$140+ Cheap flights from Billings (BIL) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
Oct 19 — Oct 261
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
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 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 September 19, 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 September 19, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop8h 19m
Wed 10/282:50 pm -
1 stop7h 22m
Deal found 9/14![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 11/32:42 pm -
1 stop7h 04m
Tue 11/105:48 pm -
1 stop5h 42m
Deal found 9/17![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 11/35:20 am -
2 stops11h 27m
Tue 11/107:35 am -
1 stop5h 43m
Deal found 9/17![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/62:28 pm -
1 stop6h 23m
Tue 10/205:00 am -
1 stop5h 46m
Deal found 9/17![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:40 am -
1 stop5h 23m
Tue 12/153:47 pm -
1 stop5h 01m
Deal found 9/15![Delta logo]()
$352
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 9/182:29 pm -
1 stop6h 31m
Mon 9/215:00 am -
1 stop5h 41m
Deal found 9/18![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
1 stop5h 35m
Sat 10/35:30 am -
2 stops13h 23m
Deal found 9/13![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/265:20 am -
2 stops12h 09m
Thu 10/2911:19 am -
2 stops12h 06m
Deal found 9/16![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:28 pm -
Nonstop3h 02m
Tue 9/229:41 am -
Nonstop3h 16m
Deal found 9/14![American Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:40 am -
1 stop5h 23m
Sun 12/67:05 am -
2 stops11h 36m
Deal found 9/15![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:40 am -
2 stops10h 10m
Sun 12/69:37 am -
2 stops9h 04m
Deal found 9/15![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
2 stops12h 13m
Sat 10/32:00 pm -
1 stop7h 07m
Deal found 9/13![Delta logo]()
$390
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 September 19, 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 September 19, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 11/32:42 pm -
1 stop7h 04m
Tue 11/105:48 pm -
1 stop5h 42m
Deal found 9/17![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/166:15 am -
2 stops11h 22m
Tue 3/231:00 pm -
2 stops7h 48m
Deal found 9/14![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/245:45 am -
2 stops9h 52m
Sat 2/276:00 am -
2 stops7h 19m
Deal found 9/18![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
1 stop5h 35m
Sat 10/35:30 am -
2 stops13h 23m
Deal found 9/13![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:42 pm -
1 stop5h 48m
Tue 11/178:40 am -
1 stop5h 49m
Deal found 9/13![United Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/265:20 am -
2 stops12h 09m
Thu 10/2911:19 am -
2 stops12h 06m
Deal found 9/16![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/14. 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 3/162:40 pm -
1 stop5h 33m
Sat 3/274:00 pm -
1 stop5h 51m
Deal found 9/14![United Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
2 stops12h 13m
Sat 10/32:00 pm -
1 stop7h 07m
Deal found 9/13![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:00 pm -
2 stops9h 52m
Fri 1/17:10 am -
1 stop6h 09m
Deal found 9/15![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:32 am -
2 stops9h 30m
Wed 12/163:47 pm -
1 stop5h 01m
Deal found 9/15![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:23 am -
1 stop7h 06m
Wed 10/711:19 am -
2 stops9h 56m
Deal found 9/18![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/166:15 am -
2 stops11h 22m
Thu 3/256:00 am -
2 stops14h 48m
Deal found 9/14![Delta logo]()
$515
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/166:15 am -
1 stop4h 36m
Fri 3/269:55 am -
1 stop10h 53m
Deal found 9/14![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/166:15 am -
1 stop4h 36m
Mon 3/2212:30 pm -
1 stop8h 18m
Deal found 9/14![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 10/66:16 am -
1 stop4h 31m
Tue 10/2010:59 am -
2 stops10h 16m
Deal found 9/17![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:23 am -
1 stop5h 57m
Wed 10/71:27 pm -
2 stops7h 48m
Deal found 9/18![Delta logo]()
$676
This Delta deal was found by Cheapflights users on 9/16. 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 9/306:23 am -
2 stops11h 10m
Sat 10/31:19 pm -
2 stops7h 48m
Deal found 9/16![Delta logo]()
$682
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 10/36:23 am -
2 stops10h 59m
Sun 10/47:13 pm -
1 stop5h 02m
Deal found 9/16![Delta logo]()
$708
Last-minute flights from Billings to ChicagoDiscover last-minute flight deals from Billings to Chicago. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Billings to Chicago. Data last updated September 19, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 9/182:29 pm -
1 stop6h 31m
Mon 9/215:00 am -
1 stop5h 41m
Deal found 9/18![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:13 pm -
1 stop9h 17m
Tue 9/299:41 am -
Nonstop3h 16m
Deal found 9/15![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/16. 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 9/235:20 am -
1 stop5h 35m
Wed 9/301:55 pm -
2 stops9h 39m
Deal found 9/16![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
1 stop5h 35m
Sat 10/35:30 am -
2 stops13h 23m
Deal found 9/13![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 9/13. 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 9/295:20 am -
2 stops12h 13m
Sat 10/32:00 pm -
1 stop7h 07m
Deal found 9/13![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 9/16. 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 9/306:23 am -
1 stop5h 57m
Sat 10/32:00 pm -
1 stop7h 07m
Deal found 9/16![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/24:00 pm -
1 stop5h 46m
Sat 10/310:55 am -
1 stop7h 21m
Deal found 9/16![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:28 pm -
1 stop6h 24m
Sun 10/45:00 am -
1 stop5h 44m
Deal found 9/16![United Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/62:28 pm -
1 stop6h 23m
Tue 10/205:00 am -
1 stop5h 46m
Deal found 9/17![United Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/212:28 pm -
1 stop5h 50m
Fri 10/234:20 pm -
1 stop5h 50m
Deal found 9/16![United Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop8h 19m
Wed 10/282:50 pm -
1 stop7h 22m
Deal found 9/14![American Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/265:20 am -
2 stops12h 09m
Thu 10/2911:19 am -
2 stops12h 06m
Deal found 9/16![Delta logo]()
$364
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 September 19, 2026.
Search for one-way flight options from Billings to Chicago. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/510:20 pm -
1 stop30h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/1612:14 pm -
1 stop15h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/145:15 pm -
1 stop10h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:47 pm -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Mon 10/199:47 pm -
2 stops31h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$170
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:21 pm -
1 stop7h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$176
This Delta deal was found by Cheapflights users on 9/17. 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 11/146:34 am -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:00 pm -
2 stops7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/510:20 pm -
2 stops18h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:22 pm -
2 stops18h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 9/17. 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 10/56:23 am -
1 stop5h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/297:32 pm -
3 stops45h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$577
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $307 (American Airlines) |
One-way from | $140 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $466 |
Good round-trip deal | $504 or less |
Good one-way deal | $328 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 7,457,451 searches. Data last updated September 19, 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 Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Tue 12/15
6:32 am-2:53 pm
1 stop7h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Mon 3/15
2:40 pm-10:44 pm
1 stop7h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Wed 12/16
6:32 am-2:53 pm
1 stop7h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Tue 3/16
12:58 pm-9:53 pm
1 stop7h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Mon 10/12
6:16 am-2:36 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Mon 3/15
12:58 pm-9:53 pm
1 stop7h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
BillingsChicago
BIL Billings Logan Intl - MDW Chicago Midway
BILMDW
Billings Logan Intl
Mon 10/5
10:20 pm-5:46 pm
2 stops18h 26m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
BillingsChicago
BIL Billings Logan Intl - MDW Chicago Midway
BILMDW
Billings Logan Intl
Fri 10/2
10:22 pm-5:51 pm
2 stops18h 29m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$297
BillingsChicago
BIL Billings Logan Intl - ORD Chicago O'Hare Intl
BILORD
Billings Logan Intl
Tue 11/3
2:42 pm-10:46 pm
1 stop7h 04m
Chicago O'Hare Intl
Tue 11/10
5:48 pm-10:30 pm
1 stop5h 42m
$321
BillingsChicago
BIL Billings Logan Intl - MDW Chicago Midway
BILMDW
Billings Logan Intl
Tue 3/16
6:15 am-6:37 pm
2 stops11h 22m
Chicago Midway
Tue 3/23
1:00 pm-7:48 pm
2 stops7h 48m
$331
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 September.
| 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, February is the cheapest month in which you can book a flight from Billings to Chicago (average of $279). Flying from Billings to Chicago in July is currently the most expensive (average of $561). 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 BIL to CHI?
Find hourly flight availability from Billings 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 September 19, 2026.
When flying from Billings 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 Billings to Chicago
Explore weekly flight availability from Billings 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 September 19, 2026.
The most flights from BIL to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Billings to Chicago?
Airfare is below average for this route at the moment.
Billings to Chicago flights typically cost between $369 and $638 in October.The cheapest round-trip price found within the last 5 days was $307 on American Airlines (Oct 24-Oct 28).
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 September 19, 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.
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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
Valparaiso
Hammond
Saint Joseph
Porter
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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 September 19, 2026.
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Billings and Chicago flights
Browse other Billings and Chicago flight options. Last updated on September 19, 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 September 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$492 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$473 | FlexibilityNo cancel fee | On-time71% |