$143+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BZN
Aug 1 — Aug 81
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 61 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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Best
Last-minute
One-way
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 July 2, 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 July 2, 2026.
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:15 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Tue 8/184:32 pm
BZN
- ORD
1 stop6h 27m
United Airlines
Deal found 7/1![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
MDW
- BZN
1 stop9h 35m
Southwest
Thu 8/2712:20 pm
BZN
- MDW
Nonstop2h 55m
Southwest
Deal found 7/1![Southwest logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 8/145:00 am
ORD
- BZN
1 stop7h 05m
American Airlines
Fri 8/2112:55 pm
BZN
- ORD
Nonstop3h 21m
American Airlines
Deal found 6/30![American Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:45 am
ORD
- BZN
Nonstop3h 20m
American Airlines
Sun 8/234:15 pm
BZN
- ORD
1 stop7h 03m
American Airlines
Deal found 7/2![American Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 6/29. 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 11/1110:50 am
ORD
- BZN
1 stop5h 23m
United Airlines
Wed 11/182:37 pm
BZN
- ORD
1 stop7h 07m
United Airlines
Deal found 6/29![United Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 6/28. 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 8/266:00 pm
MDW
- BZN
1 stop5h 25m
Southwest
Wed 9/22:00 pm
BZN
- MDW
1 stop4h 50m
Southwest
Deal found 6/28![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:01 pm
ORD
- BZN
Nonstop3h 22m
United Airlines
Sat 8/224:30 pm
BZN
- ORD
Nonstop3h 07m
United Airlines
Deal found 7/1![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 6/27. 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 9/95:30 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Wed 9/164:23 pm
BZN
- ORD
Nonstop3h 07m
United Airlines
Deal found 6/27![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:44 pm
ORD
- BZN
1 stop5h 20m
Delta
Wed 8/196:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 7/1![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:21 pm
MDW
- BZN
1 stop7h 36m
Delta
Mon 10/196:00 am
BZN
- MDW
1 stop4h 48m
Delta
Deal found 7/2![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:15 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Wed 8/194:30 pm
BZN
- ORD
Nonstop3h 07m
United Airlines
Deal found 6/30![United Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:15 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Fri 8/75:51 pm
BZN
- ORD
1 stop5h 53m
United Airlines
Deal found 7/1![United Airlines logo]()
$309
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 July 2, 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 July 2, 2026.
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:45 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Wed 8/124:32 pm
BZN
- ORD
1 stop5h 14m
United Airlines
Deal found 7/1![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:44 pm
ORD
- BZN
1 stop5h 20m
Delta
Thu 8/206:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 6/29![Delta logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:31 am
ORD
- BZN
1 stop9h 56m
Alaska Airlines
Wed 11/187:07 pm
BZN
- ORD
1 stop9h 33m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 6/27. 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 8/114:40 pm
MDW
- BZN
2 stops6h 45m
Southwest
Tue 8/186:55 am
BZN
- MDW
1 stop9h 40m
Southwest
Deal found 6/27![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/27. 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 10/34:20 pm
ORD
- BZN
1 stop5h 44m
United Airlines
Wed 10/72:37 pm
BZN
- ORD
1 stop7h 09m
United Airlines
Deal found 6/27![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 6/28. 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 9/47:44 pm
ORD
- BZN
1 stop5h 20m
Delta
Mon 9/76:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 6/28![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:00 am
ORD
- BZN
1 stop5h 39m
United Airlines
Wed 8/124:32 pm
BZN
- ORD
1 stop6h 27m
United Airlines
Deal found 7/1![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 6/30. 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 8/178:28 am
ORD
- BZN
1 stop7h 22m
Delta
Fri 8/216:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 6/30![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:50 am
MDW
- BZN
Nonstop3h 05m
Southwest
Thu 8/2712:20 pm
BZN
- MDW
Nonstop2h 55m
Southwest
Deal found 7/1![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 6/27. 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 9/117:00 am
ORD
- BZN
1 stop8h 37m
Delta
Mon 9/146:00 am
BZN
- ORD
1 stop4h 55m
Delta
Deal found 6/27![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:45 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Sun 10/2512:30 pm
BZN
- ORD
Nonstop3h 00m
United Airlines
Deal found 7/1![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 6/29. 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 8/126:00 pm
MDW
- BZN
1 stop5h 25m
Southwest
Mon 8/175:05 pm
BZN
- MDW
1 stop6h 20m
Southwest
Deal found 6/29![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 6/28. 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 7/287:06 pm
MDW
- BZN
1 stop5h 46m
Delta
Wed 8/511:27 am
BZN
- MDW
1 stop5h 34m
Delta
Deal found 6/28![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:00 am
MDW
- BZN
Nonstop3h 10m
Southwest
Sat 8/224:10 pm
BZN
- MDW
1 stop12h 30m
Southwest
Deal found 7/1![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 6/28. 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 9/251:55 pm
ORD
- BZN
2 stops11h 20m
Delta
Tue 9/298:25 am
BZN
- ORD
1 stop8h 36m
Delta
Deal found 6/28![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 6/27. 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 9/52:15 pm
MDW
- BZN
2 stops8h 00m
Southwest
Fri 9/117:20 am
BZN
- MDW
2 stops8h 45m
Southwest
Deal found 6/27![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 6/30. 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 8/281:25 pm
MDW
- BZN
2 stops11h 39m
Delta
Sat 8/296:19 am
BZN
- MDW
1 stop5h 51m
Delta
Deal found 6/30![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 pm
MDW
- BZN
1 stop5h 25m
Southwest
Wed 8/126:55 am
BZN
- MDW
1 stop7h 10m
Southwest
Deal found 7/1![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 6/28. 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 7/285:54 pm
ORD
- BZN
1 stop6h 58m
Delta
Fri 7/313:54 pm
BZN
- ORD
1 stop6h 44m
Delta
Deal found 6/28![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:20 pm
MDW
- BZN
2 stops8h 05m
Southwest
Fri 10/211:05 am
BZN
- MDW
2 stops9h 05m
Southwest
Deal found 7/1![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:25 pm
MDW
- BZN
1 stop4h 51m
Delta
Thu 8/206:19 am
BZN
- MDW
1 stop5h 51m
Delta
Deal found 6/29![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:25 pm
MDW
- BZN
1 stop13h 10m
Southwest
Thu 7/304:30 pm
BZN
- MDW
1 stop6h 45m
Southwest
Deal found 7/1![Southwest logo]()
$410
This Delta deal was found by Cheapflights users on 6/28. 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 9/117:13 pm
MDW
- BZN
1 stop5h 06m
Delta
Sun 9/136:17 am
BZN
- MDW
1 stop6h 03m
Delta
Deal found 6/28![Delta logo]()
$422
Last-minute flights from Chicago to Big SkyDiscover last-minute flight deals from Chicago to Big Sky. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Big Sky. Data last updated July 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:15 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Fri 8/75:51 pm
BZN
- ORD
1 stop5h 53m
United Airlines
Deal found 7/1![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:00 am
ORD
- BZN
1 stop5h 37m
United Airlines
Fri 8/142:30 pm
BZN
- ORD
1 stop7h 16m
United Airlines
Deal found 7/1![United Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:15 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Tue 8/184:32 pm
BZN
- ORD
1 stop6h 27m
United Airlines
Deal found 7/1![United Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 8/1412:11 pm
ORD
- BZN
1 stop9h 26m
American Airlines
Fri 8/2112:55 pm
BZN
- ORD
Nonstop3h 21m
American Airlines
Deal found 6/30![American Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:44 pm
ORD
- BZN
1 stop5h 20m
Delta
Wed 8/196:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 7/1![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:15 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Wed 8/194:30 pm
BZN
- ORD
Nonstop3h 07m
United Airlines
Deal found 6/30![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:45 am
ORD
- BZN
Nonstop3h 20m
American Airlines
Sun 8/234:15 pm
BZN
- ORD
1 stop7h 03m
American Airlines
Deal found 7/2![American Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:01 pm
ORD
- BZN
Nonstop3h 22m
United Airlines
Sat 8/224:30 pm
BZN
- ORD
Nonstop3h 07m
United Airlines
Deal found 7/1![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:59 am
MDW
- BZN
1 stop5h 51m
Delta
Tue 8/256:19 am
BZN
- MDW
1 stop5h 51m
Delta
Deal found 7/1![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:46 pm
MDW
- BZN
2 stops11h 30m
Delta
Tue 8/256:19 am
BZN
- MDW
1 stop5h 51m
Delta
Deal found 7/1![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
MDW
- BZN
1 stop9h 35m
Southwest
Wed 8/2612:55 pm
BZN
- MDW
Nonstop2h 55m
Southwest
Deal found 7/1![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/28. 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 8/266:00 pm
MDW
- BZN
1 stop5h 25m
Southwest
Wed 9/22:00 pm
BZN
- MDW
1 stop4h 50m
Southwest
Deal found 6/28![Southwest logo]()
$300
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 July 2, 2026.
Search for one-way flight options from Chicago to Big Sky. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:58 am
ORD
- BZN
Nonstop3h 27m
American Airlines
Deal found 7/2![American Airlines logo]()
$143
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:50 am
MDW
- BZN
Nonstop3h 05m
Southwest
Deal found 6/30![Southwest logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:45 am
ORD
- BZN
2 stops32h 21m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:00 pm
ORD
- BZN
1 stop24h 01m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:46 pm
ORD
- BZN
1 stop7h 58m
Delta
Deal found 7/2![Delta logo]()
$153
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:13 pm
MDW
- BZN
1 stop5h 06m
Delta
Deal found 7/2![Delta logo]()
$153
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:03 pm
ORD
- BZN
2 stops9h 34m
Delta
Deal found 7/2![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 6/30. 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 8/281:25 pm
MDW
- BZN
2 stops11h 39m
Delta
Deal found 6/30![Delta logo]()
$158
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:45 pm
ORD
- BZN
Nonstop3h 27m
United Airlines
Deal found 6/30![United Airlines logo]()
$160
This United Airlines deal was found by Cheapflights users on 6/29. 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 8/79:10 am
ORD
- BZN
Nonstop3h 34m
United Airlines
Deal found 6/29![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:00 pm
ORD
- BZN
1 stop25h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 am
ORD
- BZN
1 stop8h 20m
United Airlines
Deal found 6/27![United Airlines logo]()
$168
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 July 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (United Airlines) |
One-way from | $143 (American Airlines) |
Popular in | February |
Cheapest in | April |
Average price | $349 |
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 July 2, 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 - BZN
ORDBZN
Chicago O'Hare Intl
Tue 8/4
12:45 pm-3:13 pm
Nonstop3h 28m
Bozeman Gallatin Field
Wed 8/12
4:32 pm-10:46 pm
1 stop5h 14m
$295
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Sat 10/3
4:20 pm-9:04 pm
1 stop5h 44m
Bozeman Gallatin Field
Wed 10/7
2:37 pm-10:46 pm
1 stop7h 09m
$300
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Thu 8/13
7:44 pm-12:04 am
1 stop5h 20m
Bozeman Gallatin Field
Thu 8/20
6:00 am-11:59 am
1 stop4h 59m
$305
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Fri 9/4
7:44 pm-12:04 am
1 stop5h 20m
Bozeman Gallatin Field
Mon 9/7
6:00 am-11:59 am
1 stop4h 59m
$305
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Wed 8/12
5:00 am-9:39 am
1 stop5h 39m
Bozeman Gallatin Field
Wed 8/12
4:32 pm-11:59 pm
1 stop6h 27m
$305
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Mon 8/17
8:28 am-2:50 pm
1 stop7h 22m
Bozeman Gallatin Field
Fri 8/21
6:00 am-11:59 am
1 stop4h 59m
$305
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Fri 9/11
7:00 am-2:37 pm
1 stop8h 37m
Bozeman Gallatin Field
Mon 9/14
6:00 am-11:55 am
1 stop4h 55m
$305
ChicagoBozeman
MDW - BZN
MDWBZN
Chicago Midway
Tue 7/28
7:06 pm-11:52 pm
1 stop5h 46m
Bozeman Gallatin Field
Wed 8/5
11:27 am-6:01 pm
1 stop5h 34m
$305
ChicagoBozeman
ORD - BZN
ORDBZN
Chicago O'Hare Intl
Fri 9/25
1:55 pm-12:15 am
2 stops11h 20m
Bozeman Gallatin Field
Tue 9/29
8:25 am-6:01 pm
1 stop8h 36m
$310
ChicagoBozeman
MDW - BZN
MDWBZN
Chicago Midway
Fri 8/28
1:25 pm-12:04 am
2 stops11h 39m
Bozeman Gallatin Field
Sat 8/29
6:19 am-1:10 pm
1 stop5h 51m
$310
Showing 1-10 of 45 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 July 2, 2026.
It’s typically best to fly out from Chicago to Big Sky in the evening. Doing so could potentially save you 27% 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 July 2, 2026.
The most flights from CHI to BS1 are scheduled on a Thursday (10 on average). You will have fewer flight options on Saturday, 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 Big Sky?
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 July 2, 2026.
See what other customers who have flown with Alaska Airlines,Southwest, 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.
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Popular flights
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 July 2, 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 July 2, 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 July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$210 | Average$425 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$362 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$242 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$243 | Average$401 | FlexibilityNo cancel fee | On-time75% |