$172+ Cheap flights from Calgary (YYC) to O'Hare Intl (ORD)
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Sep 18 — Sep 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Calgary to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Calgary to Chicago O'Hare Intl are usually found in May or January, booked 66 days in advance, depart on a Friday or Sunday and return on a Friday
Cheap flight deals from Calgary to O'Hare Intl
Cheapest
Best
Last-minute
One-way
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 August 19, 2026.
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 August 19, 2026.
This Traveloka deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:55 pm -
1 stop8h 05m
Mon 10/55:30 pm -
Nonstop3h 55m
Deal found 8/14![Multiple Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:30 pm -
Nonstop2h 20m
Sun 12/69:00 am -
Nonstop4h 54m
Deal found 8/16![United Airlines logo]()
$246
This Air Canada deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop8h 38m
Mon 11/210:15 am -
1 stop10h 44m
Deal found 8/17![Air Canada logo]()
$248
This Trip.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:00 pm -
Nonstop3h 40m
Sun 9/65:30 pm -
Nonstop3h 55m
Deal found 8/17![WestJet logo]()
$249
This FlightHub deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:00 pm -
Nonstop3h 40m
Tue 9/155:30 pm -
Nonstop3h 55m
Deal found 8/13![WestJet logo]()
$252
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:00 pm -
Nonstop3h 40m
Sun 9/205:30 pm -
Nonstop3h 55m
Deal found 8/18![WestJet logo]()
$253
This Trip.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:00 pm -
Nonstop3h 40m
Mon 9/285:30 pm -
Nonstop3h 55m
Deal found 8/14![WestJet logo]()
$257
This Trip.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:00 pm -
Nonstop3h 40m
Mon 10/55:30 pm -
Nonstop3h 55m
Deal found 8/13![WestJet logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:06 pm -
1 stop7h 13m
Tue 12/89:00 am -
Nonstop4h 54m
Deal found 8/16![United Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:00 pm -
Nonstop3h 40m
Fri 9/255:30 pm -
Nonstop3h 55m
Deal found 8/13![WestJet logo]()
$263
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:30 am -
Nonstop3h 35m
Wed 10/288:40 am -
Nonstop3h 55m
Deal found 8/17![United Airlines logo]()
$265
Best flights from Calgary to O'Hare IntlDiscover 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 August 19, 2026.
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 August 19, 2026.
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:35 am -
1 stop10h 35m
Fri 10/3012:29 pm -
1 stop9h 11m
Deal found 8/14![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:30 am -
Nonstop3h 35m
Sat 8/298:44 am -
Nonstop3h 48m
Deal found 8/17![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:45 am -
1 stop9h 34m
Sun 9/66:00 am -
1 stop7h 55m
Deal found 8/13![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:45 am -
1 stop9h 34m
Wed 9/22:00 pm -
1 stop10h 04m
Deal found 8/14![Delta logo]()
$312
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:35 am -
1 stop10h 35m
Mon 11/28:29 am -
2 stops14h 11m
Deal found 8/15![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:45 am -
1 stop9h 34m
Sun 9/66:00 am -
1 stop7h 55m
Deal found 8/18![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2112:15 pm -
2 stops8h 19m
Tue 12/18:29 am -
2 stops13h 16m
Deal found 8/16![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:00 pm -
Nonstop3h 40m
Fri 9/115:30 pm -
Nonstop3h 55m
Deal found 8/13![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:00 pm -
Nonstop3h 40m
Fri 10/95:30 pm -
Nonstop3h 55m
Deal found 8/18![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:45 am -
1 stop9h 56m
Sat 9/512:29 pm -
1 stop9h 06m
Deal found 8/17![Delta logo]()
$366
Last-minute flights from Calgary to O'Hare IntlDiscover last-minute flight deals from Calgary to O'Hare Intl. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated August 19, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:00 pm -
Nonstop3h 40m
Sun 9/65:30 pm -
Nonstop3h 55m
Deal found 8/17![WestJet logo]()
$249
This SmartFares deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:00 pm -
Nonstop3h 40m
Sun 9/135:30 pm -
Nonstop3h 55m
Deal found 8/15![WestJet logo]()
$266
This FlightHub deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:00 pm -
Nonstop3h 40m
Tue 9/155:30 pm -
Nonstop3h 55m
Deal found 8/16![WestJet logo]()
$246
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:45 am -
1 stop8h 15m
Tue 9/158:30 pm -
Nonstop3h 59m
Deal found 8/13![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:30 am -
Nonstop3h 35m
Wed 10/288:40 am -
Nonstop3h 55m
Deal found 8/17![United Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:30 am -
Nonstop3h 35m
Tue 10/278:40 am -
1 stop14h 13m
Deal found 8/17![United Airlines logo]()
$275
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:00 pm -
Nonstop3h 40m
Sun 9/205:30 pm -
Nonstop3h 55m
Deal found 8/18![WestJet logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:00 pm -
Nonstop3h 40m
Fri 9/255:30 pm -
Nonstop3h 55m
Deal found 8/13![WestJet logo]()
$263
This Trip.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:00 pm -
Nonstop3h 40m
Mon 9/285:30 pm -
Nonstop3h 55m
Deal found 8/14![WestJet logo]()
$257
This Traveloka deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:55 pm -
1 stop8h 05m
Mon 10/55:30 pm -
Nonstop3h 55m
Deal found 8/14![Multiple Airlines logo]()
$245
One-way flights from Calgary to O'Hare IntlSearch for one-way flight options from Calgary to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
Search for one-way flight options from Calgary to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Flysmarter deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:55 pm -
1 stop8h 05m
Deal found 8/17![Air Canada logo]()
$172
This Air Canada deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:55 pm -
1 stop8h 05m
Deal found 8/17![Air Canada logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:45 am -
1 stop14h 38m
Deal found 8/14![Multiple Airlines logo]()
$175
This Air Canada deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:00 am -
1 stop8h 15m
Deal found 8/14![Air Canada logo]()
$176
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:51 pm -
Nonstop3h 45m
Deal found 8/17![American Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:30 pm -
Nonstop3h 35m
Deal found 8/17![United Airlines logo]()
$178
This Air Canada deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:55 am -
1 stop7h 05m
Deal found 8/14![Air Canada logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:00 pm -
2 stops13h 51m
Deal found 8/17![Multiple Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
2 stops8h 56m
Deal found 8/17![Delta logo]()
$183
This Air Canada deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:30 pm -
2 stops11h 30m
Deal found 8/14![Air Canada logo]()
$184
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Traveloka) |
One-way from | $172 (Flysmarter) |
Popular in | July |
Cheapest in | May |
Average price | $349 |
Good round-trip deal | $370 or less |
Good one-way deal | $242 or less |
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 2,558,603 searches. Data last updated August 19, 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
Cheapest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 10/28
6:35 am-6:10 pm
1 stop10h 35m
Chicago O'Hare Intl
Fri 10/30
12:29 pm-8:40 pm
1 stop9h 11m
$277
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 8/28
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Sun 9/6
6:00 am-12:55 pm
1 stop7h 55m
$306
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sun 8/30
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Wed 9/2
2:00 pm-11:04 pm
1 stop10h 04m
$312
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 10/30
6:35 am-6:10 pm
1 stop10h 35m
Chicago O'Hare Intl
Mon 11/2
8:29 am-10:40 pm
2 stops14h 11m
$333
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 9/3
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Sun 9/6
6:00 am-12:55 pm
1 stop7h 55m
$334
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 8/28
8:30 am-1:05 pm
Nonstop3h 35m
Chicago O'Hare Intl
Sat 8/29
8:44 am-11:32 am
Nonstop3h 48m
$342
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sat 11/21
12:15 pm-8:34 pm
2 stops8h 19m
Chicago O'Hare Intl
Tue 12/1
8:29 am-9:45 pm
2 stops13h 16m
$349
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sun 9/6
12:00 pm-4:40 pm
Nonstop3h 40m
Chicago O'Hare Intl
Fri 9/11
5:30 pm-8:25 pm
Nonstop3h 55m
$355
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 10/2
12:00 pm-4:40 pm
Nonstop3h 40m
Chicago O'Hare Intl
Fri 10/9
5:30 pm-8:25 pm
Nonstop3h 55m
$361
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 9/2
6:45 am-5:41 pm
1 stop9h 56m
Chicago O'Hare Intl
Sat 9/5
12:29 pm-8:35 pm
1 stop9h 06m
$366
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Calgary to O'Hare Intl
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to O'Hare Intl in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Calgary-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Calgary-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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
How far ahead should I book a flight from Calgary to Chicago O'Hare Intl Airport?
To ensure you get the cheapest price possible for a flight from Calgary to Chicago O'Hare Intl Airport, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 $252). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $395). 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 August 19, 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.
The best insider tips for Calgary to Chicago O'Hare Intl Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Calgary to Chicago O'Hare Intl Airport trip
Our travel experts
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 August 19, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andWestJet from Calgary to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
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.
Traveling 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 locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Gurnee
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
Racine
Great Lakes
Janesville
Joliet
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
O'Hare Intl flight routes
Other flight options
Other flights from Calgary
Popular flights
Alternative routes for Calgary to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Calgary to O'Hare Intl by cabin class
Find flights from Calgary to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 19, 2026.
Calgary and O'Hare Intl flights
Browse other Calgary and O'Hare Intl flight options. Last updated on August 19, 2026.
Other flights from Calgary
Browse through other flights departing from Calgary. Flights are based on user searches made on Cheapflights and were last updated on August 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$391 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$149 | Average$335 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$283 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$208 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$371 | FlexibilityNo cancel fee | On-timeN/A |