$147+ Cheap flights from Chicago (CHI) to Calgary (YYC)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Calgary 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 Chicago to Calgary are usually found in January or February, booked 64 days in advance, depart on a Friday or Tuesday and return on a Friday
Cheap flight deals from Chicago to Calgary
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Cheapest flights from Chicago to CalgaryExplore the most affordable flight options available from Chicago to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Chicago to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This Travelocity deal was found by Cheapflights users on 9/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:00 am -
1 stop13h 37m
Tue 12/158:07 am -
1 stop8h 42m
Deal found 9/30![Alaska Airlines logo]()
$321
This Expedia deal was found by Cheapflights users on 9/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:00 am -
1 stop13h 37m
Mon 12/148:07 am -
2 stops28h 03m
Deal found 9/30![Alaska Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/2210:00 am -
Nonstop3h 51m
Tue 10/271:51 pm -
Nonstop3h 45m
Deal found 9/30![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 10/2210:00 am -
Nonstop3h 51m
Wed 10/281:51 pm -
Nonstop3h 45m
Deal found 10/2![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 10/1510:00 am -
Nonstop3h 51m
Tue 10/201:51 pm -
Nonstop3h 45m
Deal found 10/1![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/215:00 am -
1 stop7h 59m
Fri 10/231:51 pm -
Nonstop3h 45m
Deal found 9/30![American Airlines logo]()
$353
This Air Canada deal was found by Cheapflights users on 10/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/83:45 pm -
1 stop10h 05m
Fri 12/117:00 am -
1 stop7h 38m
Deal found 10/5![Air Canada logo]()
$354
This Air Canada deal was found by Cheapflights users on 10/3. 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.
Sat 12/57:05 am -
1 stop11h 05m
Mon 12/71:45 am -
1 stop8h 22m
Deal found 10/3![Air Canada logo]()
$358
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:00 am -
1 stop13h 37m
Fri 12/119:07 am -
1 stop7h 42m
Deal found 10/1![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 10/2. 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.
Sat 10/2412:27 pm -
1 stop9h 13m
Tue 10/277:45 am -
1 stop8h 02m
Deal found 10/2![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 9/30. 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 10/2812:27 pm -
1 stop9h 13m
Wed 11/48:45 am -
2 stops12h 48m
Deal found 9/30![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 9/30. 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 10/1912:27 pm -
1 stop9h 13m
Sat 10/247:45 am -
2 stops13h 48m
Deal found 9/30![Delta logo]()
$383
Best flights from Chicago to CalgaryDiscover carefully curated flight deals from Chicago to Calgary that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Chicago to Calgary that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This Delta deal was found by Cheapflights users on 10/2. 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 10/1912:27 pm -
1 stop9h 13m
Sat 10/247:45 am -
2 stops13h 48m
Deal found 10/2![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 10/1. 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 12/18:40 am -
Nonstop4h 55m
Wed 12/93:06 pm -
1 stop7h 53m
Deal found 10/1![United Airlines logo]()
$413
This United deal was found by Cheapflights users on 10/4. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 am -
Nonstop3h 48m
Sat 10/2412:25 am -
1 stop7h 58m
Deal found 10/4![Multiple Airlines logo]()
$436
This Alaska Airlines deal was found by Cheapflights users on 9/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:08 pm -
2 stops32h 25m
Sun 1/109:00 am -
2 stops27h 13m
Deal found 9/30![Alaska Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 10/3. 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.
Thu 12/32:04 pm -
1 stop11h 17m
Tue 12/81:43 pm -
1 stop7h 13m
Deal found 10/3![Delta logo]()
$415
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:40 am -
Nonstop3h 55m
Sat 10/316:00 am -
1 stop7h 54m
Deal found 10/4![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 10/3. 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 12/412:39 pm -
2 stops12h 42m
Wed 12/98:45 am -
1 stop7h 05m
Deal found 10/3![Delta logo]()
$430
This United deal was found by Cheapflights users on 10/1. 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.
Sun 1/310:00 pm -
1 stop18h 21m
Thu 1/71:20 am -
1 stop6h 48m
Deal found 10/1![Multiple Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 10/3. 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 12/318:40 am -
Nonstop4h 55m
Thu 1/71:37 pm -
Nonstop2h 33m
Deal found 10/3![United Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 10/2. 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 10/2912:27 pm -
1 stop9h 13m
Sun 11/18:45 am -
1 stop7h 02m
Deal found 10/2![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 10/4. 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.
Sat 10/2412:30 pm -
1 stop9h 10m
Mon 10/266:35 am -
1 stop10h 35m
Deal found 10/4![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 10/3. 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.
Thu 10/1512:27 pm -
1 stop9h 13m
Tue 10/207:45 am -
2 stops13h 48m
Deal found 10/3![Delta logo]()
$472
This Delta deal was found by Cheapflights users on 10/3. 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 10/162:03 pm -
1 stop10h 07m
Tue 10/206:35 am -
2 stops12h 55m
Deal found 10/3![Delta logo]()
$472
This Delta deal was found by Cheapflights users on 10/3. 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 12/712:39 pm -
1 stop10h 28m
Wed 12/98:45 am -
1 stop7h 05m
Deal found 10/3![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 10/2212:30 pm -
1 stop9h 10m
Sun 10/256:35 am -
1 stop10h 35m
Deal found 10/4![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 10/4. 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 10/218:29 am -
2 stops13h 11m
Mon 10/266:35 am -
2 stops12h 55m
Deal found 10/4![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 10/3. 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.
Wed 12/1612:39 pm -
1 stop10h 28m
Sun 12/208:45 am -
1 stop7h 39m
Deal found 10/3![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 10/1. 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.
Mon 12/712:39 pm -
1 stop10h 28m
Sun 12/138:45 am -
1 stop7h 05m
Deal found 10/1![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 10/2. 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 12/316:00 am -
2 stops15h 30m
Mon 1/41:25 am -
1 stop7h 27m
Deal found 10/2![Delta logo]()
$617
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 12/310:24 am -
2 stops14h 57m
Mon 12/78:45 am -
1 stop7h 05m
Deal found 10/4![Delta logo]()
$620
This Delta deal was found by Cheapflights users on 10/1. 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.
Thu 10/2212:27 pm -
1 stop9h 13m
Wed 10/287:45 am -
1 stop8h 02m
Deal found 10/1![Delta logo]()
$631
Last-minute flights from Chicago to CalgaryDiscover last-minute flight deals from Chicago to Calgary. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Calgary. Data last updated October 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 10/1510:00 am -
Nonstop3h 51m
Tue 10/201:51 pm -
Nonstop3h 45m
Deal found 10/1![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 10/162:50 pm -
1 stop7h 54m
Tue 10/201:51 pm -
Nonstop3h 45m
Deal found 10/2![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 9/30. 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 10/1912:27 pm -
1 stop9h 13m
Sat 10/247:45 am -
2 stops13h 48m
Deal found 9/30![Delta logo]()
$383
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/215:00 am -
1 stop7h 59m
Fri 10/231:51 pm -
Nonstop3h 45m
Deal found 9/30![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 10/2. 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 10/215:00 am -
1 stop7h 59m
Fri 10/301:51 pm -
Nonstop3h 45m
Deal found 10/2![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/2210:00 am -
Nonstop3h 51m
Tue 10/271:51 pm -
Nonstop3h 45m
Deal found 9/30![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 10/2210:00 am -
Nonstop3h 51m
Wed 10/281:51 pm -
Nonstop3h 45m
Deal found 10/2![American Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 9/30. 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 10/232:03 pm -
1 stop10h 07m
Tue 10/277:45 am -
1 stop5h 51m
Deal found 9/30![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 10/2. 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.
Sat 10/2412:27 pm -
1 stop9h 13m
Tue 10/277:45 am -
1 stop8h 02m
Deal found 10/2![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 9/30. 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 10/2812:30 pm -
1 stop9h 10m
Wed 11/41:33 pm -
1 stop7h 32m
Deal found 9/30![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 9/30. 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 10/2812:27 pm -
1 stop9h 13m
Wed 11/48:45 am -
2 stops12h 48m
Deal found 9/30![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 9/30. 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 10/302:03 pm -
1 stop10h 07m
Tue 11/31:33 pm -
1 stop7h 32m
Deal found 9/30![Delta logo]()
$360
One-way flights from Chicago to CalgarySearch for one-way flight options from Chicago to Calgary. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Chicago to Calgary. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/3010:00 am -
Nonstop3h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 10/2210:00 am -
Nonstop3h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 10/1. 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.
Sun 11/296:23 am -
1 stop7h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$153
This Air Canada deal was found by Cheapflights users on 10/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:05 am -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Air Canada logo]()
$155
This Delta deal was found by Cheapflights users on 10/3. 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 10/302:03 pm -
1 stop10h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 10/1. 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.
Thu 11/510:12 am -
2 stops14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 10/1. 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.
Sat 10/3112:30 pm -
2 stops11h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$158
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 10/2010:00 am -
Nonstop3h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$160
This Delta deal was found by Cheapflights users on 9/30. 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 10/2012:27 pm -
1 stop9h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 9/30. 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 10/2012:30 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 10/2. 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.
Sat 10/2412:27 pm -
2 stops11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$162
This Delta deal was found by Cheapflights users on 10/2. 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.
Sat 10/2412:30 pm -
2 stops11h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$162
Find flight deals from Chicago to Calgary
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Calgary (YYC). 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 October 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Travelocity) |
One-way from | $147 (American Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $393 |
Good round-trip deal | $337 or less |
Good one-way deal | $168 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Calgary that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Tue 12/1
12:34 pm-11:07 pm
1 stop10h 33m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
ChicagoCalgary
MDW Chicago Midway - YYC Calgary
MDWYYC
Chicago Midway
Thu 11/5
10:12 am-1:10 am
2 stops14h 58m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
ChicagoCalgary
MDW Chicago Midway - YYC Calgary
MDWYYC
Chicago Midway
Tue 10/20
12:27 pm-8:40 pm
1 stop9h 13m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$161
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Mon 10/19
2:03 pm-11:10 pm
1 stop10h 07m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$161
ChicagoCalgary
MDW Chicago Midway - YYC Calgary
MDWYYC
Chicago Midway
Sat 10/24
12:27 pm-11:12 pm
2 stops11h 45m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Sat 10/24
12:30 pm-11:12 pm
2 stops11h 42m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Tue 10/20
8:29 am-8:40 pm
2 stops13h 11m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$166
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Wed 10/21
8:29 am-8:40 pm
2 stops13h 11m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$166
Quickest round-trip
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Sat 10/24
8:40 am-11:28 am
Nonstop3h 48m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Thu 10/22
6:00 am-1:53 pm
1 stop8h 53m
Calgary
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
Showing 1-10 of 37 resultsSorted by cheapest first
Compare providers for flights from Chicago to Calgary
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 Chicago to Calgary in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Calgary flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Calgary flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Calgary flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Calgary 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 Chicago-Calgary 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 Chicago to Calgary
Have a flexible travel schedule? Discover the best time to fly to Calgary from Chicago with our price prediction graph.
CHI-YYC
ORD-YYC
MDW-YYC
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 Chicago to Calgary
CHI-YYC
ORD-YYC
MDW-YYC
What is the cheapest month to book a flight from Chicago to Calgary?
Currently, January is the cheapest month in which you can book a flight from Chicago to Calgary (average of $229). Flying from Chicago to Calgary in July is currently the most expensive (average of $448). 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 CHI to YYC?
Find hourly flight availability from Chicago to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 5, 2026.
One of the essential ways to save on airfare from Chicago to Calgary is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 41% on airfare.
Weekly flight availability from Chicago to Calgary
Explore weekly flight availability from Chicago to Calgary. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 5, 2026.
The most flights from CHI to YYC are scheduled on a Friday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Calgary?
Airfare is typical for this route at the moment.
Chicago to Calgary flights typically cost between $278 and $480 in January.The cheapest round-trip price found within the last 5 days was $335 on American Airlines (Jan 15-Jan 22).
What’s the top layover airport for flights from Chicago to Calgary?
Share of 1-stop round-trip flights from Chicago to Calgary chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Calgary on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Calgary?
Average round-trip fare for 1-stop flights from Chicago to Calgary, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $488.
What’s the fastest layover option from Chicago to Calgary?
Shortest average travel time for 1-stop one-way flights from Chicago to Calgary, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 27m.
Which airport typically offers the quickest layover for flights from Chicago to Calgary?
Average layover duration for 1-stop one-way flights from Chicago to Calgary, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 00m.
How often are flights from Chicago to Calgary delayed?
About 26% of weekly flights between Chicago and Calgary have experienced delays in the past year, with the average delay time being 144 minutes.
What is the most punctual flight time for Chicago to Calgary flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Calgary flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 24% of flights being delayed.
How far ahead should I book a flight from Chicago to Calgary?
The best time to book flights from Chicago to Calgary is 62 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Chicago to Calgary?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Calgary. Price data was last updated on October 3, 2026.
Travelers seeking maximum savings on their Chicago to Calgary flight should consider departing on Thursday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Calgary 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 Chicago to Calgary trip
Our travel experts
Reviews of airlines servicing Calgary
Get insights into the airlines that provide service to Calgary. 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 Calgary. Reviews last updated October 5, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andWestJet from Chicago to Calgary to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Calgary. 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 Calgary?
Book flights to Calgary if you plan to visit one of these locationsCanmore
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Top 6 airlines flying from Chicago to Calgary
Discover the top 6 airlines that operate flights from Chicago to Calgary. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$336 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$129 | Average$229 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$139 | Average$301 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$168 | Average$453 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$192 | Average$388 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$288 | Average$480 | FlexibilityNo cancel fee | On-time71% |