$131+ Cheap flights from Sioux Falls (FSD) 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 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Sioux Falls 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Sioux Falls Joe Foss Field to Chicago are usually found in January or August, booked 29 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Sioux Falls to Chicago
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Cheapest flights from Sioux Falls to ChicagoExplore the most affordable flight options available from Sioux Falls to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
Explore the most affordable flight options available from Sioux Falls to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Fri 10/97:39 pm -
Nonstop2h 01m
Mon 10/1210:48 pm -
Nonstop1h 53m
Deal found 9/4![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 10/247:39 pm -
Nonstop2h 01m
Sat 10/319:45 am -
Nonstop1h 54m
Deal found 9/9![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/1412:53 pm -
1 stop7h 45m
Sat 10/1710:48 pm -
Nonstop1h 53m
Deal found 9/5![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/5. 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 9/256:41 pm -
Nonstop2h 18m
Sun 9/2710:39 pm -
Nonstop1h 50m
Deal found 9/5![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/235:54 pm -
1 stop6h 05m
Fri 10/305:00 am -
1 stop7h 13m
Deal found 9/8![American Airlines logo]()
$298
This CheapOair deal was found by Cheapflights users on 9/7. 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 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
Mon 10/56:30 am -
1 stop13h 37m
Deal found 9/7![Frontier logo]()
$300
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 9/196:41 pm -
Nonstop2h 18m
Mon 9/2110:39 pm -
Nonstop1h 50m
Deal found 9/5![American Airlines logo]()
$309
This CheapOair deal was found by Cheapflights users on 9/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:52 pm -
1 stop27h 31m
Mon 9/146:30 am -
1 stop13h 37m
Deal found 9/6![Frontier logo]()
$315
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 12/411:01 am -
1 stop5h 49m
Mon 12/712:39 pm -
1 stop6h 36m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/6. 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 10/135:10 am -
1 stop3h 34m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 10/1611:00 am -
1 stop5h 47m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/5. 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 12/511:01 am -
1 stop5h 49m
Wed 12/912:39 pm -
1 stop3h 41m
Deal found 9/5![Delta logo]()
$384
Best flights from Sioux Falls to ChicagoDiscover carefully curated flight deals from Sioux Falls to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from Sioux Falls to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/4. 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 9/245:55 pm -
1 stop6h 19m
Thu 10/13:00 pm -
1 stop6h 48m
Deal found 9/4![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 9/5. 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 1/55:15 am -
1 stop3h 34m
Fri 1/155:35 pm -
1 stop5h 16m
Deal found 9/5![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/146:31 pm -
Nonstop2h 02m
Mon 10/199:20 pm -
Nonstop1h 51m
Deal found 9/6![United Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 9/2410:02 pm -
2 stops23h 37m
Thu 10/18:55 pm -
1 stop14h 05m
Deal found 9/4![Multiple Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 9/5. 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 12/511:01 am -
1 stop5h 49m
Wed 12/912:39 pm -
1 stop3h 41m
Deal found 9/5![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/247:50 am -
Nonstop1h 52m
Wed 10/285:48 pm -
1 stop5h 56m
Deal found 9/6![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 10/1611:00 am -
1 stop5h 47m
Tue 10/2010:12 am -
1 stop9h 20m
Deal found 9/6![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 9/9. 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 10/88:30 am -
1 stop6h 06m
Sun 10/116:20 am -
1 stop5h 49m
Deal found 9/9![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 9/6. 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 10/175:00 pm -
1 stop4h 27m
Sun 10/186:20 am -
1 stop3h 40m
Deal found 9/6![Delta logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 11/269:32 am -
2 stops23h 58m
Sat 11/287:45 pm -
Nonstop1h 52m
Deal found 9/4![United Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 10/187:50 am -
Nonstop1h 52m
Sun 10/189:20 pm -
Nonstop1h 51m
Deal found 9/6![United Airlines logo]()
$577
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 12/48:27 am -
2 stops9h 34m
Mon 12/712:39 pm -
1 stop6h 36m
Deal found 9/7![Delta logo]()
$504
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 10/195:04 pm -
1 stop5h 42m
Thu 10/229:20 pm -
Nonstop1h 51m
Deal found 9/6![United Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 12/48:27 am -
2 stops9h 59m
Mon 12/76:20 am -
1 stop3h 57m
Deal found 9/7![Delta logo]()
$504
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Tue 9/227:47 am -
Nonstop1h 52m
Fri 9/259:30 pm -
2 stops18h 53m
Deal found 9/8![United Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 9/7. 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 10/15:05 am -
1 stop3h 43m
Mon 10/57:13 pm -
1 stop3h 38m
Deal found 9/7![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 9/6. 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 10/171:00 pm -
1 stop3h 47m
Tue 10/201:27 pm -
2 stops6h 05m
Deal found 9/6![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 9/8. 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.
Wed 10/145:10 am -
1 stop3h 43m
Sat 10/177:00 am -
2 stops9h 00m
Deal found 9/8![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 9/5. 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 10/1611:00 am -
1 stop5h 47m
Sat 10/179:29 am -
2 stops6h 31m
Deal found 9/5![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/75:10 am -
1 stop6h 37m
Thu 10/812:27 pm -
1 stop3h 33m
Deal found 9/9![Delta logo]()
$652
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/238:30 am -
2 stops9h 30m
Fri 10/3012:27 pm -
1 stop3h 33m
Deal found 9/8![Delta logo]()
$654
This Delta deal was found by Cheapflights users on 9/5. 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 10/185:10 am -
1 stop3h 34m
Mon 10/195:31 pm -
1 stop5h 51m
Deal found 9/5![Delta logo]()
$733
Last-minute flights from Sioux Falls to ChicagoDiscover last-minute flight deals from Sioux Falls to Chicago. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Sioux Falls to Chicago. Data last updated September 9, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:52 pm -
1 stop27h 31m
Mon 9/146:30 am -
1 stop13h 37m
Deal found 9/6![Frontier logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 9/196:41 pm -
Nonstop2h 18m
Mon 9/2110:39 pm -
Nonstop1h 50m
Deal found 9/5![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/5. 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 9/256:41 pm -
Nonstop2h 18m
Sun 9/2710:39 pm -
Nonstop1h 50m
Deal found 9/5![American Airlines logo]()
$294
This CheapOair deal was found by Cheapflights users on 9/7. 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 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
Mon 10/56:30 am -
1 stop13h 37m
Deal found 9/7![Frontier logo]()
$300
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Fri 10/97:39 pm -
Nonstop2h 01m
Mon 10/1210:48 pm -
Nonstop1h 53m
Deal found 9/4![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/6. 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 10/135:10 am -
1 stop3h 34m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/6. 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 10/135:10 am -
1 stop3h 34m
Wed 10/2110:12 am -
1 stop13h 10m
Deal found 9/6![Delta logo]()
$393
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/1412:53 pm -
1 stop7h 45m
Sat 10/1710:48 pm -
Nonstop1h 53m
Deal found 9/5![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 10/1611:00 am -
1 stop5h 47m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6![Delta logo]()
$349
This deal was found by Cheapflights users on 9/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:00 pm -
1 stop3h 47m
Mon 10/195:31 pm -
1 stop5h 51m
Deal found 9/7![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/235:54 pm -
1 stop6h 05m
Fri 10/305:00 am -
1 stop7h 13m
Deal found 9/8![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 10/247:39 pm -
Nonstop2h 01m
Sat 10/319:45 am -
Nonstop1h 54m
Deal found 9/9![American Airlines logo]()
$280
One-way flights from Sioux Falls to ChicagoSearch for one-way flight options from Sioux Falls to Chicago. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
Search for one-way flight options from Sioux Falls to Chicago. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This CheapOair deal was found by Cheapflights users on 9/7. 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$131
This Trip.com deal was found by Cheapflights users on 9/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:52 pm -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$134
This CheapOair deal was found by Cheapflights users on 9/4. 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 9/188:52 pm -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 9/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:52 pm -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$176
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/97:39 pm -
Nonstop2h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Mon 12/711:05 am -
2 stops20h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/28:52 pm -
2 stops20h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/258:52 pm -
2 stops20h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$274
This Delta deal was found by Cheapflights users on 9/7. 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 10/15:05 am -
1 stop3h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 9/8. 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.
Sun 12/2710:57 am -
1 stop6h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 9/251:05 pm -
1 stop5h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$359
Find flight deals from Sioux Falls to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Sioux Falls (FSD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (American Airlines) |
One-way from | $131 (CheapOair) |
Popular in | November |
Cheapest in | January |
Average price | $313 |
Good round-trip deal | $374 or less |
Good one-way deal | $353 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Sioux Falls 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 9, 2026.
Use the filters below to find and compare flights from Sioux Falls 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 - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Fri 10/2
8:52 pm-5:51 pm
2 stops20h 59m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sat 10/10
11:00 am-9:27 pm
1 stop10h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$237
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sun 12/6
3:14 pm-5:14 pm
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Quickest round-trip
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 12/11
7:40 am-9:36 am
Nonstop1h 56m
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
Sat 10/3
5:04 pm-10:46 pm
1 stop5h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Sun 10/11
5:10 am-8:44 am
1 stop3h 34m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Thu 10/8
8:30 am-11:47 am
1 stop3h 17m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - MDW Chicago Midway
FSDMDW
Sioux Falls Joe Foss Field
Wed 11/4
11:00 am-4:47 pm
1 stop5h 47m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Fri 12/4
5:02 pm-9:35 pm
1 stop4h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Sioux FallsChicago
FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl
FSDORD
Sioux Falls Joe Foss Field
Sun 11/8
5:10 am-11:40 am
1 stop6h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Sioux Falls to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sioux Falls to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Sioux Falls-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sioux Falls-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sioux Falls-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Sioux Falls-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sioux Falls-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Sioux Falls to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Sioux Falls with our price prediction graph.
FSD-CHI
FSD-ORD
FSD-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Sioux Falls to Chicago
FSD-CHI
FSD-ORD
FSD-MDW
What is the cheapest month to book a flight from Sioux Falls to Chicago?
Currently, November is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $236). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $364). 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 FSD to CHI?
Find hourly flight availability from Sioux Falls 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 9, 2026.
A simple way to save on the total cost of your ticket is to fly from Sioux Falls to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight at noon.
Weekly flight availability from Sioux Falls to Chicago
Explore weekly flight availability from Sioux Falls 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 9, 2026.
The most flights from FSD to CHI are scheduled on a Monday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Sioux Falls to Chicago?
Airfare is typical for this route at the moment.
Sioux Falls to Chicago flights typically cost between $249 and $358 in October.The cheapest round-trip price found within the last 5 days was $279 on American Airlines (Oct 9-Oct 12).
How far ahead should I book a flight from Sioux Falls to Chicago?
The best time to book flights from Sioux Falls to Chicago is 45 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Sioux Falls to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Sioux Falls to Chicago. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Sioux Falls to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 9, 2026.
Read through reviews of airlines operating flights from Sioux Falls to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Sioux Falls 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
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Sioux Falls and Chicago flights
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Top 2 airlines flying from Sioux Falls to Chicago
Discover the top 2 airlines that operate flights from Sioux Falls 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$276 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$329 | FlexibilityNo cancel fee | On-time69% |