Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 232
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 13/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
2 Dec — 9 Dec1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in May or February, booked 60 days in advance, depart on a Friday or Thursday and return on a Monday
Cheap flight deals from Calgary to O'Hare Intl
Enter your travel dates to find the best prices.
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One-way
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 November 2026.
Fri 4/129:07 a.m. -
1 stop8h 42m
Mon 7/126:47 p.m. -
1 stop26h 50m
Deal found 31/10C$ 422
Sat 21/118:45 a.m. -
1 stop6h 10m
Wed 25/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 425
Mon 16/119:09 a.m. -
2 stops28h 00m
Wed 18/117:00 a.m. -
1 stop14h 39m
Deal found 2/11C$ 435
Fri 4/129:07 a.m. -
1 stop7h 24m
Sun 6/126:00 a.m. -
1 stop15h 37m
Deal found 2/11C$ 439
Thu 3/121:37 p.m. -
Nonstop3h 33m
Tue 8/1212:29 p.m. -
1 stop10h 24m
Deal found 1/11C$ 446
Thu 3/127:25 a.m. -
2 stops11h 01m
Tue 8/1212:34 p.m. -
2 stops11h 47m
Deal found 1/11C$ 447
Tue 22/128:45 a.m. -
1 stop9h 44m
Tue 9/29:59 a.m. -
2 stops14h 24m
Deal found 30/10C$ 448
Fri 11/121:37 p.m. -
Nonstop3h 33m
Sun 13/124:30 p.m. -
1 stop7h 51m
Deal found 31/10C$ 451
Tue 1/128:45 a.m. -
1 stop7h 58m
Wed 9/1212:34 p.m. -
2 stops11h 47m
Deal found 29/10C$ 453
Thu 12/111:35 p.m. -
1 stop8h 12m
Tue 24/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 455
Mon 16/119:09 a.m. -
2 stops28h 00m
Thu 19/117:00 a.m. -
1 stop14h 30m
Deal found 30/10C$ 457
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 2 November 2026.
Fri 4/129:07 a.m. -
1 stop8h 42m
Mon 7/126:47 p.m. -
1 stop26h 50m
Deal found 31/10C$ 422
Sat 23/17:15 a.m. -
2 stops14h 21m
Mon 25/19:50 a.m. -
2 stops12h 11m
Deal found 1/11C$ 425
Thu 3/121:37 p.m. -
Nonstop3h 33m
Tue 8/1212:29 p.m. -
1 stop10h 24m
Deal found 1/11C$ 446
Thu 1/47:45 a.m. -
1 stop8h 04m
Tue 6/41:55 p.m. -
1 stop10h 18m
Deal found 1/11C$ 425
Thu 10/121:37 p.m. -
Nonstop3h 33m
Sat 12/127:00 a.m. -
1 stop15h 53m
Deal found 1/11C$ 461
Fri 4/129:07 a.m. -
1 stop7h 24m
Tue 8/126:00 a.m. -
1 stop15h 37m
Deal found 29/10C$ 465
Thu 3/127:25 a.m. -
2 stops12h 50m
Tue 8/122:04 p.m. -
1 stop10h 17m
Deal found 1/11C$ 447
Fri 4/123:06 p.m. -
1 stop8h 53m
Tue 8/128:40 a.m. -
Nonstop3h 55m
Deal found 29/10C$ 474
Fri 2/46:25 a.m. -
1 stop10h 32m
Tue 6/41:55 p.m. -
1 stop10h 18m
Deal found 1/11C$ 461
Thu 17/121:37 p.m. -
Nonstop3h 33m
Mon 21/126:50 a.m. -
1 stop12h 07m
Deal found 30/10C$ 482
Sun 15/117:25 a.m. -
1 stop10h 40m
Tue 17/112:03 p.m. -
1 stop10h 14m
Deal found 30/10C$ 490
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 2 November 2026.
Thu 21/11:37 p.m. -
Nonstop3h 33m
Sun 24/18:40 a.m. -
Nonstop3h 55m
Deal found 31/10C$ 486
Wed 24/21:39 p.m. -
Nonstop3h 31m
Mon 1/38:40 a.m. -
Nonstop3h 57m
Deal found 31/10C$ 490
Thu 3/121:37 p.m. -
Nonstop3h 33m
Tue 8/128:40 a.m. -
Nonstop3h 55m
Deal found 1/11C$ 545
Fri 27/111:37 p.m. -
Nonstop3h 33m
Fri 4/128:40 a.m. -
Nonstop3h 55m
Deal found 30/10C$ 546
Fri 26/32:29 p.m. -
Nonstop3h 56m
Sat 3/410:51 a.m. -
Nonstop3h 53m
Deal found 29/10C$ 564
Thu 1/42:29 p.m. -
Nonstop3h 56m
Sun 4/410:51 a.m. -
Nonstop3h 53m
Deal found 28/10C$ 569
Thu 25/23:29 p.m. -
Nonstop3h 56m
Sun 28/210:51 a.m. -
Nonstop3h 53m
Deal found 30/10C$ 573
Last-minute flights from Calgary to O'Hare Intl
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated 2 November 2026 and is based on user searches.
Thu 12/111:35 p.m. -
1 stop8h 12m
Tue 24/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 455
Mon 16/119:09 a.m. -
2 stops28h 00m
Wed 18/117:00 a.m. -
1 stop14h 39m
Deal found 2/11C$ 435
Mon 16/119:09 a.m. -
2 stops28h 00m
Thu 19/117:00 a.m. -
1 stop14h 30m
Deal found 30/10C$ 457
Fri 20/117:00 a.m. -
1 stop8h 38m
Mon 23/113:50 p.m. -
1 stop9h 00m
Deal found 1/11C$ 462
Sat 21/118:45 a.m. -
1 stop6h 10m
Wed 25/112:03 p.m. -
1 stop10h 14m
Deal found 1/11C$ 425
Mon 23/112:20 p.m. -
1 stop7h 13m
Tue 1/122:04 p.m. -
1 stop10h 17m
Deal found 28/10C$ 468
Mon 23/111:37 p.m. -
Nonstop3h 33m
Tue 1/128:45 a.m. -
1 stop9h 13m
Deal found 28/10C$ 471
Wed 25/111:20 a.m. -
1 stop8h 03m
Mon 30/114:30 p.m. -
1 stop7h 36m
Deal found 1/11C$ 469
Wed 25/113:06 p.m. -
1 stop7h 40m
Mon 30/114:30 p.m. -
1 stop7h 36m
Deal found 31/10C$ 481
Thu 26/111:37 p.m. -
Nonstop3h 33m
Mon 30/112:30 p.m. -
1 stop8h 23m
Deal found 31/10C$ 461
Thu 26/111:37 p.m. -
Nonstop3h 33m
Mon 30/114:30 p.m. -
1 stop7h 36m
Deal found 31/10C$ 472
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 2 November 2026.
Sun 13/122:55 p.m. -
1 stop19h 37m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/10C$ 232
Fri 15/17:15 a.m. -
1 stop10h 54m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 2/11C$ 251
Thu 10/127:25 a.m. -
1 stop10h 41m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 31/10C$ 253
Fri 25/128:45 a.m. -
2 stops11h 33m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 29/10C$ 258
Mon 23/111:45 a.m. -
1 stop9h 22m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/11C$ 264
Fri 25/129:03 a.m. -
1 stop8h 56m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 29/10C$ 268
Thu 12/111:20 a.m. -
1 stop8h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/10C$ 270
Tue 29/127:59 p.m. -
1 stop13h 35m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 1/11C$ 272
Wed 25/113:06 p.m. -
1 stop7h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 31/10C$ 274
Wed 25/111:20 a.m. -
1 stop8h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 31/10C$ 278
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 November 2026.
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 7,457,451 searches. Data last updated 2 November 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 Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 15/1
7:15 a.m.-8:32 p.m.
2 stops13h 17m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 251
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Tue 9/3
8:45 a.m.-10:20 p.m.
2 stops13h 35m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 251
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sun 6/12
7:25 a.m.-6:06 p.m.
1 stop10h 41m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 251
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 30/11
7:25 a.m.-6:05 p.m.
1 stop10h 40m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 253
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 10/12
7:25 a.m.-6:06 p.m.
1 stop10h 41m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 253
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 12/11
1:20 a.m.-9:23 a.m.
1 stop8h 03m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 270
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 9/11
7:25 a.m.-6:05 p.m.
1 stop10h 40m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 292
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 17/12
1:37 p.m.-5:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 312
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 18/12
1:37 p.m.-5:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 344
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 4/12
9:07 a.m.-5:49 p.m.
1 stop8h 42m
Chicago O'Hare Intl
Mon 7/12
6:47 p.m.-9:37 p.m.
1 stop26h 50m
C$ 422
Flights are sorted by cheapest round-trip flights first.
Deals found on 2/11
Showing 1-10 of 20 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.
YYC-ORD
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
More
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 59 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, May 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 October is currently the most expensive (average of C$ 577). 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 November 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 typical for this route at the moment.
Calgary to Chicago O'Hare Intl Airport flights typically cost between C$ 374 and C$ 699 in December.The cheapest round-trip price found within the last 5 days was C$ 422 on Alaska Airlines (4 Dec-7 Dec).
What’s the top layover airport for flights from Calgary to Chicago O'Hare Intl Airport?
Share of one-stop round-trip flights from Calgary to Chicago O'Hare Intl Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.
Ottawa (YOW) – chosen by Cheapflights users on 50% of one-stop itineraries from Calgary to Chicago O'Hare Intl Airport on Cheapflights.
What’s the cheapest layover airport for flights from Calgary to Chicago O'Hare Intl Airport?
Average round-trip fare for 1-stop flights from Calgary to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 433.
What’s the fastest layover option from Calgary to Chicago O'Hare Intl Airport?
Shortest average travel time for 1-stop one-way flights from Calgary to Chicago O'Hare Intl Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 23m.
Which airport typically offers the quickest layover for flights from Calgary to Chicago O'Hare Intl Airport?
Average layover duration for 1-stop one-way flights from Calgary to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 2h 26m.
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 November 2026.
See what other customers who have flown with Porter Airlines,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.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
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 3 outbound flights to Chicago O'Hare Intl per day. 6 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. Alaska Airlines provides one of the quickest options available for as low as C$ 446. 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$ 143. Other airlines that can offer you cheap pricing are Air Canada, from C$ 186, and United Airlines, from C$ 189. 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$ 145. Air Canada flights start at C$ 152 while deals on American Airlines start at C$ 169 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 (82%), Scandinavian Airlines (77%), Air Canada (75%).
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$ 1,841, our data indicates the cheapest price to be C$ 260. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 425.
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, May 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 October is currently the most expensive (average of C$ 577). 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.
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 2 November 2026.
Discover the top 6 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 7,457,451 searches. Data last updated 2 November 2026.
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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