$148+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Jun 21 — Jun 281
Round-trip
1 adult, Economy
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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 November or March, booked 78 days in advance, depart on a Friday or Sunday and return on a Friday
Cheap flight deals from Calgary to O'Hare Intl
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Best
Last-minute
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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 May 22, 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 May 22, 2026.
This American Airlines deal was found by Cheapflights users on 5/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Mon 5/2510:00 am
ORD
- YYC
Nonstop3h 44m
American Airlines
Deal found 5/18![American Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 5/20. 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 8/206:45 am
YYC
- ORD
1 stop9h 19m
Delta
Wed 8/2612:29 pm
ORD
- YYC
1 stop9h 06m
Delta
Deal found 5/20![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 5/19. 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 8/146:45 am
YYC
- ORD
1 stop9h 19m
Delta
Tue 8/188:48 am
ORD
- YYC
2 stops12h 47m
Delta
Deal found 5/19![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 5/19. 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 8/127:45 am
YYC
- ORD
1 stop9h 34m
Delta
Wed 8/191:59 pm
ORD
- YYC
1 stop10h 00m
Delta
Deal found 5/19![Delta logo]()
$253
This Air Canada deal was found by Cheapflights users on 5/21. 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
YYC
- ORD
1 stop8h 05m
Air Canada
Tue 10/63:45 pm
ORD
- YYC
1 stop8h 12m
Air Canada
Deal found 5/21![Air Canada logo]()
$257
This Delta deal was found by Cheapflights users on 5/20. 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 8/217:45 am
YYC
- ORD
1 stop9h 34m
Delta
Wed 8/2612:29 pm
ORD
- YYC
1 stop9h 06m
Delta
Deal found 5/20![Delta logo]()
$258
This oojo deal was found by Cheapflights users on 5/18. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Mon 9/215:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 5/18![WestJet logo]()
$259
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Mon 5/256:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Mon 5/258:55 pm
ORD
- YYC
Nonstop3h 48m
American Airlines
Deal found 5/21![American Airlines logo]()
$261
This oojo deal was found by Cheapflights users on 5/17. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Fri 10/235:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 5/17![WestJet logo]()
$262
This Trip.com deal was found by Cheapflights users on 5/19. 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.
Tue 6/912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sat 6/135:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 5/19![WestJet logo]()
$264
This Delta deal was found by Cheapflights users on 5/20. 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 8/197:45 am
YYC
- ORD
1 stop9h 34m
Delta
Wed 8/2612:29 pm
ORD
- YYC
1 stop9h 06m
Delta
Deal found 5/20![Delta 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 May 22, 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 May 22, 2026.
This Delta deal was found by Cheapflights users on 5/18. 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.
Mon 9/147:15 am
YYC
- ORD
1 stop9h 46m
Delta
Mon 9/2112:15 pm
ORD
- YYC
1 stop9h 29m
Delta
Deal found 5/18![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Tue 7/216:00 am
YYC
- ORD
1 stop14h 39m
United Airlines
Mon 7/275:00 am
ORD
- YYC
1 stop14h 10m
United Airlines
Deal found 5/21![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 5/17. 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 10/217:45 am
YYC
- ORD
1 stop6h 12m
Delta
Fri 10/231:55 pm
ORD
- YYC
1 stop10h 18m
Delta
Deal found 5/17![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 5/17. 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 7/297:45 am
YYC
- ORD
1 stop10h 12m
Delta
Mon 8/312:29 pm
ORD
- YYC
1 stop9h 06m
Delta
Deal found 5/17![Delta logo]()
$318
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Wed 8/196:00 am
YYC
- ORD
1 stop15h 46m
United Airlines
Fri 8/217:45 pm
ORD
- YYC
Nonstop3h 51m
United Airlines
Deal found 5/21![United Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Mon 10/1912:30 pm
YYC
- ORD
Nonstop3h 35m
United Airlines
Tue 10/208:40 am
ORD
- YYC
Nonstop3h 48m
United Airlines
Deal found 5/21![United Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 5/18. 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.
Mon 6/87:40 am
YYC
- ORD
1 stop10h 18m
Delta
Sat 6/135:30 pm
ORD
- YYC
Nonstop3h 55m
Delta
Deal found 5/18![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 6/166:00 am
YYC
- ORD
1 stop15h 49m
United Airlines
Tue 6/237:45 pm
ORD
- YYC
Nonstop3h 52m
United Airlines
Deal found 5/17![United Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 5/19. 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 8/296:45 am
YYC
- ORD
1 stop9h 48m
Delta
Sat 9/1212:15 pm
ORD
- YYC
2 stops11h 51m
Delta
Deal found 5/19![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 6/1712:25 pm
YYC
- ORD
2 stops8h 00m
Delta
Wed 6/246:55 am
ORD
- YYC
1 stop7h 15m
Delta
Deal found 5/18![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 5/21. 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 8/197:45 am
YYC
- ORD
1 stop9h 34m
Delta
Mon 8/245:30 pm
ORD
- YYC
Nonstop3h 55m
Delta
Deal found 5/21![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 5/21. 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 8/197:45 am
YYC
- ORD
1 stop9h 34m
Delta
Sun 8/235:30 pm
ORD
- YYC
Nonstop3h 55m
Delta
Deal found 5/21![Delta logo]()
$385
Last-minute flights from Calgary to O'Hare IntlDiscover last-minute flight deals from Calgary to O'Hare Intl. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated May 22, 2026 and is based on user searches.
This Flysmarter deal was found by Cheapflights users on 5/19. 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 5/216:30 am
YYC
- ORD
1 stop7h 25m
Multiple Airlines
Wed 5/277:44 pm
ORD
- YYC
Nonstop3h 53m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 5/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Mon 5/2510:00 am
ORD
- YYC
Nonstop3h 44m
American Airlines
Deal found 5/18![American Airlines logo]()
$244
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Mon 5/256:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Mon 5/258:55 pm
ORD
- YYC
Nonstop3h 48m
American Airlines
Deal found 5/21![American Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 5/268:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Sat 5/307:44 pm
ORD
- YYC
Nonstop3h 53m
United Airlines
Deal found 5/19![United Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 5/266:45 am
YYC
- ORD
2 stops12h 29m
Delta
Sat 5/305:00 pm
ORD
- YYC
1 stop6h 57m
Delta
Deal found 5/19![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 5/267:45 am
YYC
- ORD
1 stop10h 05m
Delta
Mon 6/112:30 pm
ORD
- YYC
1 stop9h 00m
Delta
Deal found 5/19![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/20. 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 5/286:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Mon 6/16:00 am
ORD
- YYC
1 stop16h 43m
American Airlines
Deal found 5/20![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Sat 5/306:15 am
YYC
- ORD
Nonstop3h 30m
American Airlines
Sun 5/315:00 am
ORD
- YYC
1 stop17h 43m
American Airlines
Deal found 5/20![American Airlines logo]()
$274
This Trip.com deal was found by Cheapflights users on 5/19. 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.
Mon 6/812:55 am
YYC
- ORD
1 stop7h 05m
Multiple Airlines
Sat 6/135:30 pm
ORD
- YYC
Nonstop3h 55m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$288
This Trip.com deal was found by Cheapflights users on 5/19. 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.
Tue 6/912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sat 6/135:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 5/19![WestJet logo]()
$264
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 May 22, 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 May 22, 2026.
This American Airlines deal was found by Cheapflights users on 5/20. 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 5/281:40 pm
YYC
- ORD
Nonstop3h 45m
American Airlines
Deal found 5/20![American Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 6/212:28 pm
YYC
- ORD
Nonstop3h 37m
United Airlines
Deal found 5/19![United Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 5/18. 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.
Mon 10/512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 5/18![WestJet logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/21. 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.
Thu 9/2412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 5/21![WestJet logo]()
$152
This Justfly.com deal was found by Cheapflights users on 5/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 5/21![WestJet logo]()
$154
This Delta deal was found by Cheapflights users on 5/20. 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 11/187:45 am
YYC
- ORD
1 stop6h 12m
Delta
Deal found 5/20![Delta logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 11/169:00 am
YYC
- ORD
Nonstop3h 35m
WestJet
Deal found 5/19![WestJet logo]()
$156
This United Airlines deal was found by Cheapflights users on 5/17. 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 5/288:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Deal found 5/17![United Airlines logo]()
$160
This American Airlines deal was found by Cheapflights users on 5/21. 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 6/47:00 am
YYC
- ORD
Nonstop3h 35m
American Airlines
Deal found 5/21![American Airlines logo]()
$161
This Air Canada deal was found by Cheapflights users on 5/21. 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.
Sat 6/66:30 am
YYC
- ORD
1 stop7h 25m
Air Canada
Deal found 5/21![Air Canada logo]()
$162
This Air Canada deal was found by Cheapflights users on 5/20. 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
YYC
- ORD
1 stop8h 05m
Air Canada
Deal found 5/20![Air Canada logo]()
$163
This Delta deal was found by Cheapflights users on 5/18. 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.
Mon 6/17:45 am
YYC
- ORD
1 stop10h 05m
Delta
Deal found 5/18![Delta logo]()
$164
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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Delta) |
One-way from | $148 (American Airlines) |
Popular in | July |
Cheapest in | November |
Average price | $254 |
Good round-trip deal | $188 or less |
Good one-way deal | $178 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 May 22, 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 - ORD
YYCORD
Calgary
Mon 9/14
7:15 am-6:01 pm
1 stop9h 46m
Chicago O'Hare Intl
Mon 9/21
12:15 pm-8:44 pm
1 stop9h 29m
$277
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Tue 7/21
6:00 am-9:39 pm
1 stop14h 39m
Chicago O'Hare Intl
Mon 7/27
5:00 am-6:10 pm
1 stop14h 10m
$277
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 10/21
7:45 am-2:57 pm
1 stop6h 12m
Chicago O'Hare Intl
Fri 10/23
1:55 pm-11:13 pm
1 stop10h 18m
$292
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 7/29
7:45 am-6:57 pm
1 stop10h 12m
Chicago O'Hare Intl
Mon 8/3
12:29 pm-8:35 pm
1 stop9h 06m
$318
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 6/8
7:40 am-6:58 pm
1 stop10h 18m
Chicago O'Hare Intl
Sat 6/13
5:30 pm-8:25 pm
Nonstop3h 55m
$355
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sat 8/29
6:45 am-5:33 pm
1 stop9h 48m
Chicago O'Hare Intl
Sat 9/12
12:15 pm-11:06 pm
2 stops11h 51m
$364
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 6/17
12:25 pm-9:25 pm
2 stops8h 00m
Chicago O'Hare Intl
Wed 6/24
6:55 am-1:10 pm
1 stop7h 15m
$373
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 8/19
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Mon 8/24
5:30 pm-8:25 pm
Nonstop3h 55m
$385
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 8/19
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Sun 8/23
5:30 pm-8:25 pm
Nonstop3h 55m
$385
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 8/19
6:00 am-10:46 pm
1 stop15h 46m
Chicago O'Hare Intl
Fri 8/21
7:45 pm-10:36 pm
Nonstop3h 51m
$387
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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
- 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 77 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, November is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of $248). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $353). 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 May 22, 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 May 22, 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.
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
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 locationsRosemont
Schaumburg
Benton Harbor
Naperville
Delavan
Oakbrook Terrace
Lake Geneva
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Great Lakes
Arlington Heights
Northbrook
Waukegan
Rockford
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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 May 22, 2026.
Calgary and O'Hare Intl flights
Browse other Calgary and O'Hare Intl flight options. Last updated on May 22, 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 May 22, 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$134 | Average$335 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$135 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$274 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$208 | Average$391 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$241 | Average$371 | FlexibilityNo cancel fee | On-timeN/A |