deals from Calgary to O'Hare Intl

Cheapest flights from Calgary to O'Hare IntlExplore 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 16 September 2025.

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 16 September 2025.

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

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Cheapflights Insights

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

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

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Reviews of airlines servicing O'Hare Intl

See what other customers who have flown with Delta,United Airlines, andAmerican 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.

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.

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

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

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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 16 September 2025.