$155+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Oct 27 — Nov 31
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 27, 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 27, 2026.
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Fri 12/117:40 am -
Nonstop1h 58m
Sun 12/138:20 pm -
Nonstop1h 52m
Deal found 9/24![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 11/23:29 pm -
Nonstop2h 06m
Sat 11/74:47 pm -
Nonstop2h 01m
Deal found 9/27![American Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 9/24. 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 12/26:00 am -
Nonstop2h 34m
Sat 12/57:50 pm -
Nonstop2h 52m
Deal found 9/24![United Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:54 pm -
1 stop6h 05m
Sat 10/245:07 pm -
Nonstop1h 58m
Deal found 9/22![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 12/36:00 am -
Nonstop2h 34m
Sat 12/57:50 pm -
Nonstop2h 52m
Deal found 9/24![United Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:39 pm -
Nonstop2h 01m
Sat 10/1710:48 pm -
Nonstop1h 53m
Deal found 9/24![American Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/161:37 pm -
Nonstop2h 24m
Sun 10/188:47 am -
Nonstop2h 24m
Deal found 9/25![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/1211:01 am -
1 stop5h 49m
Wed 12/1612:39 pm -
1 stop3h 41m
Deal found 9/23![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:54 pm -
1 stop6h 05m
Wed 10/2812:11 pm -
1 stop7h 40m
Deal found 9/23![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 12/36:00 am -
Nonstop2h 34m
Sat 12/124:20 pm -
1 stop5h 48m
Deal found 9/24![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 12/22:40 pm -
1 stop5h 55m
Sat 12/512:32 pm -
1 stop4h 21m
Deal found 9/24![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 9/24. 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 11/146:48 am -
1 stop5h 00m
Mon 11/163:47 pm -
1 stop3h 46m
Deal found 9/24![Delta logo]()
$324
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 27, 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 27, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/216:31 pm -
Nonstop2h 02m
Sat 10/249:20 pm -
Nonstop1h 51m
Deal found 9/22![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 9/24. 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 12/1212:59 pm -
1 stop3h 51m
Mon 12/1412:39 pm -
1 stop6h 35m
Deal found 9/24![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 11/21:08 pm -
1 stop6h 52m
Sat 11/710:00 am -
1 stop7h 27m
Deal found 9/27![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 12/36:00 am -
Nonstop2h 34m
Sat 12/57:50 pm -
Nonstop2h 52m
Deal found 9/24![United Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/24. 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 11/146:48 am -
1 stop5h 00m
Mon 11/163:47 pm -
1 stop3h 46m
Deal found 9/24![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 9/24. 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 11/146:48 am -
1 stop5h 02m
Mon 11/161:31 pm -
2 stops6h 02m
Deal found 9/24![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Thu 10/156:31 pm -
Nonstop2h 02m
Sun 10/189:20 pm -
Nonstop1h 51m
Deal found 9/26![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/26. 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.
Thu 11/2611:00 am -
1 stop3h 55m
Mon 11/3012:38 pm -
1 stop6h 28m
Deal found 9/26![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Fri 10/166:31 pm -
Nonstop2h 02m
Sun 10/185:00 am -
1 stop5h 50m
Deal found 9/24![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 9/26. 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.
Thu 11/192:23 pm -
1 stop4h 16m
Sun 11/226:23 am -
1 stop5h 00m
Deal found 9/26![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 9/24. 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 11/141:00 pm -
1 stop3h 39m
Mon 11/1612:30 pm -
1 stop6h 36m
Deal found 9/24![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/25. 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.
Tue 10/201:37 pm -
Nonstop2h 24m
Sat 10/248:47 am -
Nonstop2h 28m
Deal found 9/25![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 9/25. 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.
Tue 10/208:30 am -
1 stop3h 17m
Tue 10/275:31 pm -
1 stop5h 51m
Deal found 9/25![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:37 pm -
Nonstop2h 24m
Mon 11/25:48 pm -
1 stop5h 42m
Deal found 9/23![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/25. 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.
Sat 10/106:45 am -
2 stops6h 14m
Tue 10/133:30 pm -
1 stop3h 58m
Deal found 9/25![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/151:37 pm -
Nonstop2h 24m
Mon 10/198:47 am -
Nonstop2h 28m
Deal found 9/25![United Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 9/25. 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.
Tue 10/134:41 pm -
1 stop5h 05m
Sat 10/178:47 am -
Nonstop2h 28m
Deal found 9/25![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:45 am -
1 stop4h 05m
Mon 11/165:29 pm -
1 stop6h 12m
Deal found 9/23![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 9/26. 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.
Wed 11/251:00 pm -
1 stop3h 39m
Mon 11/3012:30 pm -
1 stop6h 36m
Deal found 9/26![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/247:50 am -
Nonstop1h 52m
Wed 10/285:48 pm -
1 stop5h 56m
Deal found 9/26![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:30 pm -
Nonstop2h 33m
Sat 10/318:40 am -
Nonstop2h 51m
Deal found 9/22![United Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 12/168:27 am -
1 stop3h 32m
Tue 12/226:30 pm -
1 stop4h 27m
Deal found 9/24![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/215:10 am -
1 stop3h 34m
Sat 10/245:31 pm -
1 stop5h 32m
Deal found 9/22![Delta logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/211:40 am -
1 stop8h 42m
Sun 10/45:00 am -
1 stop6h 05m
Deal found 9/22![United Airlines logo]()
$565
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:00 am -
1 stop5h 39m
Sun 11/1510:34 am -
1 stop5h 24m
Deal found 9/23![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 9/26. 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.
Wed 11/258:31 am -
1 stop3h 17m
Mon 11/3012:38 pm -
1 stop6h 28m
Deal found 9/26![Delta logo]()
$489
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 10/2211:40 am -
1 stop10h 12m
Sat 10/2410:55 am -
1 stop23h 40m
Deal found 9/24![United Airlines logo]()
$602
This Delta deal was found by Cheapflights users on 9/26. 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.
Sat 12/125:02 pm -
1 stop4h 33m
Wed 12/167:05 am -
2 stops9h 15m
Deal found 9/26![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/1311:00 am -
1 stop5h 47m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/22![Delta logo]()
$499
This Delta deal was found by Cheapflights users on 9/24. 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.
Thu 10/226:45 am -
1 stop5h 02m
Sat 10/249:29 am -
2 stops9h 59m
Deal found 9/24![Delta logo]()
$523
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated September 27, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:05 am -
Nonstop1h 57m
Sat 10/106:00 am -
1 stop6h 13m
Deal found 9/23![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/78:30 am -
1 stop3h 10m
Sat 10/106:20 am -
1 stop5h 49m
Deal found 9/23![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Fri 10/97:50 am -
Nonstop1h 52m
Tue 10/139:20 pm -
Nonstop1h 51m
Deal found 9/24![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/97:39 pm -
Nonstop2h 01m
Sun 10/119:40 am -
Nonstop1h 54m
Deal found 9/27![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:39 pm -
Nonstop2h 01m
Sat 10/1710:48 pm -
Nonstop1h 53m
Deal found 9/24![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 9/25. 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.
Tue 10/208:30 am -
1 stop3h 17m
Tue 10/275:31 pm -
1 stop5h 51m
Deal found 9/25![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/216:31 pm -
Nonstop2h 02m
Sat 10/249:20 pm -
Nonstop1h 51m
Deal found 9/22![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:54 pm -
1 stop6h 05m
Sat 10/245:07 pm -
Nonstop1h 58m
Deal found 9/22![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:54 pm -
1 stop6h 05m
Wed 10/2812:11 pm -
1 stop7h 40m
Deal found 9/23![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/25. 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.
Wed 10/218:30 am -
1 stop24h 14m
Tue 10/275:31 pm -
1 stop5h 51m
Deal found 9/25![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 9/25. 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.
Wed 10/218:30 am -
1 stop24h 23m
Tue 10/276:20 am -
1 stop3h 40m
Deal found 9/25![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 9/24. 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 10/3111:29 am -
1 stop4h 18m
Mon 11/25:31 pm -
1 stop5h 59m
Deal found 9/24![Delta logo]()
$330
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 27, 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 27, 2026.
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:52 pm -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$155
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Wed 10/285:04 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Sun 10/2512:29 pm -
2 stops29h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Mon 11/236:38 pm -
1 stop18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 9/23![Multiple Airlines logo]()
$190
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Thu 10/296:00 am -
Nonstop1h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![United Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/198:44 pm -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:39 pm -
2 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:54 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![American Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 12/2410:17 pm -
2 stops30h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Wed 12/2310:06 am -
2 stops25h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$206
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 10/285:50 pm -
1 stop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![United Airlines logo]()
$211
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (United Airlines) |
One-way from | $155 (Mytrip) |
Popular in | July |
Cheapest in | January |
Average price | $321 |
Good round-trip deal | $398 or less |
Good one-way deal | $328 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 27, 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
Quickest round-trip
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 10/30
6:40 pm-8:35 pm
Nonstop1h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$194
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 10/28
5:50 pm-11:59 pm
1 stop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$211
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Fri 10/30
12:06 pm-5:47 pm
2 stops29h 41m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$236
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 10/23
11:00 am-8:53 am
1 stop21h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$237
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Wed 10/28
11:29 am-4:47 pm
1 stop4h 18m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$263
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sun 12/20
5:10 pm-2:49 pm
1 stop21h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Thu 10/29
5:45 pm-5:47 pm
2 stops24h 02m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$265
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Fri 10/23
12:06 pm-2:35 pm
2 stops26h 29m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Thu 11/5
7:48 am-9:45 am
Nonstop1h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sun 10/25
7:48 am-9:45 am
Nonstop1h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
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-MDW
FSD-MDW
RAP-ORD
ATY-ORD
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-MDW
FSD-MDW
RAP-ORD
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 September is currently the most expensive (average of $395). 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 27, 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 27, 2026.
The most flights from USSD to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (17 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 $251 and $438 in December.The cheapest round-trip price found within the last 5 days was $299 on United Airlines (Dec 11-Dec 13).
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
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 September 27, 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 27, 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$326 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$345 | FlexibilityNo cancel fee | On-time69% |