$150+ Cheap flights from South Dakota 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Nov 28 — Dec 51
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 October 29, 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 October 29, 2026.
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:48 am -
Nonstop1h 57m
Sun 11/228:40 am -
Nonstop1h 52m
Deal found 10/25![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/27. 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.
Sat 12/1211:06 am -
1 stop4h 37m
Tue 12/156:20 am -
1 stop5h 18m
Deal found 10/27![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/243:11 pm -
Nonstop1h 54m
Fri 12/259:20 pm -
Nonstop2h 06m
Deal found 10/25![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:36 pm -
Nonstop2h 12m
Sun 11/225:00 am -
1 stop7h 33m
Deal found 10/25![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/126:00 am -
Nonstop2h 34m
Tue 12/157:50 pm -
Nonstop2h 52m
Deal found 10/27![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 39m
Sat 11/2112:30 pm -
1 stop6h 36m
Deal found 10/25![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 41m
Sun 11/226:23 am -
1 stop5h 54m
Deal found 10/25![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/2611:29 am -
1 stop7h 10m
Sat 11/289:59 am -
1 stop6h 55m
Deal found 10/27![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 12/1412:59 pm -
1 stop6h 46m
Fri 12/188:40 pm -
1 stop15h 18m
Deal found 10/27![Delta logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/199:56 pm -
1 stop30h 14m
Mon 11/2312:05 pm -
2 stops22h 07m
Deal found 10/24![Multiple Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/106:00 am -
Nonstop1h 55m
Sat 11/148:40 am -
Nonstop1h 52m
Deal found 10/26![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/198:31 am -
1 stop3h 19m
Sun 11/2212:30 pm -
1 stop6h 36m
Deal found 10/28![Delta logo]()
$354
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 October 29, 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 October 29, 2026.
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:48 am -
Nonstop1h 57m
Sat 11/219:30 pm -
Nonstop1h 59m
Deal found 10/25![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 41m
Sun 11/226:23 am -
1 stop5h 54m
Deal found 10/25![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/243:11 pm -
Nonstop1h 54m
Fri 12/259:20 pm -
Nonstop2h 06m
Deal found 10/25![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/198:31 am -
1 stop3h 19m
Sun 11/2212:30 pm -
1 stop6h 36m
Deal found 10/29![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/194:36 pm -
1 stop3h 57m
Sun 11/226:23 am -
1 stop5h 00m
Deal found 10/29![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/127:48 am -
Nonstop1h 57m
Sun 11/159:30 pm -
Nonstop1h 59m
Deal found 10/29![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 10/27. 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 4/2311:30 am -
1 stop7h 04m
Mon 4/265:20 pm -
1 stop6h 19m
Deal found 10/27![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/115:00 am -
1 stop5h 19m
Wed 11/188:40 am -
1 stop5h 08m
Deal found 10/28![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:48 am -
2 stops6h 03m
Sat 11/141:31 pm -
2 stops6h 02m
Deal found 10/26![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:40 pm -
Nonstop1h 55m
Sun 11/228:40 am -
Nonstop1h 52m
Deal found 10/28![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 11/1111:28 am -
1 stop4h 11m
Sun 11/155:29 pm -
1 stop6h 12m
Deal found 10/29![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/117:40 am -
Nonstop1h 58m
Sun 12/138:40 am -
Nonstop1h 57m
Deal found 10/27![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:28 am -
1 stop4h 11m
Sat 11/1410:34 am -
1 stop6h 20m
Deal found 10/26![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/191:30 pm -
Nonstop2h 33m
Sun 11/228:40 am -
Nonstop2h 51m
Deal found 10/29![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 11/116:45 am -
1 stop4h 05m
Wed 11/1810:34 am -
1 stop6h 20m
Deal found 10/29![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 11/277:48 am -
Nonstop1h 57m
Sun 11/297:45 pm -
Nonstop1h 52m
Deal found 10/29![United Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 10/27. 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 12/115:02 am -
1 stop3h 53m
Mon 12/1410:24 am -
1 stop5h 56m
Deal found 10/27![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 11/256:40 pm -
Nonstop1h 55m
Sun 11/297:45 pm -
Nonstop1h 52m
Deal found 10/27![United Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 10/27. 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.
Wed 12/168:27 am -
1 stop3h 32m
Mon 12/2111:47 am -
1 stop11h 09m
Deal found 10/27![Delta logo]()
$442
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/67:48 am -
Nonstop1h 57m
Sun 11/87:00 am -
1 stop5h 35m
Deal found 10/27![United Airlines logo]()
$459
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 39m
Sun 11/2212:30 pm -
1 stop6h 36m
Deal found 10/26![Delta logo]()
$459
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/267:00 am -
1 stop5h 15m
Sun 11/298:40 am -
Nonstop2h 51m
Deal found 10/25![United Airlines logo]()
$464
This KAYAK deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:59 pm -
1 stop6h 46m
Fri 12/188:40 pm -
1 stop26h 16m
Deal found 10/26![Delta logo]()
$462
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/45:55 am -
1 stop5h 24m
Sun 11/87:00 am -
1 stop5h 35m
Deal found 10/28![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 12/213:36 pm -
1 stop6h 03m
Thu 12/319:59 am -
1 stop4h 14m
Deal found 10/27![Delta logo]()
$462
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/268:30 am -
1 stop5h 25m
Sat 11/288:40 am -
Nonstop2h 51m
Deal found 10/25![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/196:35 am -
1 stop9h 49m
Mon 12/2811:47 am -
1 stop12h 05m
Deal found 10/28![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 10/27. 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.
Sun 12/138:27 am -
1 stop3h 32m
Mon 12/219:29 am -
2 stops13h 27m
Deal found 10/27![Delta logo]()
$481
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/251:30 pm -
Nonstop2h 33m
Sat 11/288:40 am -
Nonstop2h 51m
Deal found 10/28![United Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 12/158:27 am -
1 stop8h 23m
Thu 12/1710:24 am -
1 stop12h 53m
Deal found 10/27![Delta logo]()
$483
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated October 29, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated October 29, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/106:00 am -
Nonstop1h 55m
Sat 11/148:40 am -
Nonstop1h 52m
Deal found 10/26![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/127:18 pm -
Nonstop2h 12m
Mon 11/163:00 pm -
1 stop5h 54m
Deal found 10/28![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/27. 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 11/1311:00 am -
1 stop5h 41m
Tue 11/1712:38 pm -
1 stop6h 28m
Deal found 10/27![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/198:31 am -
1 stop3h 19m
Sun 11/2212:30 pm -
1 stop6h 36m
Deal found 10/28![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/194:36 pm -
1 stop3h 57m
Sun 11/226:23 am -
1 stop5h 00m
Deal found 10/28![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:48 am -
Nonstop1h 57m
Sun 11/228:40 am -
Nonstop1h 52m
Deal found 10/25![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/207:36 pm -
Nonstop2h 12m
Sun 11/225:00 am -
1 stop7h 33m
Deal found 10/25![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 39m
Sat 11/2112:30 pm -
1 stop6h 36m
Deal found 10/25![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/201:00 pm -
1 stop3h 41m
Sun 11/226:23 am -
1 stop5h 54m
Deal found 10/25![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/255:50 pm -
1 stop5h 09m
Wed 12/27:50 pm -
Nonstop2h 52m
Deal found 10/28![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:40 pm -
Nonstop1h 55m
Sun 11/297:45 pm -
Nonstop1h 52m
Deal found 10/24![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/2611:29 am -
1 stop7h 10m
Sat 11/289:59 am -
1 stop6h 55m
Deal found 10/27![Delta logo]()
$340
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 October 29, 2026.
Search for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated October 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2210:08 pm -
1 stop30h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$150
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 12/205:00 am -
Nonstop2h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$160
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/221:30 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/44:17 pm -
2 stops32h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/910:44 am -
1 stop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$230
This American Airlines deal was found by Cheapflights users on 10/27. 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 1/16:00 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/1510:44 am -
1 stop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/410:45 am -
2 stops24h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/2210:44 am -
2 stops12h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/411:12 am -
Nonstop1h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/28:39 pm -
2 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 10/27. 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 1/11:32 pm -
Nonstop2h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![United Airlines logo]()
$289
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 October 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (United Airlines) |
One-way from | $150 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $379 |
Good round-trip deal | $433 or less |
Good one-way deal | $320 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 October 29, 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
Sun 11/22
10:08 pm-11:00 am
2 stops35h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$156
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Sun 11/22
1:30 pm-5:03 pm
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Sat 1/9
10:44 am-4:53 pm
1 stop5h 09m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$230
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Sat 1/23
10:44 am-11:55 pm
2 stops12h 11m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$235
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 1/1
6:00 am-2:12 pm
1 stop7h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Fri 12/4
10:45 am-11:33 am
2 stops24h 48m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$265
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Fri 1/15
10:44 am-4:53 pm
1 stop5h 09m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Fri 1/22
10:44 am-11:55 pm
2 stops12h 11m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$270
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 12/4
11:12 am-1:10 pm
Nonstop1h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 12/4
7:34 pm-9:50 pm
Nonstop2h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
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
FSD-MDW
RAP-ORD
ATY-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
FSD-MDW
RAP-ORD
ATY-MDW
What is the cheapest month to book a flight from South Dakota to Chicago?
Currently, January is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $258). Flying from South Dakota to Chicago in October is currently the most expensive (average of $412). 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 October 29, 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 evening could potentially save you up to 20% on airfare.
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 $279 and $383 in November.The cheapest round-trip price found within the last 5 days was $319 on United Airlines (Nov 20-Nov 22).
How far ahead should I book a flight from South Dakota to Chicago?
Booking 78 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
Merrillville
Lansing
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.
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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 October 29, 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 October 29, 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 October 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$341 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$221 | Average$356 | FlexibilityNo cancel fee | On-time69% |