$126+ Cheap flights from Sioux Falls (FSD) 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Jul 12 — Jul 191
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 December, booked 84 days in advance, depart on a Friday 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 June 12, 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 June 12, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 7/36:28 pm
FSD
- ORD
Nonstop1h 58m
United Airlines
Fri 7/109:30 pm
ORD
- FSD
Nonstop2h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 7/212:02 pm
FSD
- ORD
Nonstop1h 58m
American Airlines
Sun 7/510:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/9![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:34 pm
FSD
- ORD
1 stop7h 16m
American Airlines
Wed 7/82:30 pm
ORD
- FSD
Nonstop1h 54m
American Airlines
Deal found 6/10![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:34 pm
FSD
- ORD
1 stop7h 16m
American Airlines
Sun 8/210:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 7/36:28 pm
FSD
- ORD
Nonstop1h 58m
United Airlines
Mon 7/69:30 pm
ORD
- FSD
Nonstop2h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/267:02 am
FSD
- ORD
Nonstop2h 03m
American Airlines
Sun 7/510:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 6/10. 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 9/111:20 pm
FSD
- MDW
1 stop4h 45m
Delta
Sun 9/136:45 pm
MDW
- FSD
1 stop4h 01m
Delta
Deal found 6/10![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/35:12 am
FSD
- ORD
1 stop3h 23m
Delta
Wed 7/86:30 am
ORD
- FSD
1 stop6h 19m
Delta
Deal found 6/12![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 9/510:54 am
FSD
- MDW
1 stop5h 03m
Delta
Tue 9/86:45 pm
MDW
- FSD
1 stop4h 01m
Delta
Deal found 6/7![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/7. 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 7/38:23 am
FSD
- ORD
1 stop6h 42m
Delta
Sun 7/56:30 am
ORD
- FSD
1 stop3h 46m
Delta
Deal found 6/7![Delta logo]()
$279
This CheapOair deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/288:14 pm
FSD
- ORD
1 stop24h 39m
Frontier
Sun 8/309:48 pm
ORD
- FSD
1 stop21h 31m
Frontier
Deal found 6/12![Frontier logo]()
$280
This Delta deal was found by Cheapflights users on 6/10. 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 6/261:53 pm
FSD
- MDW
1 stop4h 25m
Delta
Sun 7/57:16 pm
MDW
- FSD
1 stop3h 56m
Delta
Deal found 6/10![Delta logo]()
$284
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 June 12, 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 June 12, 2026.
This Delta deal was found by Cheapflights users on 6/9. 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 9/510:54 am
FSD
- MDW
1 stop5h 03m
Delta
Tue 9/86:45 pm
MDW
- FSD
1 stop4h 01m
Delta
Deal found 6/9![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/247:35 am
FSD
- ORD
Nonstop1h 56m
United Airlines
Sun 7/269:30 pm
ORD
- FSD
Nonstop2h 01m
United Airlines
Deal found 6/8![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 9/510:54 am
FSD
- MDW
1 stop5h 03m
Delta
Sat 9/129:20 am
MDW
- FSD
1 stop6h 08m
Delta
Deal found 6/7![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/8. 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 7/38:23 am
FSD
- ORD
1 stop6h 42m
Delta
Wed 7/86:30 am
ORD
- FSD
1 stop6h 19m
Delta
Deal found 6/8![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/7. 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.
Wed 7/15:12 am
FSD
- ORD
1 stop3h 23m
Delta
Sun 7/56:30 am
ORD
- FSD
1 stop3h 46m
Delta
Deal found 6/7![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/9. 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.
Fri 8/75:00 am
FSD
- ORD
1 stop3h 30m
Delta
Sun 8/96:00 am
ORD
- FSD
1 stop6h 38m
Delta
Deal found 6/9![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 10/31:05 pm
FSD
- MDW
1 stop5h 06m
Delta
Sun 10/41:47 pm
MDW
- FSD
1 stop5h 56m
Delta
Deal found 6/12![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/185:45 pm
FSD
- ORD
1 stop4h 07m
Delta
Wed 7/225:54 pm
ORD
- FSD
1 stop5h 12m
Delta
Deal found 6/11![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/181:13 pm
FSD
- MDW
1 stop4h 39m
Delta
Wed 7/227:06 pm
MDW
- FSD
1 stop4h 00m
Delta
Deal found 6/11![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 6/10. 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 9/45:00 am
FSD
- MDW
1 stop3h 39m
Delta
Mon 9/77:25 pm
MDW
- FSD
1 stop3h 26m
Delta
Deal found 6/10![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 6/8. 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 9/41:26 pm
FSD
- ORD
1 stop3h 33m
Delta
Mon 9/76:00 am
ORD
- FSD
1 stop6h 38m
Delta
Deal found 6/8![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/298:23 am
FSD
- MDW
1 stop4h 46m
Delta
Sat 8/19:54 am
MDW
- FSD
1 stop5h 47m
Delta
Deal found 6/11![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 6/10. 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 9/48:22 am
FSD
- MDW
2 stops10h 11m
Delta
Thu 9/106:45 pm
MDW
- FSD
1 stop4h 01m
Delta
Deal found 6/10![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 6/10. 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 9/45:00 am
FSD
- ORD
2 stops8h 08m
Delta
Thu 9/105:20 pm
ORD
- FSD
1 stop5h 26m
Delta
Deal found 6/10![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/185:00 am
FSD
- MDW
1 stop3h 39m
Delta
Thu 8/209:59 am
MDW
- FSD
1 stop5h 49m
Delta
Deal found 6/11![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 6/9. 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.
Tue 8/188:22 am
FSD
- MDW
1 stop4h 48m
Delta
Fri 8/211:51 pm
MDW
- FSD
1 stop5h 38m
Delta
Deal found 6/9![Delta logo]()
$517
Last-minute flights from Sioux Falls to ChicagoDiscover last-minute flight deals from Sioux Falls to Chicago. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Sioux Falls to Chicago. Data last updated June 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/10. 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 6/231:53 pm
FSD
- MDW
1 stop4h 25m
Delta
Sat 6/271:49 pm
MDW
- FSD
1 stop5h 49m
Delta
Deal found 6/10![Delta logo]()
$299
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:40 pm
FSD
- ORD
Nonstop2h 04m
American Airlines
Sun 7/510:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/10![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 6/10. 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 6/261:53 pm
FSD
- MDW
1 stop4h 25m
Delta
Sun 7/57:16 pm
MDW
- FSD
1 stop3h 56m
Delta
Deal found 6/10![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/8. 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 7/15:12 am
FSD
- MDW
1 stop3h 25m
Delta
Fri 7/37:16 pm
MDW
- FSD
1 stop3h 56m
Delta
Deal found 6/8![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 7/212:02 pm
FSD
- ORD
Nonstop1h 58m
American Airlines
Sun 7/510:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/9![American Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 7/36:28 pm
FSD
- ORD
Nonstop1h 58m
United Airlines
Fri 7/109:30 pm
ORD
- FSD
Nonstop2h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:34 pm
FSD
- ORD
1 stop7h 16m
American Airlines
Wed 7/82:30 pm
ORD
- FSD
Nonstop1h 54m
American Airlines
Deal found 6/10![American Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 7/36:28 pm
FSD
- ORD
Nonstop1h 58m
United Airlines
Mon 7/69:30 pm
ORD
- FSD
Nonstop2h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/35:12 am
FSD
- ORD
1 stop3h 23m
Delta
Wed 7/86:30 am
ORD
- FSD
1 stop6h 19m
Delta
Deal found 6/12![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/8. 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 7/35:12 am
FSD
- ORD
1 stop3h 23m
Delta
Sat 7/412:46 pm
ORD
- FSD
1 stop6h 52m
Delta
Deal found 6/8![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/181:13 pm
FSD
- MDW
1 stop4h 39m
Delta
Tue 7/217:06 pm
MDW
- FSD
1 stop4h 00m
Delta
Deal found 6/11![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:34 pm
FSD
- ORD
1 stop7h 16m
American Airlines
Sun 8/210:30 pm
ORD
- FSD
Nonstop1h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$260
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 June 12, 2026.
Search for one-way flight options from Sioux Falls to Chicago. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This Booking.com deal was found by Cheapflights users on 6/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:08 pm
FSD
- ORD
1 stop24h 44m
Frontier
Deal found 6/8![Frontier logo]()
$126
This CheapOair deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/108:08 pm
FSD
- ORD
1 stop24h 44m
Frontier
Deal found 6/11![Frontier logo]()
$140
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:14 pm
FSD
- ORD
1 stop24h 29m
Frontier
Deal found 6/11![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:39 pm
FSD
- ORD
1 stop13h 58m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$164
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:08 pm
FSD
- ORD
1 stop24h 44m
Frontier
Deal found 6/10![Frontier logo]()
$166
This Booking.com deal was found by Cheapflights users on 6/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:14 pm
FSD
- ORD
1 stop24h 29m
Frontier
Deal found 6/8![Frontier logo]()
$167
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/94:43 pm
FSD
- ORD
Nonstop2h 05m
American Airlines
Deal found 6/11![American Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/1011:42 am
FSD
- ORD
2 stops42h 35m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$171
This United Airlines deal was found by Cheapflights users on 6/8. 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 9/26:38 pm
FSD
- ORD
Nonstop1h 57m
United Airlines
Deal found 6/8![United Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/109:57 am
FSD
- MDW
2 stops30h 54m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sun 7/56:36 pm
FSD
- MDW
2 stops20h 02m
Allegiant Air
Deal found 6/7![Allegiant Air logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:40 pm
FSD
- MDW
2 stops37h 11m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$227
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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (American Airlines) |
One-way from | $126 (Booking.com) |
Popular in | July |
Cheapest in | January |
Average price | $329 |
Good round-trip deal | $400 or less |
Good one-way deal | $303 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 2,558,603 searches. Data last updated June 12, 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 - MDW
FSDMDW
Sioux Falls Joe Foss Field
Sat 9/5
10:54 am-3:57 pm
1 stop5h 03m
Chicago Midway
Tue 9/8
6:45 pm-10:46 pm
1 stop4h 01m
$279
Sioux FallsChicago
FSD - MDW
FSDMDW
Sioux Falls Joe Foss Field
Sat 9/5
10:54 am-3:57 pm
1 stop5h 03m
Chicago Midway
Sat 9/12
9:20 am-3:28 pm
1 stop6h 08m
$279
Sioux FallsChicago
FSD - ORD
FSDORD
Sioux Falls Joe Foss Field
Fri 7/3
8:23 am-3:05 pm
1 stop6h 42m
Chicago O'Hare Intl
Wed 7/8
6:30 am-12:49 pm
1 stop6h 19m
$279
Sioux FallsChicago
FSD - ORD
FSDORD
Sioux Falls Joe Foss Field
Wed 7/1
5:12 am-8:35 am
1 stop3h 23m
Chicago O'Hare Intl
Sun 7/5
6:30 am-10:16 am
1 stop3h 46m
$279
Sioux FallsChicago
FSD - ORD
FSDORD
Sioux Falls Joe Foss Field
Fri 8/7
5:00 am-8:30 am
1 stop3h 30m
Chicago O'Hare Intl
Sun 8/9
6:00 am-12:38 pm
1 stop6h 38m
$279
Sioux FallsChicago
FSD - MDW
FSDMDW
Sioux Falls Joe Foss Field
Sat 10/3
1:05 pm-6:11 pm
1 stop5h 06m
Chicago Midway
Sun 10/4
1:47 pm-7:43 pm
1 stop5h 56m
$284
Sioux FallsChicago
FSD - ORD
FSDORD
Sioux Falls Joe Foss Field
Sat 7/18
5:45 pm-9:52 pm
1 stop4h 07m
Chicago O'Hare Intl
Wed 7/22
5:54 pm-11:06 pm
1 stop5h 12m
$284
Quickest round-trip
Sioux FallsChicago
FSD - ORD
FSDORD
Sioux Falls Joe Foss Field
Fri 7/24
7:35 am-9:31 am
Nonstop1h 56m
Chicago O'Hare Intl
Sun 7/26
9:30 pm-11:31 pm
Nonstop2h 01m
$301
Sioux FallsChicago
FSD - MDW
FSDMDW
Sioux Falls Joe Foss Field
Sat 7/18
1:13 pm-5:52 pm
1 stop4h 39m
Chicago Midway
Wed 7/22
7:06 pm-11:06 pm
1 stop4h 00m
$344
Sioux FallsChicago
FSD - MDW
FSDMDW
Sioux Falls Joe Foss Field
Fri 9/4
5:00 am-8:39 am
1 stop3h 39m
Chicago Midway
Mon 9/7
7:25 pm-10:51 pm
1 stop3h 26m
$369
Showing 1-10 of 37 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 June.
| 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-MDW
FSD-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 Sioux Falls to Chicago
FSD-CHI
FSD-MDW
FSD-ORD
What is the cheapest month to book a flight from Sioux Falls to Chicago?
Currently, April is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $151). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $245). 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 June 12, 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 21% on your trip compared to booking a flight in the afternoon.
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 June 12, 2026.
The most flights from FSD to CHI are scheduled on a Wednesday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Sioux Falls to Chicago?
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 38 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 June 8, 2026.
Travelers seeking maximum savings on their Sioux Falls to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Tuesday 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 June 12, 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.
Food
7.2
Entertainment
7.8
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Entertainment
7.8
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Entertainment
7.8
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Entertainment
7.8
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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
Lansing
Merrillville
Hammond
Porter
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Sioux Falls and Chicago flights
Browse other Sioux Falls and Chicago flight options. Last updated on June 12, 2026.
Other flights from Sioux Falls
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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 2,558,603 searches. Data last updated June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$249 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$322 | FlexibilityNo cancel fee | On-time69% |