$186+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/109:45 am -
Nonstop2h 02m
Sun 12/138:40 am -
Nonstop1h 57m
Deal found 11/6![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/277:36 pm -
Nonstop2h 12m
Mon 11/3010:33 pm -
Nonstop2h 11m
Deal found 11/6![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/103:19 pm -
Nonstop2h 17m
Sun 12/135:00 am -
1 stop7h 24m
Deal found 11/5![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/193:11 pm -
Nonstop1h 54m
Sat 1/28:44 am -
Nonstop1h 55m
Deal found 11/8![United Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/257:36 pm -
Nonstop2h 12m
Sun 11/294:59 pm -
Nonstop2h 07m
Deal found 11/8![American Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/56:00 am -
Nonstop2h 34m
Sat 12/127:50 pm -
Nonstop2h 52m
Deal found 11/6![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/15:02 am -
1 stop6h 57m
Mon 12/75:30 pm -
1 stop5h 47m
Deal found 11/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:59 pm -
1 stop6h 46m
Sun 12/66:20 am -
1 stop3h 52m
Deal found 11/10![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:11 pm -
Nonstop2h 07m
Thu 11/2612:50 pm -
Nonstop1h 57m
Deal found 11/9![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/56:11 am -
1 stop8h 48m
Sat 12/124:00 pm -
1 stop6h 32m
Deal found 11/6![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:01 am -
1 stop5h 49m
Sun 12/135:30 pm -
1 stop5h 47m
Deal found 11/7![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/28:27 am -
1 stop6h 26m
Sat 12/512:32 pm -
1 stop6h 42m
Deal found 11/6![Delta logo]()
$364
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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
Nonstop2h 39m
Sat 1/97:45 pm -
Nonstop2h 53m
Deal found 11/9![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/812:59 pm -
1 stop3h 51m
Tue 12/1512:39 pm -
1 stop6h 35m
Deal found 11/8![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1512:14 pm -
Nonstop2h 17m
Fri 12/185:00 am -
1 stop6h 24m
Deal found 11/9![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 1/106:00 am -
Nonstop2h 39m
Sun 1/177:45 pm -
Nonstop2h 53m
Deal found 11/7![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:43 pm -
1 stop3h 53m
Mon 2/13:36 pm -
1 stop3h 48m
Deal found 11/9![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/912:18 pm -
1 stop6h 10m
Sun 12/137:50 pm -
Nonstop2h 52m
Deal found 11/6![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/238:31 am -
1 stop3h 19m
Mon 11/305:29 pm -
1 stop5h 31m
Deal found 11/5![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/238:31 am -
1 stop6h 24m
Sun 11/296:23 am -
1 stop3h 57m
Deal found 11/5![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/215:05 am -
1 stop3h 59m
Thu 12/36:20 am -
1 stop3h 52m
Deal found 11/5![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/226:00 am -
Nonstop1h 55m
Sat 11/287:45 pm -
Nonstop1h 52m
Deal found 11/5![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/278:31 am -
1 stop6h 24m
Tue 12/15:33 pm -
1 stop5h 44m
Deal found 11/5![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:31 am -
1 stop3h 17m
Mon 11/305:42 pm -
1 stop5h 18m
Deal found 11/5![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/233:11 pm -
Nonstop1h 54m
Wed 12/309:20 pm -
Nonstop2h 06m
Deal found 11/8![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
1 stop5h 04m
Sat 1/95:40 pm -
1 stop6h 12m
Deal found 11/9![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/2412:39 pm -
1 stop6h 50m
Sat 11/288:40 am -
Nonstop2h 51m
Deal found 11/5![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:21 am -
1 stop4h 29m
Tue 12/1510:24 am -
1 stop4h 36m
Deal found 11/10![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:30 am -
1 stop5h 34m
Mon 11/308:40 am -
Nonstop2h 51m
Deal found 11/9![United Airlines logo]()
$479
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:44 am -
1 stop5h 09m
Sun 2/75:40 pm -
1 stop6h 12m
Deal found 11/10![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:42 am -
2 stops10h 44m
Tue 12/159:59 am -
1 stop5h 01m
Deal found 11/10![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:30 pm -
Nonstop2h 33m
Wed 11/258:40 am -
Nonstop2h 51m
Deal found 11/5![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:44 am -
1 stop5h 13m
Sun 2/71:54 pm -
2 stops9h 58m
Deal found 11/10![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/66:00 am -
1 stop5h 02m
Mon 2/81:54 pm -
2 stops9h 58m
Deal found 11/9![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/610:44 am -
1 stop5h 09m
Mon 2/81:41 pm -
2 stops10h 11m
Deal found 11/9![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:05 am -
1 stop3h 59m
Thu 11/266:23 am -
1 stop5h 54m
Deal found 11/9![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/195:10 pm -
1 stop4h 29m
Sat 1/26:29 am -
1 stop3h 43m
Deal found 11/8![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/246:45 am -
1 stop4h 05m
Fri 11/275:29 pm -
1 stop4h 20m
Deal found 11/8![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
2 stops9h 27m
Sat 1/96:00 am -
1 stop5h 02m
Deal found 11/9![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/305:29 pm -
1 stop5h 31m
Deal found 11/5![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/201:00 pm -
1 stop3h 50m
Tue 3/239:55 am -
1 stop5h 55m
Deal found 11/9![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:34 am -
1 stop5h 19m
Thu 12/319:59 am -
1 stop4h 14m
Deal found 11/9![Delta logo]()
$472
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated November 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:11 pm -
Nonstop2h 07m
Thu 11/2612:50 pm -
Nonstop1h 57m
Deal found 11/9![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/257:36 pm -
Nonstop2h 12m
Sun 11/294:59 pm -
Nonstop2h 07m
Deal found 11/8![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/277:36 pm -
Nonstop2h 12m
Mon 11/3010:33 pm -
Nonstop2h 11m
Deal found 11/6![American Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/15:02 am -
1 stop6h 57m
Mon 12/75:30 pm -
1 stop5h 47m
Deal found 11/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/28:27 am -
1 stop6h 26m
Sat 12/512:32 pm -
1 stop6h 42m
Deal found 11/6![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:59 pm -
1 stop6h 46m
Sun 12/66:20 am -
1 stop3h 52m
Deal found 11/10![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/511:06 am -
1 stop4h 44m
Sat 12/125:30 pm -
1 stop6h 16m
Deal found 11/6![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/109:45 am -
Nonstop2h 02m
Sun 12/138:40 am -
Nonstop1h 57m
Deal found 11/6![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/103:19 pm -
Nonstop2h 17m
Sun 12/135:00 am -
1 stop7h 24m
Deal found 11/5![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:01 am -
1 stop5h 49m
Sun 12/135:30 pm -
1 stop5h 47m
Deal found 11/7![Delta logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:05 am -
2 stops34h 55m
Sun 12/206:08 am -
1 stop27h 41m
Deal found 11/7![Multiple Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/193:11 pm -
Nonstop1h 54m
Sat 1/28:44 am -
Nonstop1h 55m
Deal found 11/8![United Airlines 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 November 10, 2026.
Search for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:07 am -
1 stop16h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/3110:02 pm -
3 stops49h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/3110:02 pm -
3 stops48h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/185:37 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 2/156:27 pm -
2 stops29h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$206
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/307:48 am -
Nonstop1h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/206:38 pm -
1 stop28h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/309:45 pm -
1 stop31h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 -
2 stops25h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:27 am -
1 stop8h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/155:02 am -
1 stop11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/206:38 pm -
2 stops37h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$271
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $329 (United Airlines) |
One-way from | $186 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $364 |
Good round-trip deal | $410 or less |
Good one-way deal | $338 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 November 10, 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 1/31
10:02 pm-12:26 am
3 stops49h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Mon 2/15
6:27 pm-11:46 pm
2 stops29h 19m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$206
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 11/20
6:38 pm-11:34 pm
1 stop28h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$210
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Mon 12/14
11:07 am-10:00 pm
3 stops33h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$215
Rapid CityChicago
RAP Rapid City - MDW Chicago Midway
RAPMDW
Rapid City
Sun 1/31
10:02 pm-11:46 pm
2 stops48h 44m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$240
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Sun 11/22
10:08 pm-12:53 am
2 stops25h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$247
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Tue 12/15
5:02 am-4:43 pm
1 stop11h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sat 12/19
10:52 am-6:29 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 12/18
5:37 pm-10:29 pm
2 stops28h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Wed 1/6
5:11 am-7:14 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Showing 1-10 of 59 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.
RAP-ORD
FSD-MDW
FSD-ORD
RAP-MDW
ABR-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
RAP-ORD
FSD-MDW
FSD-ORD
RAP-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 $284). Flying from South Dakota to Chicago in November is currently the most expensive (average of $472). 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 November 10, 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 November 10, 2026.
The most flights from USSD to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (12 on average).
How far ahead should I book a flight from South Dakota to Chicago?
Booking 76 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 November 10, 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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$221 | Average$356 | FlexibilityNo cancel fee | On-time69% |