Cheap flights from Calgary to Chicago O'Hare Intl Airport from C$ 230
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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
1 Oct — 8 Oct1
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 November or May, booked 66 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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Best
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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 1 September 2026.
Sat 14/111:37 p.m. -
Nonstop2h 33m
Mon 23/114:30 p.m. -
1 stop8h 36m
Deal found 1/9C$ 354
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Mon 2/117:00 a.m. -
1 stop16h 53m
Deal found 28/8C$ 355
Sat 10/101:00 a.m. -
1 stop8h 17m
Fri 16/103:45 p.m. -
1 stop8h 12m
Deal found 1/9C$ 358
Tue 6/1012:00 p.m. -
Nonstop3h 40m
Fri 9/105:30 p.m. -
Nonstop3h 55m
Deal found 30/8C$ 361
Sun 22/117:00 a.m. -
1 stop12h 29m
Sat 28/118:40 a.m. -
Nonstop4h 55m
Deal found 30/8C$ 364
Fri 11/912:33 p.m. -
Nonstop3h 32m
Mon 14/95:55 a.m. -
1 stop8h 58m
Deal found 1/9C$ 368
Fri 2/1012:00 p.m. -
Nonstop3h 40m
Mon 5/105:30 p.m. -
Nonstop3h 55m
Deal found 28/8C$ 369
Tue 10/111:37 p.m. -
Nonstop2h 33m
Thu 12/118:40 a.m. -
Nonstop4h 55m
Deal found 31/8C$ 375
Sun 22/117:00 a.m. -
1 stop7h 38m
Sat 28/114:30 p.m. -
1 stop8h 36m
Deal found 30/8C$ 379
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 1 September 2026.
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Mon 2/117:00 a.m. -
1 stop16h 53m
Deal found 28/8C$ 355
Fri 30/101:40 p.m. -
2 stops9h 17m
Mon 2/1112:30 p.m. -
2 stops12h 40m
Deal found 31/8C$ 383
Thu 1/106:00 a.m. -
1 stop14h 52m
Mon 5/106:00 a.m. -
1 stop16h 48m
Deal found 30/8C$ 408
Wed 16/96:35 a.m. -
1 stop9h 24m
Sat 19/912:29 p.m. -
1 stop9h 13m
Deal found 31/8C$ 444
Wed 24/23:06 p.m. -
1 stop5h 07m
Mon 1/36:00 a.m. -
1 stop14h 18m
Deal found 1/9C$ 414
Thu 24/96:35 a.m. -
1 stop7h 30m
Thu 1/102:05 p.m. -
1 stop10h 01m
Deal found 27/8C$ 464
Wed 16/912:33 p.m. -
Nonstop3h 32m
Sat 19/97:45 p.m. -
Nonstop3h 50m
Deal found 31/8C$ 436
Thu 1/108:45 a.m. -
1 stop8h 16m
Sun 4/105:30 p.m. -
Nonstop3h 55m
Deal found 27/8C$ 500
Fri 27/113:06 p.m. -
1 stop7h 53m
Wed 2/128:40 a.m. -
Nonstop4h 55m
Deal found 30/8C$ 466
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 1 September 2026.
Tue 6/1012:00 p.m. -
Nonstop3h 40m
Fri 9/105:30 p.m. -
Nonstop3h 55m
Deal found 30/8C$ 361
Fri 2/1012:00 p.m. -
Nonstop3h 40m
Mon 5/105:30 p.m. -
Nonstop3h 55m
Deal found 28/8C$ 369
Tue 9/21:37 p.m. -
Nonstop2h 33m
Tue 2/39:00 a.m. -
Nonstop4h 54m
Deal found 1/9C$ 371
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Mon 2/118:40 a.m. -
Nonstop4h 55m
Deal found 30/8C$ 373
Tue 10/111:37 p.m. -
Nonstop2h 33m
Thu 12/118:40 a.m. -
Nonstop4h 55m
Deal found 31/8C$ 375
Fri 11/97:00 a.m. -
Nonstop3h 29m
Mon 14/98:30 p.m. -
Nonstop3h 59m
Deal found 1/9C$ 386
Thu 22/1012:30 p.m. -
Nonstop3h 35m
Thu 29/108:40 a.m. -
Nonstop3h 55m
Deal found 30/8C$ 390
Thu 12/111:37 p.m. -
Nonstop2h 33m
Tue 17/118:40 a.m. -
Nonstop4h 55m
Deal found 28/8C$ 400
Tue 15/97:00 a.m. -
Nonstop3h 29m
Tue 22/98:30 p.m. -
Nonstop3h 59m
Deal found 31/8C$ 405
Sun 18/1012:00 p.m. -
Nonstop3h 40m
Thu 22/105:30 p.m. -
Nonstop3h 55m
Deal found 30/8C$ 415
Fri 25/97:00 a.m. -
Nonstop3h 29m
Tue 29/95:30 p.m. -
Nonstop3h 55m
Deal found 27/8C$ 422
Last-minute flights from Calgary to O'Hare Intl
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated 1 September 2026 and is based on user searches.
Fri 11/912:33 p.m. -
Nonstop3h 32m
Mon 14/95:55 a.m. -
1 stop8h 58m
Deal found 1/9C$ 368
Fri 11/97:00 a.m. -
Nonstop3h 29m
Mon 14/98:30 p.m. -
Nonstop3h 59m
Deal found 1/9C$ 386
Wed 30/912:50 a.m. -
1 stop7h 10m
Mon 5/105:35 p.m. -
1 stop8h 42m
Deal found 27/8C$ 389
Fri 2/1012:00 p.m. -
Nonstop3h 40m
Mon 5/105:30 p.m. -
Nonstop3h 55m
Deal found 28/8C$ 369
Tue 6/1012:00 p.m. -
Nonstop3h 40m
Fri 9/105:30 p.m. -
Nonstop3h 55m
Deal found 30/8C$ 361
Sat 10/101:00 a.m. -
1 stop8h 17m
Fri 16/103:45 p.m. -
1 stop8h 12m
Deal found 1/9C$ 358
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Mon 2/117:00 a.m. -
1 stop16h 53m
Deal found 28/8C$ 355
Fri 30/101:40 p.m. -
2 stops9h 17m
Mon 2/1112:30 p.m. -
2 stops12h 40m
Deal found 31/8C$ 383
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 1 September 2026.
Fri 30/101:40 p.m. -
2 stops9h 17m
Deal found 31/8C$ 230
Thu 25/21:30 p.m. -
Nonstop2h 20m
Deal found 28/8C$ 232
Mon 5/101:00 a.m. -
1 stop8h 17m
Deal found 31/8C$ 233
Fri 30/106:00 a.m. -
1 stop8h 38m
Deal found 31/8C$ 235
Tue 29/96:30 a.m. -
2 stops12h 42m
Deal found 30/8C$ 236
Thu 26/117:00 a.m. -
1 stop7h 38m
Deal found 28/8C$ 237
Fri 18/97:00 a.m. -
Nonstop3h 29m
Deal found 31/8C$ 239
Mon 5/1011:55 p.m. -
1 stop8h 05m
Deal found 31/8C$ 240
Thu 1/106:00 a.m. -
1 stop14h 18m
Deal found 30/8C$ 243
Thu 29/109:10 p.m. -
2 stops11h 13m
Deal found 28/8C$ 244
Thu 1/106:35 a.m. -
2 stops10h 51m
Deal found 31/8C$ 246
Fri 30/101:51 p.m. -
Nonstop3h 45m
Deal found 31/8C$ 247
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 1 September 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 1 September 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 30/10
12:37 p.m.-5:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Mon 2/11
7:00 a.m.-11:53 p.m.
1 stop16h 53m
C$ 355
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 30/10
1:40 p.m.-11:57 p.m.
2 stops9h 17m
Chicago O'Hare Intl
Mon 2/11
12:30 p.m.-1:10 a.m.
2 stops12h 40m
C$ 383
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 1/10
6:00 a.m.-9:52 p.m.
1 stop14h 52m
Chicago O'Hare Intl
Mon 5/10
6:00 a.m.-9:48 p.m.
1 stop16h 48m
C$ 408
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 24/2
3:06 p.m.-8:13 p.m.
1 stop5h 07m
Chicago O'Hare Intl
Mon 1/3
6:00 a.m.-8:18 p.m.
1 stop14h 18m
C$ 414
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 16/9
12:33 p.m.-5:05 p.m.
Nonstop3h 32m
Chicago O'Hare Intl
Sat 19/9
7:45 p.m.-10:35 p.m.
Nonstop3h 50m
C$ 436
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 16/9
6:35 a.m.-4:59 p.m.
1 stop9h 24m
Chicago O'Hare Intl
Sat 19/9
12:29 p.m.-8:42 p.m.
1 stop9h 13m
C$ 444
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 24/9
6:35 a.m.-3:05 p.m.
1 stop7h 30m
Chicago O'Hare Intl
Thu 1/10
2:05 p.m.-11:06 p.m.
1 stop10h 01m
C$ 464
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 27/11
3:06 p.m.-10:59 p.m.
1 stop7h 53m
Chicago O'Hare Intl
Wed 2/12
8:40 a.m.-1:35 p.m.
Nonstop4h 55m
C$ 466
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 1/10
8:45 a.m.-6:01 p.m.
1 stop8h 16m
Chicago O'Hare Intl
Sun 4/10
5:30 p.m.-8:25 p.m.
Nonstop3h 55m
C$ 500
Cheapest one-way
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sat 31/10
6:35 a.m.-4:26 p.m.
2 stops8h 51m
C$ 230
Flights are sorted by cheapest round-trip flights first.
Deals found on 31/8
Showing 1-10 of 20 resultsSorted by cheapest first
1
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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.
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
Airlines
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, November is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of C$ 343). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 548). 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 1 September 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$ 376 and C$ 515 in October.The cheapest round-trip price found within the last 5 days was C$ 355 on United Airlines (30 Oct-2 Nov).
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 1 September 2026.
The most flights from YYC to ORD are scheduled on a Friday (16 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (10 on average).
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 54% 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$ 430.
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 19m.
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 22m.
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 1 September 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.
Although I still enjoy flying Delta, the overall flying experience feels cheapened. But I guess that is true of most, if not all american carriers.
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 13 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$ 355. 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 Delta, from C$ 142, and United Airlines, 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$ 136. Air Canada flights start at C$ 151 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: 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$ 1,901, our data indicates the cheapest price to be C$ 287. The most popular route (Calgary - Chicago O'Hare Intl), is priced around C$ 341.
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$ 343). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of C$ 548). 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 1 September 2026.
Browse through other flights departing from Calgary. Flights are based on user searches made on Cheapflights and were last updated on 1 September 2026.
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 7,457,451 searches. Data last updated 1 September 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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