$101+ Cheap flights from South Dakota to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Sep 4 — Sep 111
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from South Dakota to Chicago
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Cheapest flights from South Dakota to ChicagoExplore the most affordable flight options available from South Dakota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
Explore the most affordable flight options available from South Dakota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
This CheapOair deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:52 pm -
1 stop27h 31m
Sat 10/1011:06 am -
1 stop7h 30m
Deal found 8/4![Frontier logo]()
$190
This CheapOair deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:52 pm -
1 stop27h 31m
Mon 9/216:30 am -
1 stop13h 37m
Deal found 7/31![Frontier logo]()
$200
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:24 am -
Nonstop2h 06m
Tue 9/810:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/266:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/46:06 pm -
1 stop6h 12m
Mon 9/710:40 pm -
Nonstop1h 50m
Deal found 8/5![American Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:23 pm -
Nonstop2h 11m
Sat 9/59:40 am -
1 stop7h 56m
Deal found 8/4![American Airlines logo]()
$258
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:39 pm -
Nonstop1h 59m
Sun 8/309:30 pm -
Nonstop1h 52m
Deal found 8/2![United Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:37 pm -
Nonstop2h 24m
Wed 10/288:40 am -
Nonstop2h 51m
Deal found 8/1![United Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:07 pm -
Nonstop2h 38m
Sun 9/279:40 am -
Nonstop2h 35m
Deal found 8/1![American Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:31 pm -
Nonstop2h 24m
Wed 9/95:00 am -
1 stop5h 27m
Deal found 8/3![United Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:31 pm -
Nonstop2h 24m
Sun 9/68:58 am -
Nonstop2h 28m
Deal found 8/3![United Airlines logo]()
$279
Best flights from South Dakota to ChicagoDiscover carefully curated flight deals from South Dakota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
Discover carefully curated flight deals from South Dakota to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/247:48 am -
Nonstop1h 57m
Sat 11/287:45 pm -
Nonstop1h 52m
Deal found 8/2![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/108:28 am -
1 stop3h 22m
Sat 11/1412:30 pm -
1 stop6h 40m
Deal found 8/4![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:56 pm -
1 stop6h 18m
Thu 10/14:00 pm -
Nonstop2h 37m
Deal found 7/31![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/46:39 pm -
Nonstop1h 59m
Mon 9/79:30 pm -
Nonstop1h 52m
Deal found 8/5![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:05 pm -
1 stop5h 14m
Sat 9/197:13 pm -
1 stop3h 38m
Deal found 8/3![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:31 pm -
Nonstop2h 24m
Wed 9/95:00 am -
1 stop5h 27m
Deal found 8/1![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:26 pm -
1 stop6h 04m
Sun 8/306:00 am -
1 stop4h 20m
Deal found 7/31![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:26 pm -
1 stop6h 04m
Sun 8/306:00 am -
1 stop4h 20m
Deal found 8/2![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/135:50 pm -
1 stop5h 09m
Sun 11/158:40 am -
Nonstop2h 51m
Deal found 8/2![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/132:23 pm -
1 stop4h 16m
Sun 11/156:30 am -
1 stop5h 19m
Deal found 8/2![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:48 pm -
1 stop5h 11m
Sun 9/135:00 am -
1 stop5h 27m
Deal found 8/4![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/1311:29 am -
1 stop4h 10m
Sun 11/1512:30 pm -
1 stop4h 25m
Deal found 8/2![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/125:50 pm -
1 stop5h 09m
Sun 11/158:40 am -
Nonstop2h 51m
Deal found 8/2![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:46 am -
1 stop6h 15m
Wed 9/99:59 am -
1 stop6h 52m
Deal found 8/4![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:31 pm -
Nonstop2h 24m
Fri 8/217:59 pm -
2 stops17h 25m
Deal found 7/31![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:05 pm -
1 stop4h 54m
Mon 9/217:13 pm -
1 stop3h 38m
Deal found 7/31![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:37 pm -
Nonstop2h 24m
Sat 10/178:47 am -
Nonstop2h 28m
Deal found 8/1![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:56 pm -
1 stop4h 37m
Wed 9/308:25 am -
1 stop5h 41m
Deal found 8/2![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/248:28 am -
1 stop3h 22m
Sat 11/2812:30 pm -
1 stop6h 40m
Deal found 8/2![Delta logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:33 pm -
2 stops21h 27m
Tue 9/83:56 pm -
1 stop7h 48m
Deal found 8/2![United Airlines logo]()
$508
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 10/206:39 am -
1 stop4h 08m
Wed 10/2112:27 pm -
1 stop4h 31m
Deal found 8/5![Delta logo]()
$465
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am -
1 stop5h 28m
Thu 8/275:00 am -
1 stop5h 43m
Deal found 7/31![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 8/5. 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 12/58:28 am -
2 stops9h 36m
Sun 12/612:30 pm -
1 stop6h 40m
Deal found 8/5![Delta logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:47 am -
Nonstop1h 52m
Wed 9/98:45 am -
Nonstop1h 52m
Deal found 8/4![United Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:00 am -
2 stops14h 00m
Sun 9/205:00 am -
1 stop5h 44m
Deal found 7/31![United Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 11/1211:29 am -
1 stop4h 10m
Sun 11/1510:22 am -
1 stop6h 33m
Deal found 8/5![Delta logo]()
$518
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:54 am -
2 stops6h 05m
Tue 9/87:13 pm -
1 stop3h 38m
Deal found 8/3![Delta logo]()
$518
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/214:28 pm -
1 stop5h 19m
Mon 8/246:59 am -
2 stops8h 49m
Deal found 8/2![Delta logo]()
$524
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:54 am -
1 stop5h 03m
Mon 9/77:25 pm -
1 stop3h 37m
Deal found 8/1![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:15 am -
2 stops7h 35m
Tue 9/86:24 pm -
1 stop4h 27m
Deal found 8/1![Delta logo]()
$597
Last-minute flights from South Dakota to ChicagoDiscover last-minute flight deals from South Dakota to Chicago. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from South Dakota to Chicago. Data last updated August 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/266:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:39 pm -
Nonstop1h 59m
Sun 8/309:30 pm -
Nonstop1h 52m
Deal found 8/2![United Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/276:24 am -
Nonstop2h 06m
Sun 8/303:00 pm -
Nonstop1h 53m
Deal found 8/2![American Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:31 pm -
Nonstop2h 24m
Wed 9/95:00 am -
1 stop5h 27m
Deal found 8/3![United Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:23 pm -
Nonstop2h 11m
Sat 9/59:40 am -
1 stop7h 56m
Deal found 8/4![American Airlines logo]()
$258
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/46:06 pm -
1 stop6h 12m
Mon 9/710:40 pm -
Nonstop1h 50m
Deal found 8/5![American Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:31 pm -
Nonstop2h 24m
Sun 9/68:58 am -
Nonstop2h 28m
Deal found 8/3![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:24 am -
Nonstop2h 06m
Tue 9/810:40 pm -
Nonstop1h 50m
Deal found 8/4![American Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:52 pm -
1 stop27h 31m
Mon 9/216:30 am -
1 stop13h 37m
Deal found 7/31![Frontier logo]()
$200
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:07 pm -
Nonstop2h 38m
Sun 9/279:40 am -
Nonstop2h 35m
Deal found 8/1![American Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:05 am -
1 stop3h 43m
Wed 10/75:31 pm -
1 stop5h 51m
Deal found 8/3![Delta logo]()
$279
One-way flights from South Dakota to ChicagoSearch for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
Search for one-way flight options from South Dakota to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:56 pm -
1 stop16h 40m
Deal found 8/3![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:56 pm -
1 stop16h 40m
Deal found 8/4![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:48 pm -
1 stop13h 13m
Deal found 8/1![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:52 pm -
1 stop27h 31m
Deal found 8/1![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:52 pm -
1 stop27h 31m
Deal found 8/1![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 10/58:52 pm -
1 stop27h 31m
Deal found 8/4![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:56 pm -
1 stop16h 40m
Deal found 7/31![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:48 pm -
1 stop13h 13m
Deal found 8/2![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/203:34 pm -
3 stops32h 11m
Deal found 7/31![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/511:29 am -
2 stops30h 17m
Deal found 8/3![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:30 pm -
1 stop26h 32m
Deal found 8/1![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/3010:00 pm -
2 stops36h 55m
Deal found 8/2![Multiple Airlines logo]()
$186
Find flight deals from South Dakota to Chicago
Keep the following information in mind while searching for South Dakota to Chicago flight deals. Data was last updated August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (CheapOair) |
One-way from | $101 (CheapOair) |
Popular in | July |
Cheapest in | January |
Average price | $249 |
Good round-trip deal | $343 or less |
Good one-way deal | $308 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from South Dakota to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 5, 2026.
Use the filters below to find and compare flights from South Dakota to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Tue 11/24
7:48 am-9:45 am
Nonstop1h 57m
Chicago O'Hare Intl
Sat 11/28
7:45 pm-9:37 pm
Nonstop1h 52m
$259
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 9/4
6:39 pm-8:38 pm
Nonstop1h 59m
Chicago O'Hare Intl
Mon 9/7
9:30 pm-11:22 pm
Nonstop1h 52m
$266
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Wed 9/2
1:31 pm-4:55 pm
Nonstop2h 24m
Chicago O'Hare Intl
Wed 9/9
5:00 am-9:27 am
1 stop5h 27m
$271
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Tue 11/10
8:28 am-11:50 am
1 stop3h 22m
Chicago Midway
Sat 11/14
12:30 pm-7:10 pm
1 stop6h 40m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Fri 9/11
1:05 pm-6:19 pm
1 stop5h 14m
Chicago Midway
Sat 9/19
7:13 pm-10:51 pm
1 stop3h 38m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 8/28
1:26 pm-7:30 pm
1 stop6h 04m
Chicago O'Hare Intl
Sun 8/30
6:00 am-10:20 am
1 stop4h 20m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Thu 8/27
1:26 pm-7:30 pm
1 stop6h 04m
Chicago O'Hare Intl
Sun 8/30
6:00 am-10:20 am
1 stop4h 20m
$279
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 11/13
2:23 pm-7:39 pm
1 stop4h 16m
Chicago O'Hare Intl
Sun 11/15
6:30 am-10:49 am
1 stop5h 19m
$299
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Thu 9/24
4:56 pm-12:14 am
1 stop6h 18m
Chicago O'Hare Intl
Thu 10/1
4:00 pm-5:37 pm
Nonstop2h 37m
$309
Rapid CityChicago
RAP Rapid City - ORD Chicago O'Hare Intl
RAPORD
Rapid City
Fri 11/13
5:50 pm-11:59 pm
1 stop5h 09m
Chicago O'Hare Intl
Sun 11/15
8:40 am-10:31 am
Nonstop2h 51m
$309
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from South Dakota to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from South Dakota with our price prediction graph.
FSD-ORD
RAP-ORD
FSD-MDW
RAP-MDW
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
FSD-ORD
RAP-ORD
FSD-MDW
RAP-MDW
What is the cheapest month to book a flight from South Dakota to Chicago?
Currently, November is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $243). Flying from South Dakota to Chicago in September is currently the most expensive (average of $359). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SD to CHI?
Find hourly flight availability from South Dakota to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 5, 2026.
One of the essential ways to save on airfare from South Dakota to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 28% on airfare.
Weekly flight availability from South Dakota to Chicago
Explore weekly flight availability from South Dakota to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 5, 2026.
The most flights from USSD to CHI are scheduled on a Tuesday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from South Dakota to Chicago?
Airfare is below average for this route at the moment.
South Dakota to Chicago flights typically cost between $249 and $364 in October.The cheapest round-trip price found within the last 5 days was $190 on Frontier (Oct 2-Oct 10).
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. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from South Dakota to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for South Dakota to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from South Dakota to Chicago by cabin class
Find flights from South Dakota to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
South Dakota and Chicago flights
Browse other South Dakota and Chicago flight options. Last updated on August 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
South Dakota to Chicago flights
Consider these flights traveling from South Dakota to Chicago.
Top 2 airlines flying from South Dakota to Chicago
Discover the top 2 airlines that operate flights from South Dakota to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$278 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$328 | FlexibilityNo cancel fee | On-time69% |