$145+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Oct 1 — Oct 81
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 September 1, 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 September 1, 2026.
This Frontier deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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 8/28![Frontier logo]()
$261
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Mon 10/1210:48 pm -
Nonstop1h 53m
Deal found 8/28![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 12/96:00 am -
Nonstop2h 34m
Wed 12/167:50 pm -
Nonstop2h 52m
Deal found 8/28![United Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/256:41 pm -
Nonstop2h 18m
Sun 9/276:00 am -
1 stop6h 16m
Deal found 8/28![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/145:53 pm -
1 stop5h 06m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 8/31![United Airlines logo]()
$291
This ezTravel 易遊網 deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ezTravel 易遊網 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 8/29![Frontier logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/256:07 pm -
Nonstop2h 38m
Mon 9/284:00 pm -
Nonstop2h 37m
Deal found 8/31![American Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/308:23 am -
1 stop4h 57m
Sat 10/37:13 pm -
1 stop3h 38m
Deal found 8/30![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/136:39 am -
1 stop6h 57m
Sat 10/176:20 am -
1 stop5h 25m
Deal found 8/28![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 12/86:42 am -
1 stop4h 17m
Tue 12/1510:24 am -
1 stop4h 36m
Deal found 8/28![Delta logo]()
$301
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/256:07 pm -
Nonstop2h 38m
Tue 9/294:00 pm -
Nonstop2h 37m
Deal found 8/31![American Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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
Mon 9/2110:39 pm -
Nonstop1h 50m
Deal found 8/30![American Airlines logo]()
$304
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 September 1, 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 September 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/36:31 pm -
Nonstop2h 02m
Sun 10/49:20 pm -
Nonstop1h 51m
Deal found 8/31![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/136:39 am -
1 stop4h 01m
Sat 10/179:59 am -
1 stop6h 59m
Deal found 9/1![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/115:50 pm -
1 stop5h 09m
Sat 11/148:40 am -
Nonstop2h 51m
Deal found 8/28![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/1111:28 am -
1 stop4h 11m
Sat 11/1410:34 am -
1 stop6h 20m
Deal found 8/28![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/135:10 am -
1 stop3h 34m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 8/29![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/164:41 pm -
1 stop5h 05m
Mon 10/198:47 am -
Nonstop2h 28m
Deal found 9/1![United Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/65:50 pm -
1 stop5h 09m
Mon 11/98:40 am -
Nonstop2h 51m
Deal found 9/1![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1211:22 am -
1 stop6h 09m
Wed 9/165:00 am -
1 stop5h 27m
Deal found 8/28![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/117:47 am -
Nonstop1h 52m
Sun 9/139:20 pm -
Nonstop1h 52m
Deal found 9/1![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/281:00 pm -
1 stop3h 40m
Thu 11/51:55 pm -
2 stops9h 27m
Deal found 8/28![Delta logo]()
$484
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 12/116:00 am -
Nonstop2h 34m
Tue 12/157:50 pm -
Nonstop2h 52m
Deal found 8/28![United Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2011:17 am -
1 stop8h 05m
Sat 10/248:47 am -
Nonstop2h 28m
Deal found 8/29![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1110:40 am -
1 stop4h 25m
Tue 9/151:55 pm -
2 stops8h 56m
Deal found 8/27![Delta logo]()
$499
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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
Sat 10/178:47 am -
Nonstop2h 28m
Deal found 8/30![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/911:28 am -
1 stop4h 11m
Wed 11/1112:30 pm -
1 stop4h 24m
Deal found 8/28![Delta logo]()
$521
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/196:41 pm -
Nonstop1h 57m
Sun 9/209:20 pm -
Nonstop1h 52m
Deal found 8/27![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/1811:21 am -
1 stop4h 29m
Fri 1/89:55 am -
1 stop6h 51m
Deal found 8/30![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/117:47 am -
Nonstop1h 52m
Tue 9/159:20 pm -
Nonstop1h 52m
Deal found 8/27![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/246:39 am -
1 stop4h 08m
Sun 10/2510:12 am -
1 stop4h 45m
Deal found 8/31![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/161:05 pm -
1 stop5h 14m
Sat 9/197:13 pm -
1 stop3h 38m
Deal found 8/30![Delta logo]()
$548
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/137:40 am -
Nonstop1h 52m
Fri 9/185:51 pm -
1 stop5h 53m
Deal found 8/29![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/31:05 pm -
1 stop4h 54m
Sun 10/47:13 pm -
1 stop3h 38m
Deal found 8/31![Delta logo]()
$594
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/245:04 pm -
1 stop5h 42m
Wed 10/281:00 pm -
1 stop7h 04m
Deal found 8/30![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/1311:00 am -
1 stop5h 39m
Mon 11/161:31 pm -
2 stops5h 35m
Deal found 8/28![Delta logo]()
$614
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/127:50 am -
Nonstop1h 52m
Fri 10/169:20 pm -
Nonstop1h 51m
Deal found 8/31![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/125:10 am -
1 stop3h 34m
Fri 10/165:31 pm -
1 stop5h 51m
Deal found 8/31![Delta logo]()
$652
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/276:31 pm -
Nonstop2h 02m
Wed 9/304:00 pm -
Nonstop1h 56m
Deal found 8/28![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/251:05 pm -
1 stop5h 14m
Sun 9/277:13 pm -
1 stop3h 38m
Deal found 8/30![Delta logo]()
$663
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/105:55 am -
1 stop5h 24m
Thu 11/129:30 pm -
Nonstop1h 59m
Deal found 9/1![United Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/2510:42 am -
1 stop6h 37m
Mon 9/287:13 pm -
1 stop4h 05m
Deal found 8/29![Delta logo]()
$689
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated September 1, 2026 and is based on user searches.
This ezTravel 易遊網 deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ezTravel 易遊網 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 8/29![Frontier logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/116:41 pm -
Nonstop2h 18m
Tue 9/1510:39 pm -
Nonstop1h 50m
Deal found 8/27![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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
Mon 9/215:00 am -
1 stop5h 47m
Deal found 8/31![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/236:07 pm -
Nonstop2h 38m
Sat 9/261:46 pm -
1 stop8h 37m
Deal found 8/30![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/256:07 pm -
Nonstop2h 38m
Mon 9/284:00 pm -
Nonstop2h 37m
Deal found 8/31![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/256:07 pm -
Nonstop2h 38m
Tue 9/294:00 pm -
Nonstop2h 37m
Deal found 8/31![American Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/308:23 am -
1 stop4h 57m
Sat 10/37:13 pm -
1 stop3h 38m
Deal found 8/30![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/136:39 am -
1 stop6h 57m
Sat 10/176:20 am -
1 stop5h 25m
Deal found 8/28![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/135:10 am -
1 stop3h 34m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 8/29![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/145:53 pm -
1 stop5h 06m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 8/31![United Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/164:41 pm -
1 stop5h 05m
Mon 10/198:47 am -
Nonstop2h 28m
Deal found 9/1![United Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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
Sun 10/256:00 am -
1 stop7h 21m
Deal found 8/31![American Airlines logo]()
$310
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 September 1, 2026.
Search for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/288:52 pm -
1 stop27h 31m
Deal found 8/31![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Deal found 8/27![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/268:39 pm -
2 stops44h 24m
Deal found 8/28![Multiple Airlines logo]()
$164
This Trip.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:55 am -
2 stops14h 28m
Deal found 8/29![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 -
3 stops59h 15m
Deal found 8/27![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/97:08 pm -
2 stops28h 13m
Deal found 8/27![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Deal found 8/28![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/52:56 pm -
1 stop13h 17m
Deal found 8/27![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/28:52 pm -
2 stops43h 41m
Deal found 8/29![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 stops34h 55m
Deal found 8/28![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/68:45 pm -
2 stops26h 36m
Deal found 8/27![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 -
2 stops28h 41m
Deal found 8/27![Multiple Airlines logo]()
$212
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 September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (Frontier) |
One-way from | $145 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $299 |
Good round-trip deal | $377 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 7,457,451 searches. Data last updated September 1, 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
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sat 10/3
6:31 pm-8:33 pm
Nonstop2h 02m
Chicago O'Hare Intl
Sun 10/4
9:20 pm-11:11 pm
Nonstop1h 51m
$279
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 11/11
5:50 pm-11:59 pm
1 stop5h 09m
Chicago O'Hare Intl
Sat 11/14
8:40 am-10:31 am
Nonstop2h 51m
$291
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Tue 10/13
6:39 am-11:40 am
1 stop4h 01m
Chicago O'Hare Intl
Sat 10/17
9:59 am-3:58 pm
1 stop6h 59m
$301
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Wed 11/11
11:28 am-4:39 pm
1 stop4h 11m
Chicago Midway
Sat 11/14
10:34 am-3:54 pm
1 stop6h 20m
$301
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Tue 10/13
5:10 am-8:44 am
1 stop3h 34m
Chicago Midway
Sat 10/17
10:12 am-4:00 pm
1 stop5h 48m
$314
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 10/16
4:41 pm-10:46 pm
1 stop5h 05m
Chicago O'Hare Intl
Mon 10/19
8:47 am-10:15 am
Nonstop2h 28m
$323
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 11/6
5:50 pm-11:59 pm
1 stop5h 09m
Chicago O'Hare Intl
Mon 11/9
8:40 am-10:31 am
Nonstop2h 51m
$359
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Sat 9/12
11:22 am-6:31 pm
1 stop6h 09m
Chicago O'Hare Intl
Wed 9/16
5:00 am-9:27 am
1 stop5h 27m
$359
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 9/11
7:47 am-9:39 am
Nonstop1h 52m
Chicago O'Hare Intl
Sun 9/13
9:20 pm-11:12 pm
Nonstop1h 52m
$369
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 12/11
6:00 am-9:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Tue 12/15
7:50 pm-9:42 pm
Nonstop2h 52m
$370
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
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 South Dakota to Chicago
USSD-CHI
FSD-ORD
RAP-ORD
FSD-MDW
RAP-MDW
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 $251). 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 September 1, 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 in the morning could potentially save you up to 21% 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 September 1, 2026.
The most flights from USSD to CHI are scheduled on a Monday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from South Dakota to Chicago?
Airfare is typical for this route at the moment.
South Dakota to Chicago flights typically cost between $249 and $358 in September.The cheapest round-trip price found within the last 5 days was $261 on Frontier (Sep 18-Sep 21).
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 evenings 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 September 1, 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 September 1, 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 7,457,451 searches. Data last updated September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$289 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$325 | FlexibilityNo cancel fee | On-time69% |