$99+ Cheap flights from Montana to Chicago (CHI)
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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
BZN — CHI
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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Cheapest flights from Montana to ChicagoExplore the most affordable flight options available from Montana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
Explore the most affordable flight options available from Montana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/242:30 pm -
1 stop8h 20m
Mon 9/2810:50 am -
Nonstop3h 05m
Deal found 8/10![Southwest logo]()
$199
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.
Wed 10/143:34 pm -
1 stop7h 00m
Sat 10/177:35 am -
1 stop5h 32m
Deal found 8/12![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:25 am -
2 stops12h 35m
Wed 10/141:55 pm -
2 stops11h 32m
Deal found 8/10![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/234:15 pm -
1 stop5h 00m
Mon 10/266:05 am -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:17 am -
1 stop6h 03m
Mon 10/57:13 pm -
1 stop5h 06m
Deal found 8/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:00 am -
1 stop4h 55m
Tue 10/66:20 am -
1 stop7h 03m
Deal found 8/10![Delta logo]()
$237
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 10/233:34 pm -
1 stop7h 00m
Tue 10/277:35 am -
1 stop5h 32m
Deal found 8/12![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:17 am -
1 stop6h 03m
Tue 10/612:45 pm -
2 stops12h 42m
Deal found 8/10![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/303:38 pm -
1 stop7h 19m
Mon 10/51:55 pm -
2 stops10h 24m
Deal found 8/10![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:25 am -
2 stops12h 35m
Mon 10/262:03 pm -
2 stops9h 34m
Deal found 8/10![Delta logo]()
$247
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.
Fri 10/234:15 pm -
1 stop5h 00m
Tue 10/276:05 am -
1 stop7h 35m
Deal found 8/12![Southwest logo]()
$250
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 10/235:30 am -
1 stop5h 25m
Fri 10/237:15 pm -
1 stop6h 12m
Deal found 8/12![Delta logo]()
$261
Best flights from Montana to ChicagoDiscover carefully curated flight deals from Montana to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
Discover carefully curated flight deals from Montana to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/247:20 am -
2 stops8h 40m
Mon 9/286:15 am -
1 stop9h 35m
Deal found 8/11![Southwest logo]()
$215
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.
Thu 10/221:12 pm -
1 stop7h 48m
Tue 10/275:27 am -
1 stop8h 54m
Deal found 8/12![Delta logo]()
$217
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:07 pm -
1 stop6h 52m
Tue 9/295:00 am -
1 stop5h 46m
Deal found 8/14![United Airlines logo]()
$281
This Alaska Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Sat 11/72:02 pm -
1 stop8h 57m
Tue 11/107:00 am -
1 stop9h 27m
Deal found 8/11![Alaska Airlines logo]()
$369
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 10/233:34 pm -
1 stop7h 00m
Tue 10/276:30 am -
2 stops12h 20m
Deal found 8/12![Delta logo]()
$244
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.
Mon 1/256:00 am -
1 stop4h 51m
Tue 1/2612:30 pm -
2 stops10h 51m
Deal found 8/12![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/132:37 pm -
1 stop7h 09m
Mon 11/164:20 pm -
1 stop6h 10m
Deal found 8/10![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 12/16:45 am -
1 stop6h 25m
Wed 12/98:05 am -
1 stop7h 45m
Deal found 8/10![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/124:32 pm -
1 stop6h 27m
Sun 9/205:00 am -
1 stop5h 39m
Deal found 8/10![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/231:12 pm -
2 stops9h 40m
Sun 10/257:00 am -
1 stop8h 58m
Deal found 8/11![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/107:20 am -
2 stops8h 40m
Wed 9/162:40 pm -
2 stops8h 50m
Deal found 8/10![Southwest logo]()
$352
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.
Fri 9/43:58 pm -
Nonstop3h 42m
Sun 9/135:00 am -
1 stop6h 09m
Deal found 8/12![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/271:35 pm -
2 stops8h 45m
Tue 9/12:40 pm -
2 stops8h 45m
Deal found 8/10![Southwest logo]()
$353
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:45 pm -
1 stop8h 55m
Sat 10/249:00 am -
1 stop14h 59m
Deal found 8/13![Alaska Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/172:31 pm -
1 stop8h 28m
Sun 9/204:00 pm -
Nonstop4h 04m
Deal found 8/11![United Airlines logo]()
$329
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 9/55:20 am -
1 stop5h 39m
Sat 9/128:05 am -
2 stops13h 02m
Deal found 8/12![Delta logo]()
$334
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:32 pm -
1 stop6h 27m
Sun 9/205:00 am -
1 stop5h 39m
Deal found 8/14![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/306:23 am -
1 stop5h 57m
Mon 10/57:13 pm -
1 stop5h 02m
Deal found 8/11![Delta logo]()
$341
This Alaska Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 12/82:10 pm -
1 stop8h 49m
Sat 12/129:20 am -
2 stops15h 39m
Deal found 8/11![Alaska Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/262:00 pm -
1 stop4h 50m
Sun 8/3010:25 am -
Nonstop3h 10m
Deal found 8/11![Southwest logo]()
$401
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 12/258:00 am -
1 stop5h 57m
Tue 1/56:00 am -
2 stops7h 36m
Deal found 8/14![Delta logo]()
$344
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 10/75:19 pm -
1 stop5h 40m
Sun 10/118:42 am -
Nonstop3h 42m
Deal found 8/12![United Airlines logo]()
$352
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:26 pm -
1 stop11h 14m
Mon 10/197:16 pm -
1 stop22h 33m
Deal found 8/14![Alaska Airlines logo]()
$489
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.
Sat 9/52:35 pm -
1 stop5h 15m
Mon 9/710:50 am -
Nonstop3h 05m
Deal found 8/12![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/295:30 am -
2 stops10h 17m
Mon 11/212:27 pm -
1 stop8h 27m
Deal found 8/10![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/511:43 am -
Nonstop3h 05m
Tue 9/85:00 am -
1 stop5h 41m
Deal found 8/11![United Airlines logo]()
$367
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.
Thu 9/172:30 pm -
1 stop8h 20m
Sun 9/206:10 am -
1 stop10h 15m
Deal found 8/14![Southwest logo]()
$414
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.
Thu 11/121:00 pm -
2 stops7h 34m
Mon 11/165:13 pm -
2 stops7h 56m
Deal found 8/14![Delta logo]()
$345
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/272:40 pm -
1 stop5h 33m
Sat 1/306:00 am -
1 stop8h 13m
Deal found 8/14![United Airlines logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/255:18 pm -
2 stops13h 10m
Sat 9/262:22 pm -
2 stops27h 19m
Deal found 8/11![Alaska Airlines logo]()
$550
Last-minute flights from Montana to ChicagoDiscover last-minute flight deals from Montana to Chicago. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Montana to Chicago. Data last updated August 15, 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.
Thu 9/108:25 am -
1 stop8h 36m
Mon 9/147:40 pm -
1 stop5h 39m
Deal found 8/13![Delta logo]()
$279
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 9/113:38 pm -
1 stop7h 19m
Mon 9/147:40 pm -
1 stop5h 39m
Deal found 8/12![Delta logo]()
$239
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 9/158:25 am -
1 stop8h 36m
Sat 9/192:05 pm -
2 stops9h 44m
Deal found 8/13![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/242:30 pm -
1 stop8h 20m
Mon 9/2810:50 am -
Nonstop3h 05m
Deal found 8/10![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/258:25 am -
1 stop8h 36m
Sat 9/268:25 am -
2 stops9h 47m
Deal found 8/11![Delta logo]()
$244
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 9/268:25 am -
1 stop8h 35m
Sat 10/36:40 am -
1 stop7h 58m
Deal found 8/12![Delta logo]()
$217
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.
Sun 9/279:49 pm -
2 stops25h 34m
Wed 9/301:21 pm -
1 stop25h 29m
Deal found 8/14![Multiple Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:17 am -
1 stop6h 03m
Mon 10/57:13 pm -
1 stop5h 06m
Deal found 8/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:00 am -
1 stop4h 55m
Tue 10/66:20 am -
1 stop7h 03m
Deal found 8/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:17 am -
1 stop6h 03m
Tue 10/612:45 pm -
2 stops12h 42m
Deal found 8/10![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/306:55 am -
1 stop10h 05m
Tue 10/66:05 am -
1 stop7h 35m
Deal found 8/10![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/302:00 pm -
2 stops7h 25m
Mon 10/56:05 am -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$277
One-way flights from Montana to ChicagoSearch for one-way flight options from Montana to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Montana to Chicago. Find affordable one-way fares based on user searches. Data last updated August 15, 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.
Mon 9/288:46 pm -
1 stop31h 52m
Deal found 8/12![Multiple Airlines logo]()
$99
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 11/94:05 pm -
1 stop4h 55m
Deal found 8/11![Southwest logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:43 pm -
1 stop31h 55m
Deal found 8/11![Multiple Airlines logo]()
$108
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 11/102:31 pm -
1 stop7h 25m
Deal found 8/12![Delta logo]()
$109
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 10/138:25 am -
1 stop7h 28m
Deal found 8/12![Delta logo]()
$109
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.
Mon 11/98:18 pm -
1 stop8h 17m
Deal found 8/12![Multiple Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/101:35 pm -
2 stops8h 55m
Deal found 8/11![Southwest logo]()
$110
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.
Sun 11/812:46 pm -
1 stop22h 11m
Deal found 8/12![Multiple Airlines logo]()
$110
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 10/224:15 pm -
1 stop7h 00m
Deal found 8/12![Southwest logo]()
$111
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.
Sun 9/279:42 pm -
1 stop30h 56m
Deal found 8/14![Multiple Airlines logo]()
$115
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 10/2911:05 am -
2 stops9h 05m
Deal found 8/12![Southwest logo]()
$116
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.
Sun 9/139:49 pm -
1 stop30h 49m
Deal found 8/14![Multiple Airlines logo]()
$116
Find flight deals from Montana to Chicago
Keep the following information in mind while searching for Montana to Chicago flight deals. Data was last updated August 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Southwest) |
One-way from | $99 (Kiwi.com) |
Popular in | May |
Cheapest in | January |
Average price | $374 |
Good round-trip deal | $430 or less |
Good one-way deal | $246 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Montana 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 2,558,603 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from Montana to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BozemanChicago
BZN Bozeman Gallatin Field - MDW Chicago Midway
BZNMDW
Bozeman Gallatin Field
Thu 9/24
7:20 am-5:00 pm
2 stops8h 40m
Chicago Midway
Mon 9/28
6:15 am-2:50 pm
1 stop9h 35m
$215
BozemanChicago
BZN Bozeman Gallatin Field - ORD Chicago O'Hare Intl
BZNORD
Bozeman Gallatin Field
Thu 10/22
1:12 pm-10:00 pm
1 stop7h 48m
Chicago O'Hare Intl
Tue 10/27
5:27 am-1:21 pm
1 stop8h 54m
$217
BozemanChicago
BZN Bozeman Gallatin Field - ORD Chicago O'Hare Intl
BZNORD
Bozeman Gallatin Field
Fri 10/23
3:34 pm-11:34 pm
1 stop7h 00m
Chicago O'Hare Intl
Tue 10/27
6:30 am-5:50 pm
2 stops12h 20m
$244
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Tue 9/15
4:07 pm-11:59 pm
1 stop6h 52m
Chicago O'Hare Intl
Tue 9/29
5:00 am-9:46 am
1 stop5h 46m
$281
BozemanChicago
BZN Bozeman Gallatin Field - MDW Chicago Midway
BZNMDW
Bozeman Gallatin Field
Mon 1/25
6:00 am-11:51 am
1 stop4h 51m
Chicago Midway
Tue 1/26
12:30 pm-10:21 pm
2 stops10h 51m
$281
BozemanChicago
BZN Bozeman Gallatin Field - ORD Chicago O'Hare Intl
BZNORD
Bozeman Gallatin Field
Fri 11/13
2:37 pm-10:46 pm
1 stop7h 09m
Chicago O'Hare Intl
Mon 11/16
4:20 pm-9:30 pm
1 stop6h 10m
$310
BozemanChicago
BZN Bozeman Gallatin Field - MDW Chicago Midway
BZNMDW
Bozeman Gallatin Field
Tue 12/1
6:45 am-2:10 pm
1 stop6h 25m
Chicago Midway
Wed 12/9
8:05 am-2:50 pm
1 stop7h 45m
$312
BozemanChicago
BZN Bozeman Gallatin Field - ORD Chicago O'Hare Intl
BZNORD
Bozeman Gallatin Field
Fri 10/23
1:12 pm-11:52 pm
2 stops9h 40m
Chicago O'Hare Intl
Sun 10/25
7:00 am-2:58 pm
1 stop8h 58m
$313
BozemanChicago
BZN Bozeman Gallatin Field - ORD Chicago O'Hare Intl
BZNORD
Bozeman Gallatin Field
Sat 9/12
4:32 pm-11:59 pm
1 stop6h 27m
Chicago O'Hare Intl
Sun 9/20
5:00 am-9:39 am
1 stop5h 39m
$315
KalispellChicago
FCA Kalispell Glacier Park - ORD Chicago O'Hare Intl
FCAORD
Kalispell Glacier Park
Fri 9/4
3:58 pm-8:40 pm
Nonstop3h 42m
Chicago O'Hare Intl
Sun 9/13
5:00 am-10:09 am
1 stop6h 09m
$329
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Montana to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Montana with our price prediction graph.
BZN-MDW
BZN-ORD
MSO-ORD
BIL-ORD
FCA-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Montana to Chicago
USMT-CHI
BZN-MDW
BZN-ORD
MSO-ORD
BIL-ORD
What is the cheapest month to book a flight from Montana to Chicago?
Currently, January is the cheapest month in which you can book a flight from Montana to Chicago (average of $310). Flying from Montana to Chicago in July is currently the most expensive (average of $440). 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 MT to CHI?
Find hourly flight availability from Montana 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 August 15, 2026.
When flying from Montana 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 Montana to Chicago
Explore weekly flight availability from Montana 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 August 15, 2026.
The most flights from USMT to CHI are scheduled on a Wednesday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Montana to Chicago?
Airfare is below average for this route at the moment.
Montana to Chicago flights typically cost between $311 and $530 in September.The cheapest round-trip price found within the last 5 days was $199 on Southwest (Sep 24-Sep 28).
How far ahead should I book a flight from Montana to Chicago?
The best time to book flights from Montana to Chicago is 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Related info for your journey
Find useful and relevant information for your journey from Montana 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
Lansing
Merrillville
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
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Alternative routes for Montana 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 August 15, 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 Montana to Chicago by cabin class
Find flights from Montana to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Montana and Chicago flights
Browse other Montana and Chicago flight options. Last updated on August 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Montana to Chicago flights
Consider these flights traveling from Montana to Chicago.
Top 4 airlines flying from Montana to Chicago
Discover the top 4 airlines that operate flights from Montana 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 2,558,603 searches. Data last updated August 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$215 | Average$400 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$230 | Average$488 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$350 | Average$467 | FlexibilityNo cancel fee | On-time75% |