$180+ Cheap flights from Calgary (YYC) to Chicago (CHI)
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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Nov 19 — Nov 261
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Calgary to Chicago 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 are usually found in April or February, booked 52 days in advance, depart on a Friday or Sunday and return on a Friday
Cheap flight deals from Calgary to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Calgary to ChicagoExplore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:07 am -
1 stop7h 42m
Mon 12/76:47 pm -
1 stop27h 50m
Deal found 10/17![Alaska Airlines logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:09 am -
2 stops27h 00m
Wed 11/189:30 am -
1 stop13h 09m
Deal found 10/19![Alaska Airlines logo]()
$321
This Kissandfly.com deal was found by Cheapflights users on 10/18. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:51 pm -
Nonstop3h 45m
Wed 10/285:00 am -
1 stop7h 59m
Deal found 10/18![British Airways logo]()
$324
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:51 pm -
Nonstop3h 45m
Sun 10/255:00 am -
1 stop7h 59m
Deal found 10/17![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:45 am -
2 stops9h 20m
Tue 11/242:03 pm -
1 stop11h 14m
Deal found 10/15![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:45 am -
2 stops13h 09m
Tue 11/2412:30 pm -
2 stops12h 47m
Deal found 10/15![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:54 pm -
1 stop10h 05m
Wed 10/2810:00 am -
Nonstop3h 51m
Deal found 10/16![American Airlines logo]()
$332
This Kissandfly.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:51 pm -
Nonstop3h 45m
Fri 10/3010:00 am -
Nonstop3h 51m
Deal found 10/16![British Airways logo]()
$333
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:51 pm -
Nonstop3h 45m
Sat 10/2410:00 am -
Nonstop3h 51m
Deal found 10/19![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
1 stop7h 56m
Wed 11/42:03 pm -
1 stop11h 07m
Deal found 10/17![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
1 stop8h 02m
Tue 11/312:27 pm -
1 stop10h 13m
Deal found 10/17![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 am -
1 stop7h 55m
Thu 10/2911:19 am -
2 stops12h 51m
Deal found 10/15![Delta logo]()
$341
Best flights from Calgary to ChicagoDiscover carefully curated flight deals from Calgary to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Calgary to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/228:45 am -
1 stop7h 05m
Sun 1/2412:30 pm -
1 stop10h 24m
Deal found 10/16![Delta logo]()
$329
This United deal was found by Cheapflights users on 10/19. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:37 pm -
Nonstop2h 33m
Mon 11/233:50 pm -
1 stop10h 00m
Deal found 10/19![Multiple Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:37 pm -
Nonstop2h 33m
Mon 11/232:30 pm -
1 stop9h 23m
Deal found 10/16![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/218:45 am -
1 stop7h 05m
Sun 1/2412:30 pm -
1 stop10h 24m
Deal found 10/16![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:35 am -
2 stops9h 12m
Tue 11/312:27 pm -
2 stops12h 43m
Deal found 10/17![Delta logo]()
$343
This United deal was found by Cheapflights users on 10/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/171:37 pm -
Nonstop2h 33m
Thu 11/198:45 am -
1 stop16h 21m
Deal found 10/17![Multiple Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Wed 2/241:30 pm -
Nonstop2h 20m
Mon 3/11:05 pm -
1 stop10h 54m
Deal found 10/17![United Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:25 am -
2 stops10h 05m
Mon 11/232:03 pm -
1 stop11h 14m
Deal found 10/16![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/19. 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 11/37:25 am -
2 stops9h 35m
Tue 11/1012:30 pm -
1 stop10h 28m
Deal found 10/19![Delta logo]()
$345
This LATAM Airlines deal was found by Cheapflights users on 10/19. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1112:40 pm -
1 stop6h 18m
Fri 2/197:15 am -
1 stop13h 03m
Deal found 10/19![Multiple Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/198:45 am -
1 stop7h 05m
Thu 2/259:30 am -
2 stops13h 24m
Deal found 10/15![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:25 am -
2 stops8h 25m
Tue 12/1510:24 am -
2 stops14h 57m
Deal found 10/18![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:45 am -
2 stops9h 24m
Tue 12/1512:34 pm -
2 stops12h 47m
Deal found 10/18![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/18:45 am -
1 stop7h 02m
Sat 11/711:33 am -
2 stops13h 39m
Deal found 10/18![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/157:00 am -
2 stops8h 50m
Thu 2/2512:30 pm -
1 stop10h 24m
Deal found 10/15![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:45 am -
2 stops12h 48m
Thu 11/510:12 am -
2 stops14h 58m
Deal found 10/16![Delta logo]()
$473
Last-minute flights from Calgary to ChicagoDiscover last-minute flight deals from Calgary to Chicago. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Calgary to Chicago. Data last updated October 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:54 pm -
1 stop10h 05m
Wed 10/2810:00 am -
Nonstop3h 51m
Deal found 10/16![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:51 pm -
Nonstop3h 45m
Sat 10/2410:00 am -
Nonstop3h 51m
Deal found 10/19![American Airlines logo]()
$339
This Kissandfly.com deal was found by Cheapflights users on 10/18. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:51 pm -
Nonstop3h 45m
Wed 10/285:00 am -
1 stop7h 59m
Deal found 10/18![British Airways logo]()
$324
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:51 pm -
Nonstop3h 45m
Sun 10/255:00 am -
1 stop7h 59m
Deal found 10/17![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 am -
1 stop7h 55m
Thu 10/2912:30 pm -
1 stop9h 10m
Deal found 10/15![Delta logo]()
$341
This Kissandfly.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:51 pm -
Nonstop3h 45m
Fri 10/3010:00 am -
Nonstop3h 51m
Deal found 10/16![British Airways logo]()
$333
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:40 pm -
1 stop6h 47m
Mon 11/22:03 pm -
1 stop11h 07m
Deal found 10/17![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
1 stop8h 02m
Wed 11/412:27 pm -
1 stop10h 13m
Deal found 10/17![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
2 stops15h 12m
Thu 11/512:30 pm -
2 stops12h 40m
Deal found 10/17![Delta logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:09 am -
2 stops27h 00m
Wed 11/189:30 am -
1 stop13h 09m
Deal found 10/19![Alaska Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:45 am -
2 stops9h 20m
Tue 11/242:03 pm -
1 stop11h 14m
Deal found 10/15![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:45 am -
2 stops13h 09m
Tue 11/2412:30 pm -
2 stops12h 47m
Deal found 10/15![Delta logo]()
$328
One-way flights from Calgary to ChicagoSearch for one-way flight options from Calgary to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Calgary to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Trip.com deal was found by Cheapflights users on 10/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:09 am -
1 stop7h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Alaska Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:51 pm -
Nonstop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$182
This Alaska Airlines deal was found by Cheapflights users on 10/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/299:03 am -
1 stop7h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Alaska Airlines logo]()
$184
This SmartFares deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/69:07 am -
1 stop7h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Alaska Airlines logo]()
$186
This Trip.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:07 am -
1 stop7h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Alaska Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:25 am -
2 stops8h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$192
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:43 pm -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/157:30 am -
1 stop10h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:25 am -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$195
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 11/261:37 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$198
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:45 am -
2 stops11h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$198
Find flight deals from Calgary to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Chicago (CHI). 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 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (Alaska Airlines) |
One-way from | $180 (Trip.com) |
Popular in | March |
Cheapest in | April |
Average price | $293 |
Good round-trip deal | $386 or less |
Good one-way deal | $277 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Calgary to Chicago 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 20, 2026.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Tue 12/29
9:03 am-4:59 pm
1 stop7h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Tue 10/27
6:35 am-6:10 pm
1 stop10h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Tue 10/27
6:35 am-4:47 pm
2 stops9h 12m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 11/12
8:45 am-3:41 pm
1 stop6h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 12/14
7:25 am-5:06 pm
1 stop9h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 11/19
7:25 am-5:05 pm
1 stop9h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Thu 11/19
8:45 am-9:54 pm
2 stops13h 09m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 1/6
9:00 am-12:13 pm
2 stops27h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Fri 1/15
8:45 am-3:50 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Wed 1/6
8:45 am-3:50 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
Showing 1-10 of 31 resultsSorted by cheapest first
Compare providers for flights from Calgary to Chicago
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 Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Calgary-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Calgary-Chicago 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Calgary with our price prediction graph.
YYC-CHI
YYC-ORD
YYC-MDW
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
YYC-CHI
YYC-ORD
YYC-MDW
What is the cheapest month to book a flight from Calgary to Chicago?
Currently, May is the cheapest month in which you can book a flight from Calgary to Chicago (average of $260). Flying from Calgary to Chicago in June is currently the most expensive (average of $378). 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 CHI?
Find hourly flight availability from Calgary to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2026.
When flying from Calgary to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Calgary to Chicago
Explore weekly flight availability from Calgary to Chicago. 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 20, 2026.
The most flights from YYC to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Calgary to Chicago?
Airfare is typical for this route at the moment.
Calgary to Chicago flights typically cost between $216 and $433 in December.The cheapest round-trip price found within the last 5 days was $311 on Alaska Airlines (Dec 4-Dec 7).
How far ahead should I book a flight from Calgary to Chicago?
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
The best insider tips for Calgary to Chicago 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 trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 20, 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAmerican Airlines from Calgary to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Calgary to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Calgary
Popular flights
Alternative routes for Calgary to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Calgary to Chicago by cabin class
Find flights from Calgary to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Calgary and Chicago flights
Browse other Calgary and Chicago flight options. Last updated on October 20, 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 October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Calgary to Chicago
Discover the top 5 airlines that operate flights from Calgary to Chicago. 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$341 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$149 | Average$366 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$163 | Average$289 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$195 | Average$390 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$318 | FlexibilityNo cancel fee | On-timeN/A |