$141+ Cheap flights from Rapid City (RAP) 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
RAP — CHI
Oct 14 — Oct 211
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Rapid City 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 Rapid City to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Rapid City to ChicagoExplore the most affordable flight options available from Rapid City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
Explore the most affordable flight options available from Rapid City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
Nonstop2h 34m
Tue 12/87:50 pm -
Nonstop2h 52m
Deal found 9/10![United Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2112:30 pm -
1 stop6h 00m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 9/9![United Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:07 pm -
Nonstop2h 38m
Sun 10/44:00 pm -
Nonstop2h 37m
Deal found 9/10![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/215:04 pm -
1 stop5h 55m
Wed 10/286:00 am -
1 stop7h 21m
Deal found 9/9![American Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:04 pm -
1 stop5h 55m
Sun 10/256:00 am -
1 stop7h 21m
Deal found 9/10![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:21 am -
1 stop4h 29m
Tue 12/812:39 pm -
1 stop4h 14m
Deal found 9/10![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:37 pm -
Nonstop2h 24m
Tue 10/2710:55 am -
1 stop7h 14m
Deal found 9/12![United Airlines logo]()
$320
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.
Sat 11/146:45 am -
1 stop4h 03m
Wed 11/185:42 pm -
1 stop5h 55m
Deal found 9/13![Delta logo]()
$321
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.
Sat 11/1411:29 am -
1 stop4h 10m
Wed 11/1810:34 am -
1 stop6h 20m
Deal found 9/13![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:47 pm -
1 stop6h 43m
Sat 10/34:00 pm -
Nonstop2h 37m
Deal found 9/10![American Airlines logo]()
$329
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.
Fri 11/134:36 pm -
1 stop3h 57m
Wed 11/189:59 am -
1 stop6h 55m
Deal found 9/13![Delta logo]()
$330
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.
Sat 11/1411:29 am -
1 stop4h 10m
Mon 11/235:29 pm -
1 stop6h 08m
Deal found 9/13![Delta logo]()
$330
Best flights from Rapid City to ChicagoDiscover carefully curated flight deals from Rapid City to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
Discover carefully curated flight deals from Rapid City to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2112:30 pm -
1 stop6h 00m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 9/9![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 1/711:30 am -
1 stop4h 20m
Sat 1/95:35 pm -
1 stop6h 04m
Deal found 9/9![Delta logo]()
$310
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.
Sat 11/146:45 am -
1 stop4h 05m
Fri 11/2010:34 am -
1 stop4h 09m
Deal found 9/13![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:30 pm -
Nonstop2h 33m
Sun 11/228:40 am -
Nonstop2h 51m
Deal found 9/10![United Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:21 am -
1 stop4h 29m
Tue 12/812:39 pm -
1 stop4h 14m
Deal found 9/10![Delta logo]()
$360
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 9/2910:26 am -
1 stop7h 04m
Sat 10/38:40 am -
1 stop4h 46m
Deal found 9/14![United Airlines logo]()
$379
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.
Sun 10/111:37 pm -
Nonstop2h 24m
Sun 10/185:00 am -
1 stop5h 28m
Deal found 9/13![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:17 am -
1 stop8h 05m
Sun 10/258:40 am -
Nonstop2h 37m
Deal found 9/10![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:37 pm -
Nonstop2h 24m
Sun 10/258:40 am -
Nonstop2h 37m
Deal found 9/12![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:45 am -
1 stop4h 05m
Wed 11/1810:34 am -
1 stop4h 09m
Deal found 9/10![Delta logo]()
$549
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:41 pm -
1 stop6h 18m
Mon 9/287:00 am -
1 stop6h 26m
Deal found 9/9![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:29 am -
1 stop4h 18m
Fri 10/3010:12 am -
1 stop6h 46m
Deal found 9/10![Delta logo]()
$577
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 10/131:37 pm -
Nonstop2h 24m
Sat 10/178:47 am -
Nonstop2h 28m
Deal found 9/14![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:39 am -
1 stop4h 08m
Wed 10/2810:12 am -
1 stop6h 46m
Deal found 9/9![Delta logo]()
$580
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.
Tue 10/271:30 pm -
Nonstop2h 33m
Sat 10/318:40 am -
Nonstop2h 51m
Deal found 9/13![United Airlines logo]()
$469
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.
Thu 10/296:39 am -
1 stop4h 08m
Thu 11/510:12 am -
1 stop6h 46m
Deal found 9/13![Delta logo]()
$593
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.
Thu 10/16:48 am -
1 stop5h 32m
Sun 10/47:13 pm -
1 stop4h 05m
Deal found 9/13![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:21 am -
1 stop4h 29m
Sun 12/69:37 am -
2 stops7h 16m
Deal found 9/10![Delta logo]()
$644
Last-minute flights from Rapid City to ChicagoDiscover last-minute flight deals from Rapid City to Chicago. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Rapid City to Chicago. Data last updated September 14, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:47 pm -
1 stop6h 43m
Sat 10/34:00 pm -
Nonstop2h 37m
Deal found 9/10![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:42 am -
1 stop6h 37m
Sat 10/39:59 am -
1 stop6h 52m
Deal found 9/10![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:07 pm -
Nonstop2h 38m
Sun 10/44:00 pm -
Nonstop2h 37m
Deal found 9/10![American Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/135:53 pm -
1 stop5h 06m
Mon 10/198:47 am -
Nonstop2h 28m
Deal found 9/9![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/134:38 pm -
1 stop3h 49m
Sat 10/179:59 am -
1 stop6h 59m
Deal found 9/9![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/134:38 pm -
1 stop3h 49m
Mon 10/196:20 am -
1 stop5h 25m
Deal found 9/9![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2112:30 pm -
1 stop6h 00m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 9/9![United Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:04 pm -
1 stop5h 55m
Wed 10/286:00 am -
1 stop7h 21m
Deal found 9/11![American Airlines logo]()
$321
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:04 pm -
1 stop5h 55m
Sun 10/256:00 am -
1 stop7h 21m
Deal found 9/13![American Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:37 pm -
Nonstop2h 24m
Tue 10/2710:55 am -
1 stop7h 14m
Deal found 9/12![United Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:51 pm -
1 stop8h 19m
Sun 10/256:00 am -
1 stop7h 21m
Deal found 9/11![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:29 am -
1 stop4h 18m
Fri 10/3010:12 am -
1 stop6h 46m
Deal found 9/10![Delta logo]()
$577
One-way flights from Rapid City to ChicagoSearch for one-way flight options from Rapid City to Chicago. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
Search for one-way flight options from Rapid City to Chicago. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:37 pm -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$141
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:04 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:07 am -
2 stops36h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$173
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:00 am -
1 stop5h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:48 pm -
1 stop12h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/185:35 pm -
2 stops35h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/199:19 pm -
2 stops32h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:07 am -
1 stop23h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/812:06 pm -
1 stop16h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:07 am -
2 stops24h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:48 pm -
2 stops21h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:07 am -
2 stops32h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$255
Find flight deals from Rapid City to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Rapid City (RAP) 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 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $290 (United Airlines) |
One-way from | $141 (United Airlines) |
Popular in | January |
Cheapest in | June |
Average price | $324 |
Good round-trip deal | $465 or less |
Good one-way deal | $376 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Rapid City 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 14, 2026.
Use the filters below to find and compare flights from Rapid City to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 3/10
7:05 am-2:34 pm
1 stop6h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$251
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 10/28
4:38 pm-9:27 pm
1 stop3h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Wed 10/28
6:39 am-11:47 am
1 stop4h 08m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Wed 12/2
11:21 am-4:50 pm
1 stop4h 29m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
Quickest round-trip
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Mon 10/19
1:37 pm-5:01 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$269
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Sun 10/18
1:37 pm-5:01 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$269
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Sun 12/13
6:00 am-9:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 3/5
4:00 pm-9:37 pm
1 stop4h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 12/16
6:00 am-9:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Mon 11/9
12:39 pm-8:29 pm
1 stop6h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Rapid City 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 Rapid City 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 Rapid City-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rapid City-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rapid City-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Rapid City-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 Rapid City-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 Rapid City to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Rapid City with our price prediction graph.
RAP-CHI
RAP-ORD
RAP-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 Rapid City to Chicago
RAP-CHI
RAP-ORD
RAP-MDW
What is the cheapest month to book a flight from Rapid City to Chicago?
Currently, April is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $209). Flying from Rapid City to Chicago in January is currently the most expensive (average of $536). 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 RAP to CHI?
Find hourly flight availability from Rapid City 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 14, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Rapid City to Chicago as you normally would.
Weekly flight availability from Rapid City to Chicago
Explore weekly flight availability from Rapid City 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 14, 2026.
The most flights from RAP to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Rapid City to Chicago?
Airfare is below average for this route at the moment.
Rapid City to Chicago flights typically cost between $315 and $400 in December.The cheapest round-trip price found within the last 5 days was $290 on United Airlines (Dec 3-Dec 8).
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 14, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Rapid City to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Rapid City to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Rapid City
Popular flights
Alternative routes for Rapid City 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 September 14, 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 Rapid City to Chicago by cabin class
Find flights from Rapid City to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Rapid City and Chicago flights
Browse other Rapid City and Chicago flight options. Last updated on September 14, 2026.
Other flights from Rapid City
Browse through other flights departing from Rapid City. Flights are based on user searches made on Cheapflights and were last updated on September 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Rapid City to Chicago
Discover the top 2 airlines that operate flights from Rapid City 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$306 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$324 | FlexibilityNo cancel fee | On-time69% |