$164+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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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 May, booked 45 days in advance, depart on a Friday or Tuesday 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 July 6, 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 July 6, 2026.
This oojo deal was found by Cheapflights users on 7/4. 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.
Fri 10/309:00 am
YYC
- ORD
Nonstop3h 35m
WestJet
Mon 11/22:20 pm
ORD
- YYC
Nonstop4h 55m
WestJet
Deal found 7/4![WestJet logo]()
$207
This oojo deal was found by Cheapflights users on 7/1. 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.
Fri 9/1812:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Mon 9/215:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 7/1![WestJet logo]()
$260
This FlightHub deal was found by Cheapflights users on 7/2. 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 9/2412:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Sun 9/275:30 pm
ORD
- YYC
Nonstop3h 55m
WestJet
Deal found 7/2![WestJet logo]()
$264
This Delta deal was found by Cheapflights users on 7/6. 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 10/307:45 am
YYC
- ORD
2 stops12h 47m
Delta
Mon 11/22:03 pm
ORD
- YYC
1 stop10h 01m
Delta
Deal found 7/6![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 7/1. 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 10/2312:30 pm
YYC
- ORD
Nonstop3h 35m
United Airlines
Sat 11/72:18 pm
ORD
- YYC
1 stop8h 35m
United Airlines
Deal found 7/1![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Fri 9/47:00 am
YYC
- ORD
Nonstop3h 35m
American Airlines
Sun 9/68:46 pm
ORD
- YYC
Nonstop3h 56m
American Airlines
Deal found 7/3![American Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 7/1. 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 10/237:45 am
YYC
- ORD
1 stop7h 55m
Delta
Sat 11/78:05 am
ORD
- YYC
2 stops13h 25m
Delta
Deal found 7/1![Delta logo]()
$275
This United deal was found by Cheapflights users on 7/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:30 pm
YYC
- ORD
Nonstop3h 35m
Multiple Airlines
Mon 10/2610:15 am
ORD
- YYC
1 stop7h 39m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 7/2. 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 9/16:45 am
YYC
- ORD
1 stop9h 56m
Delta
Tue 9/82:05 pm
ORD
- YYC
1 stop10h 01m
Delta
Deal found 7/2![Delta logo]()
$279
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 July 6, 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 July 6, 2026.
This Delta deal was found by Cheapflights users on 7/1. 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 10/237:45 am
YYC
- ORD
1 stop7h 55m
Delta
Sat 11/712:33 pm
ORD
- YYC
1 stop8h 57m
Delta
Deal found 7/1![Delta logo]()
$275
This United deal was found by Cheapflights users on 7/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am
YYC
- ORD
1 stop13h 22m
Multiple Airlines
Sun 10/182:15 pm
ORD
- YYC
1 stop12h 02m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 7/4. 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 10/307:45 am
YYC
- ORD
2 stops12h 47m
Delta
Mon 11/212:33 pm
ORD
- YYC
2 stops11h 31m
Delta
Deal found 7/4![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 7/2. 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 12/259:00 am
YYC
- ORD
Nonstop2h 35m
Delta
Thu 12/311:55 pm
ORD
- YYC
1 stop10h 18m
Delta
Deal found 7/2![Delta logo]()
$316
This Delta deal was found by Cheapflights users on 7/3. 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
YYC
- ORD
Nonstop3h 40m
Delta
Tue 10/62:03 pm
ORD
- YYC
1 stop10h 01m
Delta
Deal found 7/3![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 7/5. 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
YYC
- ORD
1 stop9h 34m
Delta
Wed 9/92:05 pm
ORD
- YYC
2 stops9h 10m
Delta
Deal found 7/5![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 7/3. 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 8/26:45 am
YYC
- ORD
1 stop9h 32m
Delta
Thu 8/62:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/3![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 7/2. 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 8/317:45 am
YYC
- ORD
1 stop9h 34m
Delta
Thu 9/35:30 pm
ORD
- YYC
Nonstop3h 55m
Delta
Deal found 7/2![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 7/2. 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 8/267:00 am
YYC
- ORD
2 stops9h 41m
Delta
Fri 9/411:23 am
ORD
- YYC
1 stop11h 27m
Delta
Deal found 7/2![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 7/1. 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 7/226:45 am
YYC
- ORD
1 stop9h 14m
Delta
Fri 7/242:02 pm
ORD
- YYC
1 stop9h 56m
Delta
Deal found 7/1![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 7/4. 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
Mon 8/245:30 pm
ORD
- YYC
Nonstop3h 55m
Delta
Deal found 7/4![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 7/5. 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 7/296:45 am
YYC
- ORD
1 stop9h 14m
Delta
Mon 8/32:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/5![Delta logo]()
$425
Last-minute flights from Calgary to O'Hare IntlDiscover last-minute flight deals from Calgary to O'Hare Intl. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Calgary to O'Hare Intl. Data last updated July 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/88:30 am
YYC
- ORD
Nonstop3h 37m
United Airlines
Sat 8/86:00 am
ORD
- YYC
1 stop13h 10m
United Airlines
Deal found 7/3![United Airlines logo]()
$303
This Kissandfly.com deal was found by Cheapflights users on 7/4. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:00 am
YYC
- ORD
1 stop8h 16m
Air Canada
Sun 7/128:45 am
ORD
- YYC
1 stop10h 28m
Air Canada
Deal found 7/4![Air Canada logo]()
$305
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/912:28 pm
YYC
- ORD
Nonstop3h 36m
United Airlines
Sun 7/127:45 pm
ORD
- YYC
Nonstop3h 52m
United Airlines
Deal found 7/3![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 7/3. 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 7/107:45 am
YYC
- ORD
1 stop10h 12m
Delta
Thu 8/62:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/3![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 7/2. 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 7/166:45 am
YYC
- ORD
1 stop9h 14m
Delta
Mon 7/202:02 pm
ORD
- YYC
1 stop9h 56m
Delta
Deal found 7/2![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 7/4. 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 8/116:45 am
YYC
- ORD
1 stop9h 56m
Delta
Mon 8/242:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/4![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 7/3. 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 8/177:45 am
YYC
- ORD
1 stop9h 34m
Delta
Wed 8/192:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/3![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 7/6. 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 8/177:45 am
YYC
- ORD
1 stop9h 34m
Delta
Mon 8/242:00 pm
ORD
- YYC
1 stop10h 04m
Delta
Deal found 7/6![Delta logo]()
$300
This Air Canada deal was found by Cheapflights users on 7/2. 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 8/1811:55 pm
YYC
- ORD
1 stop8h 05m
Air Canada
Tue 8/258:40 am
ORD
- YYC
1 stop8h 28m
Air Canada
Deal found 7/2![Air Canada logo]()
$289
This Air Canada deal was found by Cheapflights users on 7/2. 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 8/256:30 am
YYC
- ORD
1 stop9h 27m
Air Canada
Tue 9/13:45 pm
ORD
- YYC
1 stop8h 15m
Air Canada
Deal found 7/2![Air Canada logo]()
$295
This Delta deal was found by Cheapflights users on 7/2. 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 8/277:45 am
YYC
- ORD
1 stop9h 34m
Delta
Mon 8/316:59 am
ORD
- YYC
2 stops14h 36m
Delta
Deal found 7/2![Delta logo]()
$292
This Air Canada deal was found by Cheapflights users on 7/2. 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 8/281:00 am
YYC
- ORD
1 stop8h 16m
Air Canada
Tue 9/13:45 pm
ORD
- YYC
1 stop8h 15m
Air Canada
Deal found 7/2![Air Canada logo]()
$290
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 July 6, 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 July 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 9/2512:00 pm
YYC
- ORD
Nonstop3h 40m
WestJet
Deal found 7/4![WestJet logo]()
$164
This Air Canada deal was found by Cheapflights users on 7/1. 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.
Wed 7/226:30 am
YYC
- ORD
1 stop7h 25m
Air Canada
Deal found 7/1![Air Canada logo]()
$165
This Air Canada deal was found by Cheapflights users on 7/1. 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 9/199:20 am
YYC
- ORD
2 stops9h 28m
Air Canada
Deal found 7/1![Air Canada logo]()
$166
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sun 8/308:00 am
YYC
- ORD
1 stop15h 01m
United Airlines
Deal found 7/3![United Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 7/1. 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 stop15h 49m
United Airlines
Deal found 7/1![United Airlines logo]()
$168
This Air Canada deal was found by Cheapflights users on 7/6. 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 9/41:00 am
YYC
- ORD
1 stop8h 16m
Air Canada
Deal found 7/6![Air Canada logo]()
$170
This Air Canada deal was found by Cheapflights users on 7/2. 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 9/19:20 am
YYC
- ORD
2 stops9h 32m
Air Canada
Deal found 7/2![Air Canada logo]()
$171
This Air Canada deal was found by Cheapflights users on 7/3. 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.
Wed 8/196:30 am
YYC
- ORD
1 stop7h 20m
Air Canada
Deal found 7/3![Air Canada logo]()
$172
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/296:45 am
YYC
- ORD
1 stop15h 45m
American Airlines
Deal found 7/1![American Airlines logo]()
$174
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 9/307:00 am
YYC
- ORD
Nonstop3h 29m
American Airlines
Deal found 7/2![American Airlines logo]()
$176
This United Airlines deal was found by Cheapflights users on 7/6. 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 9/46:00 am
YYC
- ORD
1 stop16h 59m
United Airlines
Deal found 7/6![United Airlines logo]()
$177
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 July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (oojo) |
One-way from | $164 (Kiwi.com) |
Popular in | July |
Cheapest in | November |
Average price | $371 |
Good round-trip deal | $393 or less |
Good one-way deal | $231 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 July 6, 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
Fri 10/23
7:45 am-4:40 pm
1 stop7h 55m
Chicago O'Hare Intl
Sat 11/7
12:33 pm-8:30 pm
1 stop8h 57m
$275
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 10/30
7:45 am-9:32 pm
2 stops12h 47m
Chicago O'Hare Intl
Mon 11/2
12:33 pm-11:04 pm
2 stops11h 31m
$313
Quickest round-trip
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 12/25
9:00 am-12:35 pm
Nonstop2h 35m
Chicago O'Hare Intl
Thu 12/31
1:55 pm-11:13 pm
1 stop10h 18m
$316
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 10/14
6:00 am-8:22 pm
1 stop13h 22m
Chicago O'Hare Intl
Sun 10/18
2:15 pm-1:17 am
1 stop12h 02m
$318
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 10/2
12:00 pm-4:40 pm
Nonstop3h 40m
Chicago O'Hare Intl
Tue 10/6
2:03 pm-11:04 pm
1 stop10h 01m
$336
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 9/3
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Wed 9/9
2:05 pm-10:15 pm
2 stops9h 10m
$376
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sun 8/2
6:45 am-5:17 pm
1 stop9h 32m
Chicago O'Hare Intl
Thu 8/6
2:00 pm-11:04 pm
1 stop10h 04m
$406
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 8/31
7:45 am-6:19 pm
1 stop9h 34m
Chicago O'Hare Intl
Thu 9/3
5:30 pm-8:25 pm
Nonstop3h 55m
$409
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 8/26
7:00 am-5:41 pm
2 stops9h 41m
Chicago O'Hare Intl
Fri 9/4
11:23 am-9:50 pm
1 stop11h 27m
$414
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Wed 7/22
6:45 am-4:59 pm
1 stop9h 14m
Chicago O'Hare Intl
Fri 7/24
2:02 pm-10:58 pm
1 stop9h 56m
$417
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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 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 44 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 $245). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $371). 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 July 6, 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 July 6, 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
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Food
7.2
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 locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
South Holland
Libertyville
Hoffman Estates
Warrenville
Rockford
Racine
Great Lakes
Northbrook
Waukegan
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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 July 6, 2026.
Calgary and O'Hare Intl flights
Browse other Calgary and O'Hare Intl flight options. Last updated on July 6, 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 July 6, 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 July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$366 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$135 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$256 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$208 | Average$391 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$241 | Average$371 | FlexibilityNo cancel fee | On-timeN/A |