$122+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
BZN — CHI
Jun 6 — Jun 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Montana to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Montana to Chicago
Cheapest
Best
Last-minute
One-way
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 May 7, 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 May 7, 2026.
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:57 pm
BZN
- ORD
1 stop8h 02m
Alaska Airlines
Wed 6/106:00 am
ORD
- BZN
1 stop9h 09m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:51 am
BIL
- ORD
1 stop5h 28m
Delta
Wed 8/126:45 pm
ORD
- BIL
1 stop5h 28m
Delta
Deal found 5/5![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/205:20 am
BIL
- ORD
1 stop5h 40m
Delta
Wed 7/85:54 pm
ORD
- BIL
1 stop6h 26m
Delta
Deal found 5/6![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:00 pm
BZN
- ORD
Nonstop3h 20m
American Airlines
Sun 6/71:30 pm
ORD
- BZN
Nonstop3h 20m
American Airlines
Deal found 5/4![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:25 pm
BZN
- ORD
Nonstop3h 15m
United Airlines
Sat 6/138:19 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Deal found 5/3![United Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Sat 6/65:00 pm
BZN
- ORD
Nonstop3h 20m
American Airlines
Sun 6/71:30 pm
ORD
- BZN
Nonstop3h 20m
American Airlines
Deal found 5/7![American Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:51 am
BIL
- ORD
1 stop5h 28m
Delta
Thu 8/135:57 pm
ORD
- BIL
1 stop6h 16m
Delta
Deal found 5/5![Delta logo]()
$290
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:40 pm
BZN
- ORD
1 stop7h 01m
Alaska Airlines
Wed 9/236:00 am
ORD
- BZN
1 stop9h 46m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/62:30 pm
BZN
- MDW
1 stop8h 15m
Southwest
Mon 8/1010:50 am
MDW
- BZN
Nonstop3h 05m
Southwest
Deal found 5/7![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:10 am
BIL
- MDW
2 stops12h 23m
Delta
Wed 8/127:25 pm
MDW
- BIL
1 stop4h 48m
Delta
Deal found 5/5![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:25 pm
BZN
- ORD
Nonstop3h 15m
United Airlines
Mon 6/155:00 am
ORD
- BZN
1 stop5h 37m
United Airlines
Deal found 5/5![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:10 am
BIL
- ORD
1 stop5h 49m
Delta
Tue 8/118:28 am
ORD
- BIL
2 stops10h 25m
Delta
Deal found 5/5![Delta logo]()
$295
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 May 7, 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 May 7, 2026.
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:24 am
BIL
- ORD
1 stop7h 41m
Delta
Wed 7/295:54 pm
ORD
- BIL
1 stop6h 26m
Delta
Deal found 5/4![Delta logo]()
$271
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:00 am
BZN
- ORD
Nonstop2h 59m
United Airlines
Sun 7/55:00 am
ORD
- BZN
1 stop5h 29m
United Airlines
Deal found 5/3![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:20 am
BZN
- MDW
2 stops8h 40m
Southwest
Sun 8/96:10 am
MDW
- BZN
1 stop10h 15m
Southwest
Deal found 5/5![Southwest logo]()
$310
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/291:25 pm
FCA
- ORD
Nonstop3h 39m
American Airlines
Tue 6/27:02 am
ORD
- FCA
1 stop8h 58m
American Airlines
Deal found 5/7![American Airlines logo]()
$319
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 9/104:13 pm
MSO
- ORD
1 stop6h 46m
Alaska Airlines
Tue 9/153:52 pm
ORD
- MSO
1 stop8h 07m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1911:50 am
BIL
- ORD
1 stop6h 07m
Delta
Wed 7/295:54 pm
ORD
- BIL
1 stop6h 26m
Delta
Deal found 5/5![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/258:00 am
BZN
- ORD
Nonstop2h 59m
United Airlines
Sun 6/285:00 am
ORD
- BZN
1 stop5h 29m
United Airlines
Deal found 5/7![United Airlines logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:15 am
FCA
- ORD
1 stop9h 33m
Alaska Airlines
Sat 6/65:52 pm
ORD
- FCA
1 stop7h 06m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:50 pm
BZN
- MDW
1 stop8h 35m
Southwest
Tue 6/306:40 pm
MDW
- BZN
1 stop7h 05m
Southwest
Deal found 5/2![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/206:00 am
BZN
- MDW
1 stop6h 09m
Delta
Sat 6/279:54 am
MDW
- BZN
1 stop5h 56m
Delta
Deal found 5/6![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/14:20 pm
BZN
- ORD
1 stop5h 29m
United Airlines
Fri 8/78:15 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Deal found 5/2![United Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/113:51 pm
FCA
- ORD
1 stop7h 48m
American Airlines
Mon 6/291:16 pm
ORD
- FCA
Nonstop3h 46m
American Airlines
Deal found 5/4![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/115:15 am
BZN
- ORD
1 stop5h 45m
Delta
Tue 6/166:30 am
ORD
- BZN
1 stop4h 52m
Delta
Deal found 5/6![Delta logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 10/247:45 pm
FCA
- ORD
1 stop9h 35m
Alaska Airlines
Wed 10/286:00 am
ORD
- FCA
1 stop7h 21m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 10/155:45 am
BZN
- MDW
1 stop7h 40m
Southwest
Mon 10/197:25 am
MDW
- BZN
1 stop9h 10m
Southwest
Deal found 5/7![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 5/2. 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 7/712:13 pm
BZN
- ORD
1 stop5h 44m
Delta
Wed 7/157:40 pm
ORD
- BZN
1 stop5h 43m
Delta
Deal found 5/2![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:31 pm
GTF
- ORD
1 stop6h 11m
United Airlines
Tue 8/254:35 pm
ORD
- GTF
1 stop5h 53m
United Airlines
Deal found 5/5![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:50 pm
BZN
- MDW
2 stops9h 45m
Southwest
Tue 7/215:50 pm
MDW
- BZN
2 stops7h 55m
Southwest
Deal found 5/3![Southwest logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/66:52 pm
GTF
- ORD
1 stop10h 28m
Alaska Airlines
Wed 6/106:00 am
ORD
- GTF
1 stop11h 29m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
BZN
- ORD
1 stop4h 45m
Delta
Fri 8/72:12 pm
ORD
- BZN
2 stops10h 04m
Delta
Deal found 5/4![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 pm
BIL
- ORD
1 stop5h 44m
United Airlines
Mon 6/85:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 5/4![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 8/151:00 pm
BZN
- ORD
1 stop7h 20m
Delta
Mon 8/171:48 pm
ORD
- BZN
2 stops11h 16m
Delta
Deal found 5/6![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:00 pm
BIL
- ORD
1 stop5h 44m
United Airlines
Fri 6/195:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 5/3![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:45 am
BZN
- ORD
2 stops10h 03m
Delta
Mon 9/215:20 pm
ORD
- BZN
1 stop7h 33m
Delta
Deal found 5/5![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:25 am
BZN
- ORD
2 stops12h 23m
Delta
Fri 7/177:40 pm
ORD
- BZN
1 stop5h 43m
Delta
Deal found 5/4![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 pm
BIL
- ORD
1 stop5h 44m
United Airlines
Mon 6/85:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 5/5![United Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:09 pm
HLN
- ORD
1 stop12h 11m
Alaska Airlines
Tue 8/46:00 am
ORD
- HLN
1 stop11h 32m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:56 pm
BZN
- ORD
1 stop6h 43m
Delta
Tue 6/162:07 pm
ORD
- BZN
2 stops10h 51m
Delta
Deal found 5/4![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/62:20 pm
HLN
- ORD
1 stop7h 29m
United Airlines
Sat 6/137:05 am
ORD
- HLN
1 stop7h 28m
United Airlines
Deal found 5/7![United Airlines logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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.
Wed 9/25:11 pm
HLN
- ORD
1 stop17h 56m
Alaska Airlines
Sat 9/59:00 am
ORD
- HLN
1 stop8h 34m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$495
Last-minute flights from Montana to ChicagoDiscover last-minute flight deals from Montana to Chicago. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Montana to Chicago. Data last updated May 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:42 pm
BIL
- ORD
Nonstop3h 02m
American Airlines
Sat 5/303:02 pm
ORD
- BIL
1 stop9h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/314:10 pm
BIL
- ORD
1 stop7h 34m
United Airlines
Sat 6/65:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 5/5![United Airlines logo]()
$290
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:57 pm
BZN
- ORD
1 stop8h 02m
Alaska Airlines
Wed 6/106:00 am
ORD
- BZN
1 stop9h 09m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:00 pm
BZN
- ORD
Nonstop3h 20m
American Airlines
Sun 6/71:30 pm
ORD
- BZN
Nonstop3h 20m
American Airlines
Deal found 5/4![American Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Sat 6/65:00 pm
BZN
- ORD
Nonstop3h 20m
American Airlines
Sun 6/71:30 pm
ORD
- BZN
Nonstop3h 20m
American Airlines
Deal found 5/7![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:25 pm
BZN
- ORD
Nonstop3h 15m
United Airlines
Sat 6/138:19 pm
ORD
- BZN
Nonstop3h 28m
United Airlines
Deal found 5/3![United Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:25 pm
BZN
- ORD
Nonstop3h 15m
United Airlines
Mon 6/155:00 am
ORD
- BZN
1 stop5h 37m
United Airlines
Deal found 5/5![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/156:00 am
BZN
- MDW
1 stop6h 09m
Delta
Mon 6/291:49 pm
MDW
- BZN
1 stop6h 56m
Delta
Deal found 5/6![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/205:20 am
BIL
- ORD
1 stop5h 40m
Delta
Wed 7/85:54 pm
ORD
- BIL
1 stop6h 26m
Delta
Deal found 5/6![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:24 am
BIL
- ORD
2 stops9h 34m
Delta
Wed 7/11:40 pm
ORD
- BIL
2 stops10h 20m
Delta
Deal found 5/5![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:10 pm
BZN
- MDW
1 stop9h 15m
Southwest
Sat 7/410:15 am
MDW
- BZN
Nonstop3h 10m
Southwest
Deal found 5/3![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/3011:50 am
BIL
- ORD
1 stop6h 08m
Delta
Fri 7/31:40 pm
ORD
- BIL
2 stops10h 20m
Delta
Deal found 5/6![Delta logo]()
$305
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 May 7, 2026.
Search for one-way flight options from Montana to Chicago. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:30 am
FCA
- ORD
1 stop17h 37m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$122
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 11/38:00 am
BZN
- ORD
1 stop8h 01m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$133
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/246:40 am
BZN
- MDW
Nonstop2h 50m
Southwest
Deal found 5/6![Southwest logo]()
$143
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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.
Sat 7/185:03 pm
BZN
- ORD
Nonstop3h 27m
American Airlines
Deal found 5/6![American Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:37 pm
BZN
- ORD
1 stop7h 07m
United Airlines
Deal found 5/4![United Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/2910:00 am
BIL
- ORD
2 stops33h 43m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/302:35 pm
BZN
- MDW
1 stop6h 50m
Southwest
Deal found 5/6![Southwest logo]()
$153
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 8/66:00 am
BZN
- ORD
1 stop4h 59m
Delta
Deal found 5/6![Delta logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:36 am
FCA
- ORD
2 stops32h 56m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/39:59 am
BIL
- ORD
1 stop18h 08m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/24:48 pm
BZN
- ORD
2 stops36h 31m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:21 pm
BIL
- ORD
Nonstop3h 02m
American Airlines
Deal found 5/4![American Airlines logo]()
$157
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Expedia) |
One-way from | $122 (Kiwi.com) |
Popular in | May |
Cheapest in | September |
Average price | $403 |
Good round-trip deal | $379 or less |
Good one-way deal | $188 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 May 7, 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
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Wed 7/22
6:24 am-3:05 pm
1 stop7h 41m
Chicago O'Hare Intl
Wed 7/29
5:54 pm-11:20 pm
1 stop6h 26m
$271
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Sun 7/19
11:50 am-6:57 pm
1 stop6h 07m
Chicago O'Hare Intl
Wed 7/29
5:54 pm-11:20 pm
1 stop6h 26m
$290
Quickest round-trip
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Thu 7/2
8:00 am-11:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Sun 7/5
5:00 am-9:29 am
1 stop5h 29m
$295
BozemanChicago
BZN - MDW
BZNMDW
Bozeman Gallatin Field
Sat 6/20
6:00 am-1:09 pm
1 stop6h 09m
Chicago Midway
Sat 6/27
9:54 am-2:50 pm
1 stop5h 56m
$305
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Thu 6/11
5:15 am-12:00 pm
1 stop5h 45m
Chicago O'Hare Intl
Tue 6/16
6:30 am-10:22 am
1 stop4h 52m
$305
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Tue 7/7
12:13 pm-6:57 pm
1 stop5h 44m
Chicago O'Hare Intl
Wed 7/15
7:40 pm-12:23 am
1 stop5h 43m
$305
BozemanChicago
BZN - MDW
BZNMDW
Bozeman Gallatin Field
Thu 8/6
7:20 am-5:00 pm
2 stops8h 40m
Chicago Midway
Sun 8/9
6:10 am-3:25 pm
1 stop10h 15m
$310
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Thu 6/25
8:00 am-11:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Sun 6/28
5:00 am-9:29 am
1 stop5h 29m
$310
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Sat 8/1
4:20 pm-10:49 pm
1 stop5h 29m
Chicago O'Hare Intl
Fri 8/7
8:15 pm-10:43 pm
Nonstop3h 28m
$310
BozemanChicago
BZN - ORD
BZNORD
Bozeman Gallatin Field
Sat 8/1
6:00 am-11:45 am
1 stop4h 45m
Chicago O'Hare Intl
Fri 8/7
2:12 pm-11:16 pm
2 stops10h 04m
$310
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.
BIL-ORD
BZN-ORD
BZN-MDW
FCA-ORD
MSO-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
BIL-ORD
BZN-ORD
BZN-MDW
FCA-ORD
How far ahead should I book a flight from Montana to Chicago?
The best time to book flights from Montana to Chicago is 89 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Montana to Chicago?
Currently, July is the cheapest month in which you can book a flight from Montana to Chicago (average of $118). Flying from Montana to Chicago in May is currently the most expensive (average of $248). 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 May 7, 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 May 7, 2026.
The most flights from USMT to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Montana to Chicago?
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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 May 7, 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 May 7, 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 May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$336 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$210 | Average$483 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$435 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$350 | Average$467 | FlexibilityNo cancel fee | On-time75% |