$101+ Cheap flights from South Dakota to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Sep 15 — Sep 221
Round-trip
1 adult, Economy
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Find cheap flights from South Dakota 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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Cheapest flights from South Dakota to ChicagoExplore the most affordable flight options available from South Dakota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2026.
Explore the most affordable flight options available from South Dakota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2026.
This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:52 pm -
1 stop27h 31m
Mon 9/146:30 am -
1 stop13h 37m
Deal found 8/12![Frontier logo]()
$190
This CheapOair deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:52 pm -
1 stop27h 31m
Mon 9/216:30 am -
1 stop13h 37m
Deal found 8/13![Frontier logo]()
$224
This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:48 pm -
1 stop13h 13m
Sun 11/810:40 pm -
1 stop21h 13m
Deal found 8/12![Frontier logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:39 pm -
Nonstop2h 01m
Sun 10/119:40 am -
Nonstop1h 54m
Deal found 8/11![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:57 pm -
1 stop6h 45m
Sun 9/610:35 pm -
Nonstop1h 50m
Deal found 8/11![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:07 pm -
Nonstop2h 38m
Sun 9/279:40 am -
Nonstop2h 35m
Deal found 8/11![American Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:23 pm -
Nonstop2h 11m
Sat 9/510:40 pm -
Nonstop1h 50m
Deal found 8/13![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:52 pm -
1 stop27h 31m
Mon 9/286:00 am -
2 stops14h 07m
Deal found 8/13![Frontier logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:37 pm -
Nonstop2h 24m
Mon 9/288:47 am -
Nonstop2h 28m
Deal found 8/11![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:05 am -
1 stop3h 43m
Tue 9/297:13 pm -
1 stop3h 38m
Deal found 8/12![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:56 pm -
1 stop6h 18m
Sun 9/206:00 am -
1 stop6h 16m
Deal found 8/11![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:07 pm -
Nonstop2h 38m
Tue 9/293:50 pm -
1 stop6h 33m
Deal found 8/12![American Airlines logo]()
$280
Best flights from South Dakota to ChicagoDiscover carefully curated flight deals from South Dakota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
Discover carefully curated flight deals from South Dakota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:07 pm -
Nonstop2h 38m
Sun 9/279:40 am -
Nonstop2h 35m
Deal found 8/11![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:31 pm -
Nonstop2h 24m
Wed 9/95:00 am -
1 stop5h 27m
Deal found 8/11![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 9/305:05 am -
1 stop3h 25m
Mon 10/58:25 am -
1 stop3h 54m
Deal found 8/15![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:48 pm -
1 stop5h 09m
Sat 12/126:15 pm -
1 stop4h 53m
Deal found 8/15![United Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:36 pm -
Nonstop2h 24m
Fri 9/188:59 am -
Nonstop2h 26m
Deal found 8/13![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:56 pm -
1 stop6h 37m
Wed 10/75:30 pm -
1 stop3h 57m
Deal found 8/12![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:56 pm -
1 stop3h 23m
Wed 10/75:31 pm -
1 stop3h 56m
Deal found 8/12![Delta logo]()
$412
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:47 am -
Nonstop1h 52m
Thu 9/39:30 pm -
Nonstop1h 52m
Deal found 8/12![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:29 am -
1 stop4h 10m
Sun 11/1510:22 am -
1 stop6h 33m
Deal found 8/14![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:30 pm -
Nonstop2h 33m
Sun 11/88:40 am -
Nonstop2h 51m
Deal found 8/13![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:47 am -
Nonstop1h 52m
Mon 9/79:30 pm -
Nonstop1h 52m
Deal found 8/13![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:30 am -
1 stop3h 17m
Sat 10/311:27 pm -
2 stops6h 05m
Deal found 8/14![Delta logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:40 am -
Nonstop1h 57m
Wed 11/117:00 am -
1 stop5h 35m
Deal found 8/15![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 10/1411:00 am -
1 stop5h 40m
Sat 10/177:00 am -
2 stops9h 00m
Deal found 8/15![Delta logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:36 pm -
Nonstop2h 24m
Mon 9/145:00 am -
1 stop5h 27m
Deal found 8/13![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:56 pm -
1 stop6h 51m
Wed 9/23:51 pm -
1 stop3h 43m
Deal found 8/14![Delta logo]()
$482
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 10/216:39 am -
1 stop4h 01m
Sun 10/257:00 am -
2 stops9h 58m
Deal found 8/15![Delta logo]()
$565
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:22 am -
1 stop5h 37m
Wed 9/91:30 pm -
1 stop5h 22m
Deal found 8/15![United Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2710:58 am -
1 stop5h 52m
Wed 12/3011:20 am -
1 stop4h 30m
Deal found 8/11![Delta logo]()
$577
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:47 am -
Nonstop1h 52m
Fri 8/289:25 pm -
2 stops18h 58m
Deal found 8/11![United Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 10/216:39 am -
1 stop4h 08m
Sun 10/2510:01 am -
1 stop6h 57m
Deal found 8/15![Delta logo]()
$589
This United Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:33 pm -
2 stops16h 47m
Sun 9/135:00 am -
1 stop5h 44m
Deal found 8/14![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:00 am -
2 stops8h 08m
Sun 8/306:00 am -
1 stop6h 38m
Deal found 8/12![Delta logo]()
$594
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 9/21:26 pm -
2 stops7h 04m
Sun 9/66:00 am -
1 stop6h 38m
Deal found 8/15![Delta logo]()
$598
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/277:40 am -
Nonstop1h 59m
Wed 12/302:40 pm -
1 stop5h 21m
Deal found 8/11![United Airlines logo]()
$615
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:23 am -
1 stop4h 57m
Sat 9/197:13 pm -
1 stop3h 38m
Deal found 8/13![Delta logo]()
$634
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:05 am -
2 stops5h 54m
Thu 9/31:51 pm -
1 stop5h 38m
Deal found 8/11![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:30 am -
1 stop3h 09m
Fri 10/161:55 pm -
2 stops9h 27m
Deal found 8/14![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 8/15. 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 9/295:05 am -
2 stops7h 34m
Sat 10/31:19 pm -
2 stops6h 24m
Deal found 8/15![Delta logo]()
$655
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:36 pm -
1 stop6h 00m
Fri 10/166:20 am -
1 stop3h 52m
Deal found 8/13![Delta logo]()
$667
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated August 16, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated August 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:12 pm -
Nonstop1h 59m
Mon 8/2410:40 pm -
Nonstop1h 50m
Deal found 8/12![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/11![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:21 pm -
Nonstop2h 39m
Tue 9/19:40 am -
1 stop7h 54m
Deal found 8/13![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:31 pm -
Nonstop2h 24m
Sat 9/55:51 pm -
1 stop5h 37m
Deal found 8/13![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 9/25:00 am -
1 stop3h 39m
Sun 9/64:52 pm -
1 stop5h 59m
Deal found 8/15![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:48 pm -
1 stop5h 11m
Tue 9/155:00 am -
1 stop5h 27m
Deal found 8/11![United Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:06 pm -
1 stop6h 12m
Tue 9/155:00 am -
1 stop5h 47m
Deal found 8/11![American Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:07 pm -
Nonstop2h 38m
Tue 9/293:50 pm -
1 stop6h 33m
Deal found 8/12![American Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:37 pm -
Nonstop2h 24m
Mon 9/288:47 am -
Nonstop2h 28m
Deal found 8/11![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:07 pm -
Nonstop2h 38m
Mon 9/286:00 am -
1 stop7h 17m
Deal found 8/11![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:07 pm -
Nonstop2h 38m
Sun 9/279:40 am -
Nonstop2h 35m
Deal found 8/11![American Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:05 am -
1 stop3h 43m
Tue 9/297:13 pm -
1 stop3h 38m
Deal found 8/12![Delta logo]()
$279
One-way flights from South Dakota to ChicagoSearch for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
Search for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:52 pm -
1 stop27h 31m
Deal found 8/11![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:48 pm -
1 stop13h 13m
Deal found 8/13![Frontier logo]()
$112
This Jetabroad deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:56 pm -
1 stop16h 40m
Deal found 8/13![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:52 pm -
1 stop27h 31m
Deal found 8/12![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:31 pm -
1 stop28h 53m
Deal found 8/14![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Mon 11/168:48 pm -
1 stop13h 13m
Deal found 8/15![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:36 pm -
1 stop16h 02m
Deal found 8/14![Multiple Airlines logo]()
$127
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 8/13![United Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:55 am -
2 stops37h 04m
Deal found 8/12![Multiple Airlines logo]()
$133
This Jetabroad deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:56 pm -
1 stop16h 40m
Deal found 8/11![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:06 pm -
1 stop22h 51m
Deal found 8/13![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/2512:29 pm -
2 stops35h 30m
Deal found 8/15![Multiple Airlines logo]()
$148
Find flight deals from South Dakota to Chicago
Keep the following information in mind while searching for South Dakota to Chicago flight deals. Data was last updated August 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (CheapOair) |
One-way from | $101 (CheapOair) |
Popular in | November |
Cheapest in | January |
Average price | $249 |
Good round-trip deal | $343 or less |
Good one-way deal | $308 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from South Dakota to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 16, 2026.
Use the filters below to find and compare flights from South Dakota 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
Sat 9/26
6:07 pm-9:45 pm
Nonstop2h 38m
Chicago O'Hare Intl
Sun 9/27
9:40 am-11:15 am
Nonstop2h 35m
$271
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 9/2
1:31 pm-4:55 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 9/9
5:00 am-9:27 am
1 stop5h 27m
$289
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Wed 9/30
5:05 am-8:30 am
1 stop3h 25m
Chicago O'Hare Intl
Mon 10/5
8:25 am-12:19 pm
1 stop3h 54m
$294
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 12/9
5:48 pm-11:57 pm
1 stop5h 09m
Chicago O'Hare Intl
Sat 12/12
6:15 pm-10:08 pm
1 stop4h 53m
$361
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 9/11
1:36 pm-5:00 pm
Nonstop2h 24m
Chicago O'Hare Intl
Fri 9/18
8:59 am-10:25 am
Nonstop2h 26m
$369
Quickest round-trip
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Mon 8/31
7:47 am-9:39 am
Nonstop1h 52m
Chicago O'Hare Intl
Thu 9/3
9:30 pm-11:22 pm
Nonstop1h 52m
$387
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Thu 11/5
1:30 pm-5:03 pm
Nonstop2h 33m
Chicago O'Hare Intl
Sun 11/8
8:40 am-10:31 am
Nonstop2h 51m
$399
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 9/4
7:47 am-9:39 am
Nonstop1h 52m
Chicago O'Hare Intl
Mon 9/7
9:30 pm-11:22 pm
Nonstop1h 52m
$404
AberdeenChicago
ABR Aberdeen - ORD Chicago O'Hare Intl
ABRORD
Aberdeen
Fri 10/2
2:56 pm-9:33 pm
1 stop6h 37m
Chicago O'Hare Intl
Wed 10/7
5:30 pm-9:27 pm
1 stop3h 57m
$412
AberdeenChicago
ABR Aberdeen - MDW Chicago Midway
ABRMDW
Aberdeen
Fri 10/2
2:56 pm-6:19 pm
1 stop3h 23m
Chicago Midway
Wed 10/7
5:31 pm-9:27 pm
1 stop3h 56m
$412
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from South Dakota to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from South Dakota with our price prediction graph.
FSD-ORD
RAP-ORD
FSD-MDW
ABR-ORD
ABR-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 South Dakota to Chicago
USSD-CHI
FSD-ORD
RAP-ORD
FSD-MDW
ABR-ORD
What is the cheapest month to book a flight from South Dakota to Chicago?
Currently, November is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $246). Flying from South Dakota to Chicago in June is currently the most expensive (average of $347). 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 SD to CHI?
Find hourly flight availability from South Dakota to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 16, 2026.
One of the essential ways to save on airfare from South Dakota to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 25% on airfare.
Weekly flight availability from South Dakota to Chicago
Explore weekly flight availability from South Dakota to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 16, 2026.
The most flights from USSD to CHI are scheduled on a Monday (18 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from South Dakota to Chicago?
Airfare is below average for this route at the moment.
South Dakota to Chicago flights typically cost between $249 and $361 in September.The cheapest round-trip price found within the last 5 days was $190 on Frontier (Sep 11-Sep 14).
How far ahead should I book a flight from South Dakota to Chicago?
Booking 45 days in advance of your planned departure date is, on average, the best time to get cheap flights from South Dakota to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from South Dakota to Chicago?
Use this chart to determine the cheapest time to fly round-trip from South Dakota to Chicago. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their South Dakota to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from South Dakota 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
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Alternative routes for South Dakota to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 16, 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 South Dakota to Chicago by cabin class
Find flights from South Dakota to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
South Dakota and Chicago flights
Browse other South Dakota and Chicago flight options. Last updated on August 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
South Dakota to Chicago flights
Consider these flights traveling from South Dakota to Chicago.
Top 2 airlines flying from South Dakota to Chicago
Discover the top 2 airlines that operate flights from South Dakota to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$285 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$327 | FlexibilityNo cancel fee | On-time69% |