$106+ Cheap flights from Chicago (CHI) to Big Sky, MT
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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Big Sky 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 Big Sky are usually found in April or January, booked 52 days in advance, depart on a Tuesday or Saturday and return on a Thursday
Cheap flight deals from Chicago to Big Sky
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Cheapest flights from Chicago to Big SkyExplore the most affordable flight options available from Chicago to Big Sky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from Chicago to Big Sky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 am -
1 stop8h 54m
Sun 10/185:30 am -
1 stop5h 25m
Deal found 8/13![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:31 pm -
1 stop7h 26m
Sun 11/16:00 am -
1 stop4h 47m
Deal found 8/14![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/12. 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 9/257:40 pm -
1 stop5h 39m
Wed 9/306:00 am -
2 stops9h 59m
Deal found 8/12![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:45 pm -
2 stops12h 12m
Sat 10/176:00 am -
1 stop4h 47m
Deal found 8/13![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:44 pm -
1 stop5h 32m
Fri 9/43:55 pm -
1 stop4h 52m
Deal found 8/13![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:15 pm -
1 stop6h 50m
Fri 9/255:05 pm -
1 stop6h 25m
Deal found 8/13![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:29 pm -
1 stop5h 31m
Sat 9/268:25 am -
1 stop8h 35m
Deal found 8/12![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:00 pm -
1 stop7h 00m
Sat 9/266:17 am -
1 stop6h 03m
Deal found 8/12![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:27 pm -
2 stops12h 00m
Tue 10/276:00 am -
1 stop4h 47m
Deal found 8/13![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 8/12. 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 10/139:58 am -
Nonstop3h 27m
Tue 10/201:15 pm -
Nonstop3h 14m
Deal found 8/12![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:51 pm -
2 stops11h 28m
Wed 9/306:00 am -
2 stops9h 59m
Deal found 8/13![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:00 pm -
2 stops12h 19m
Wed 9/306:00 am -
2 stops11h 19m
Deal found 8/13![Delta logo]()
$318
Best flights from Chicago to Big SkyDiscover carefully curated flight deals from Chicago to Big Sky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from Chicago to Big Sky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:29 pm -
2 stops11h 02m
Sat 9/268:25 am -
1 stop8h 35m
Deal found 8/12![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:45 pm -
Nonstop3h 27m
Sun 10/258:00 am -
Nonstop3h 02m
Deal found 8/12![United Airlines logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:52 pm -
1 stop8h 07m
Wed 9/232:21 pm -
1 stop8h 38m
Deal found 8/16![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:45 pm -
2 stops9h 35m
Mon 10/264:15 pm -
1 stop7h 00m
Deal found 8/12![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:45 pm -
Nonstop3h 27m
Tue 10/2012:53 pm -
Nonstop3h 07m
Deal found 8/16![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/101:55 pm -
2 stops9h 26m
Sun 2/143:40 pm -
1 stop7h 06m
Deal found 8/13![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:35 am -
2 stops8h 15m
Tue 10/206:30 am -
2 stops9h 10m
Deal found 8/16![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:59 pm -
1 stop6h 11m
Thu 1/286:00 am -
2 stops11h 40m
Deal found 8/16![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:10 am -
Nonstop3h 23m
Sun 12/1312:30 pm -
Nonstop3h 00m
Deal found 8/15![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:25 am -
Nonstop3h 10m
Sun 10/45:00 am -
2 stops8h 15m
Deal found 8/13![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2412:30 pm -
2 stops12h 40m
Thu 1/286:00 am -
1 stop4h 51m
Deal found 8/16![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:56 pm -
1 stop6h 25m
Mon 9/214:32 pm -
1 stop5h 14m
Deal found 8/16![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:40 pm -
2 stops8h 50m
Fri 9/257:20 am -
2 stops8h 40m
Deal found 8/14![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:55 pm -
2 stops11h 32m
Mon 10/123:34 pm -
1 stop7h 00m
Deal found 8/14![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:15 pm -
Nonstop3h 27m
Mon 8/317:55 am -
Nonstop3h 04m
Deal found 8/16![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:00 pm -
1 stop8h 45m
Wed 9/306:55 am -
1 stop10h 05m
Deal found 8/16![Southwest logo]()
$430
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
1 stop8h 28m
Mon 1/1112:30 pm -
Nonstop3h 00m
Deal found 8/16![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:51 pm -
1 stop8h 11m
Sat 9/511:27 am -
2 stops10h 09m
Deal found 8/15![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:25 am -
Nonstop3h 10m
Fri 9/48:35 am -
2 stops8h 40m
Deal found 8/16![Southwest logo]()
$430
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:45 pm -
Nonstop3h 27m
Sun 10/184:30 pm -
1 stop6h 29m
Deal found 8/13![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:59 am -
1 stop5h 51m
Sat 9/511:27 am -
2 stops10h 09m
Deal found 8/14![Delta logo]()
$424
Last-minute flights from Chicago to Big SkyDiscover last-minute flight deals from Chicago to Big Sky. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Big Sky. Data last updated August 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:44 pm -
1 stop5h 32m
Fri 9/43:55 pm -
1 stop4h 52m
Deal found 8/13![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:15 am -
1 stop9h 35m
Fri 9/45:05 pm -
1 stop6h 25m
Deal found 8/13![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
2 stops9h 26m
Sat 9/126:00 am -
1 stop4h 55m
Deal found 8/12![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:29 pm -
1 stop5h 31m
Sat 9/268:25 am -
1 stop8h 35m
Deal found 8/12![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:00 pm -
1 stop7h 00m
Sat 9/266:17 am -
1 stop6h 03m
Deal found 8/12![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:15 pm -
1 stop6h 50m
Fri 9/255:05 pm -
1 stop6h 25m
Deal found 8/13![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:51 pm -
2 stops11h 28m
Wed 9/306:00 am -
2 stops9h 59m
Deal found 8/13![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:00 pm -
2 stops12h 19m
Wed 9/306:00 am -
2 stops11h 19m
Deal found 8/13![Delta logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:50 pm -
Nonstop3h 27m
Fri 9/254:30 pm -
1 stop5h 16m
Deal found 8/13![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 8/12. 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 9/257:40 pm -
1 stop5h 39m
Wed 9/306:00 am -
2 stops9h 59m
Deal found 8/12![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:50 am -
Nonstop3h 05m
Mon 10/56:15 pm -
1 stop10h 25m
Deal found 8/14![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/304:45 pm -
Nonstop3h 27m
Wed 10/72:37 pm -
1 stop7h 09m
Deal found 8/12![United Airlines logo]()
$321
One-way flights from Chicago to Big SkySearch for one-way flight options from Chicago to Big Sky. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from Chicago to Big Sky. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Wed 9/91:21 pm -
1 stop29h 33m
Deal found 8/12![Multiple Airlines logo]()
$106
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/107:00 am -
1 stop8h 33m
Deal found 8/14![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:31 pm -
1 stop6h 58m
Deal found 8/14![Delta logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am -
1 stop27h 06m
Deal found 8/14![Multiple Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:05 am -
1 stop7h 35m
Deal found 8/14![Southwest logo]()
$111
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/139:30 am -
2 stops13h 51m
Deal found 8/14![Delta logo]()
$114
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:59 am -
2 stops13h 58m
Deal found 8/14![Delta logo]()
$114
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:20 am -
2 stops9h 05m
Deal found 8/13![Southwest logo]()
$116
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:40 pm -
1 stop5h 39m
Deal found 8/13![Delta logo]()
$131
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop8h 21m
Deal found 8/13![Delta logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:30 am -
2 stops39h 22m
Deal found 8/14![Multiple Airlines logo]()
$132
This Delta deal was found by Cheapflights users on 8/12. 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 9/86:24 pm -
1 stop5h 55m
Deal found 8/12![Delta logo]()
$135
Find flight deals from Chicago to Big Sky
Keep the following information in mind while searching for Chicago to Big Sky flight deals. Data was last updated August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (Delta) |
One-way from | $106 (Kiwi.com) |
Popular in | August |
Cheapest in | April |
Average price | $398 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Big Sky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2026.
Use the filters below to find and compare flights from Chicago to Big Sky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Sat 9/19
12:29 pm-10:31 pm
2 stops11h 02m
Bozeman Gallatin Field
Sat 9/26
8:25 am-6:00 pm
1 stop8h 35m
$313
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Thu 10/22
4:45 pm-7:12 pm
Nonstop3h 27m
Bozeman Gallatin Field
Sun 10/25
8:00 am-12:02 pm
Nonstop3h 02m
$315
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Sat 10/17
4:45 pm-7:12 pm
Nonstop3h 27m
Bozeman Gallatin Field
Tue 10/20
12:53 pm-5:00 pm
Nonstop3h 07m
$315
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Tue 9/15
3:52 pm-10:59 pm
1 stop8h 07m
Bozeman Gallatin Field
Wed 9/23
2:21 pm-11:59 pm
1 stop8h 38m
$335
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Wed 2/10
1:55 pm-10:21 pm
2 stops9h 26m
Bozeman Gallatin Field
Sun 2/14
3:40 pm-11:46 pm
1 stop7h 06m
$340
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Sun 1/24
6:59 pm-12:10 am
1 stop6h 11m
Bozeman Gallatin Field
Thu 1/28
6:00 am-6:40 pm
2 stops11h 40m
$340
ChicagoBozeman
MDW Chicago Midway - BZN Bozeman Gallatin Field
MDWBZN
Chicago Midway
Sun 1/24
12:30 pm-12:10 am
2 stops12h 40m
Bozeman Gallatin Field
Thu 1/28
6:00 am-11:51 am
1 stop4h 51m
$340
ChicagoBozeman
MDW Chicago Midway - BZN Bozeman Gallatin Field
MDWBZN
Chicago Midway
Thu 10/22
2:45 pm-11:20 pm
2 stops9h 35m
Bozeman Gallatin Field
Mon 10/26
4:15 pm-12:15 am
1 stop7h 00m
$344
ChicagoBozeman
MDW Chicago Midway - BZN Bozeman Gallatin Field
MDWBZN
Chicago Midway
Sat 10/17
6:35 am-1:50 pm
2 stops8h 15m
Bozeman Gallatin Field
Tue 10/20
6:30 am-4:40 pm
2 stops9h 10m
$345
Quickest round-trip
ChicagoBozeman
ORD Chicago O'Hare Intl - BZN Bozeman Gallatin Field
ORDBZN
Chicago O'Hare Intl
Fri 12/11
9:10 am-11:33 am
Nonstop3h 23m
Bozeman Gallatin Field
Sun 12/13
12:30 pm-4:30 pm
Nonstop3h 00m
$352
Showing 1-10 of 43 resultsSorted by cheapest first
Best time to book a flight from Chicago to Big Sky
Have a flexible travel schedule? Discover the best time to fly to Big Sky from Chicago with our price prediction graph.
ORD-BZN
MDW-BZN
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 Big Sky
CHI-BS1
ORD-BZN
MDW-BZN
What is the cheapest time of day to fly from CHI to BS1?
Find hourly flight availability from Chicago to Big Sky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2026.
It’s typically best to fly out from Chicago to Big Sky in the evening. Doing so could potentially save you 25% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Chicago to Big Sky
Explore weekly flight availability from Chicago to Big Sky. 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 August 17, 2026.
The most flights from CHI to BS1 are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago to Big Sky?
Airfare is below average for this route at the moment.
Chicago to Big Sky flights typically cost between $330 and $487 in October.The cheapest round-trip price found within the last 5 days was $298 on Delta (Oct 9-Oct 18).
Reviews of airlines servicing Big Sky
Get insights into the airlines that provide service to Big Sky. 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 Big Sky. Reviews last updated August 17, 2026.
See what other customers who have flown with Southwest,Alaska Airlines, andDelta from Chicago to Big Sky have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Big Sky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Big Sky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Big Sky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Big Sky by cabin class
Find flights from Chicago to Big Sky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Big Sky flights
Browse other Chicago and Big Sky flight options. Last updated on August 17, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Big Sky
Discover the top 5 airlines that operate flights from Chicago to Big Sky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$372 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$383 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$269 | Average$412 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$305 | Average$401 | FlexibilityNo cancel fee | On-time75% |