$144+ Cheap flights from Billings (BIL) 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
May 21 — May 281
Round-trip
1 adult, Economy
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Find cheap flights from Billings 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
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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 Billings to Chicago
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Cheapest flights from Billings to ChicagoExplore the most affordable flight options available from Billings to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 21, 2026.
Explore the most affordable flight options available from Billings to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 21, 2026.
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/2312:42 pm
BIL
- ORD
Nonstop3h 02m
American Airlines
Sun 5/249:45 am
ORD
- BIL
Nonstop3h 27m
American Airlines
Deal found 4/20![American Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/55:18 am
BIL
- ORD
2 stops10h 41m
Delta
Wed 8/123:50 pm
ORD
- BIL
1 stop7h 47m
Delta
Deal found 4/20![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 11/312:30 pm
BIL
- ORD
Nonstop3h 00m
United Airlines
Wed 11/116:00 am
ORD
- BIL
1 stop8h 13m
United Airlines
Deal found 4/21![United Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
BIL
- ORD
Nonstop2h 51m
American Airlines
Wed 8/129:55 am
ORD
- BIL
Nonstop3h 03m
American Airlines
Deal found 4/16![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:57 pm
BIL
- ORD
1 stop5h 00m
United Airlines
Wed 10/219:00 am
ORD
- BIL
Nonstop3h 21m
United Airlines
Deal found 4/17![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:30 am
BIL
- ORD
1 stop5h 22m
Delta
Sun 5/245:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/19![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/236:30 am
BIL
- ORD
2 stops9h 26m
Delta
Sun 5/245:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/20![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:15 am
BIL
- MDW
1 stop5h 56m
Delta
Mon 8/246:45 pm
MDW
- BIL
1 stop4h 52m
Delta
Deal found 4/16![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:24 am
BIL
- MDW
2 stops10h 34m
Delta
Tue 5/127:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/16![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/96:30 am
BIL
- MDW
2 stops11h 03m
Delta
Wed 5/1310:59 am
MDW
- BIL
2 stops12h 53m
Delta
Deal found 4/21![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/236:30 am
BIL
- MDW
2 stops8h 42m
Delta
Sun 5/247:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/20![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
BIL
- MDW
2 stops11h 03m
Delta
Tue 6/21:59 pm
MDW
- BIL
2 stops9h 53m
Delta
Deal found 4/16![Delta logo]()
$375
Best flights from Billings to ChicagoDiscover carefully curated flight deals from Billings to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 21, 2026.
Discover carefully curated flight deals from Billings to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 21, 2026.
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/96:30 am
BIL
- MDW
1 stop5h 49m
Delta
Wed 5/1310:59 am
MDW
- BIL
2 stops12h 53m
Delta
Deal found 4/21![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:10 pm
BIL
- ORD
1 stop5h 31m
United Airlines
Tue 9/18:40 am
ORD
- BIL
Nonstop3h 22m
United Airlines
Deal found 4/19![United Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
BIL
- MDW
2 stops11h 03m
Delta
Mon 6/17:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/16![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:18 am
BIL
- ORD
1 stop5h 41m
Delta
Mon 7/203:55 pm
ORD
- BIL
2 stops7h 52m
Delta
Deal found 4/17![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 pm
BIL
- ORD
1 stop5h 44m
United Airlines
Sun 6/145:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 4/17![United Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/202:30 pm
BIL
- ORD
1 stop8h 26m
United Airlines
Mon 5/255:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 4/18![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:24 am
BIL
- MDW
1 stop5h 45m
Delta
Mon 7/137:06 pm
MDW
- BIL
1 stop5h 14m
Delta
Deal found 4/19![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
BIL
- MDW
2 stops11h 20m
Delta
Mon 8/241:00 pm
MDW
- BIL
2 stops10h 27m
Delta
Deal found 4/16![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
BIL
- ORD
2 stops10h 03m
Delta
Mon 8/241:35 pm
ORD
- BIL
2 stops10h 02m
Delta
Deal found 4/16![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
BIL
- MDW
1 stop5h 49m
Delta
Sun 5/247:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/19![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/95:30 am
BIL
- ORD
1 stop5h 22m
Delta
Wed 5/132:00 pm
ORD
- BIL
2 stops9h 52m
Delta
Deal found 4/21![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
BIL
- ORD
2 stops10h 35m
Delta
Tue 6/25:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/16![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
BIL
- MDW
2 stops11h 03m
Delta
Tue 6/27:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/16![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:24 am
BIL
- ORD
2 stops11h 05m
Delta
Sun 8/26:12 pm
ORD
- BIL
1 stop6h 08m
Delta
Deal found 4/16![Delta logo]()
$459
Last-minute flights from Billings to ChicagoDiscover last-minute flight deals from Billings to Chicago. Data last updated April 21, 2026 and is based on user searches.
Discover last-minute flight deals from Billings to Chicago. Data last updated April 21, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/282:35 pm
BIL
- ORD
1 stop5h 45m
United Airlines
Wed 5/61:43 pm
ORD
- BIL
1 stop8h 14m
United Airlines
Deal found 4/20![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/285:20 am
BIL
- ORD
1 stop5h 31m
Delta
Wed 5/611:19 am
ORD
- BIL
2 stops12h 05m
Delta
Deal found 4/20![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:24 am
BIL
- MDW
2 stops10h 34m
Delta
Tue 5/127:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/16![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:24 am
BIL
- ORD
2 stops11h 11m
Delta
Tue 5/125:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/16![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/96:30 am
BIL
- MDW
2 stops11h 03m
Delta
Wed 5/1310:59 am
MDW
- BIL
2 stops12h 53m
Delta
Deal found 4/21![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:30 am
BIL
- ORD
1 stop5h 22m
Delta
Sun 5/245:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/19![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/2312:42 pm
BIL
- ORD
Nonstop3h 02m
American Airlines
Sun 5/249:45 am
ORD
- BIL
Nonstop3h 27m
American Airlines
Deal found 4/20![American Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/236:30 am
BIL
- ORD
2 stops9h 26m
Delta
Sun 5/245:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/20![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/236:30 am
BIL
- MDW
2 stops8h 42m
Delta
Sun 5/247:13 pm
MDW
- BIL
1 stop5h 01m
Delta
Deal found 4/20![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:30 am
BIL
- ORD
1 stop4h 17m
Delta
Tue 6/25:41 pm
ORD
- BIL
1 stop6h 33m
Delta
Deal found 4/16![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:25 pm
BIL
- ORD
1 stop7h 24m
United Airlines
Tue 6/25:00 am
ORD
- BIL
1 stop5h 35m
United Airlines
Deal found 4/16![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:23 pm
BIL
- ORD
1 stop9h 14m
American Airlines
Tue 6/29:45 am
ORD
- BIL
Nonstop3h 27m
American Airlines
Deal found 4/16![American Airlines logo]()
$343
One-way flights from Billings to ChicagoSearch for one-way flight options from Billings to Chicago. Find affordable one-way fares based on user searches. Data last updated April 21, 2026.
Search for one-way flight options from Billings to Chicago. Find affordable one-way fares based on user searches. Data last updated April 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/1810:34 am
BIL
- ORD
3 stops56h 58m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:00 am
BIL
- ORD
2 stops37h 48m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/2210:00 am
BIL
- ORD
1 stop18h 32m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:34 am
BIL
- ORD
2 stops35h 27m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:59 am
BIL
- ORD
2 stops37h 43m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:34 am
BIL
- MDW
2 stops34h 28m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:59 am
BIL
- ORD
2 stops29h 11m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:30 am
BIL
- MDW
1 stop5h 49m
Delta
Deal found 4/16![Delta logo]()
$224
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/55:18 am
BIL
- MDW
2 stops12h 07m
Delta
Deal found 4/20![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:15 am
BIL
- MDW
1 stop5h 56m
Delta
Deal found 4/20![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:15 am
BIL
- MDW
2 stops11h 16m
Delta
Deal found 4/17![Delta logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:41 pm
BIL
- MDW
2 stops26h 18m
Allegiant Air
Deal found 4/18![Allegiant Air logo]()
$273
Find flight deals from Billings to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Billings (BIL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $270 (American Airlines) |
One-way from | $144 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $499 |
Good round-trip deal | $593 or less |
Good one-way deal | $239 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Billings 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 April 21, 2026.
Use the filters below to find and compare flights from Billings to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BillingsChicago
BIL - MDW
BILMDW
Billings Logan Intl
Sat 5/9
6:30 am-1:19 pm
1 stop5h 49m
Chicago Midway
Wed 5/13
10:59 am-10:52 pm
2 stops12h 53m
$339
BillingsChicago
BIL - MDW
BILMDW
Billings Logan Intl
Fri 5/29
6:30 am-6:33 pm
2 stops11h 03m
Chicago Midway
Mon 6/1
7:13 pm-11:14 pm
1 stop5h 01m
$369
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Mon 7/13
5:18 am-11:59 am
1 stop5h 41m
Chicago O'Hare Intl
Mon 7/20
3:55 pm-10:47 pm
2 stops7h 52m
$379
BillingsChicago
BIL - MDW
BILMDW
Billings Logan Intl
Tue 7/7
6:24 am-1:09 pm
1 stop5h 45m
Chicago Midway
Mon 7/13
7:06 pm-11:20 pm
1 stop5h 14m
$389
Quickest round-trip
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Sat 8/29
4:10 pm-10:41 pm
1 stop5h 31m
Chicago O'Hare Intl
Tue 9/1
8:40 am-11:02 am
Nonstop3h 22m
$395
BillingsChicago
BIL - MDW
BILMDW
Billings Logan Intl
Thu 8/20
5:45 am-6:05 pm
2 stops11h 20m
Chicago Midway
Mon 8/24
1:00 pm-10:27 pm
2 stops10h 27m
$404
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Thu 8/20
5:45 am-4:48 pm
2 stops10h 03m
Chicago O'Hare Intl
Mon 8/24
1:35 pm-10:37 pm
2 stops10h 02m
$404
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Sat 6/6
6:00 pm-12:44 am
1 stop5h 44m
Chicago O'Hare Intl
Sun 6/14
5:00 am-9:35 am
1 stop5h 35m
$418
BillingsChicago
BIL - MDW
BILMDW
Billings Logan Intl
Sun 5/17
6:30 am-1:19 pm
1 stop5h 49m
Chicago Midway
Sun 5/24
7:13 pm-11:14 pm
1 stop5h 01m
$419
BillingsChicago
BIL - ORD
BILORD
Billings Logan Intl
Wed 5/20
2:30 pm-11:56 pm
1 stop8h 26m
Chicago O'Hare Intl
Mon 5/25
5:00 am-9:35 am
1 stop5h 35m
$424
Showing 1-10 of 30 resultsSorted by cheapest first
Compare providers for flights from Billings to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Billings to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Billings-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Billings-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Billings-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Billings-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Billings-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Billings to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Billings with our price prediction graph.
BIL-CHI
BIL-ORD
BIL-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Billings to Chicago
BIL-CHI
BIL-ORD
BIL-MDW
What is the cheapest month to book a flight from Billings to Chicago?
Currently, July is the cheapest month in which you can book a flight from Billings to Chicago (average of $191). Flying from Billings to Chicago in November is currently the most expensive (average of $299). 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.
How much does it cost to fly round-trip from Billings to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 21, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Billings to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Overall
7.9
Food
7.2
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Billings 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
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Other flights to Chicago
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Billings and Chicago flights
Browse other Billings and Chicago flight options. Last updated on April 21, 2026.
Other flights from Billings
Browse through other flights departing from Billings. Flights are based on user searches made on Cheapflights and were last updated on April 21, 2026.
Popular flight searches
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Top 3 airlines flying from Billings to Chicago
Discover the top 3 airlines that operate flights from Billings 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 April 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$210 | Average$365 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$230 | Average$492 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$399 | FlexibilityNo cancel fee | On-time69% |