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South Dakota

$126+ Cheap flights from Chicago (CHI) to South Dakota

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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RAP
Jun 25 — Jul 21
Thu 6/25
Thu 7/2
1 adult, Economy
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Cheap flight deals from Chicago to South Dakota

Cheapest flights from Chicago to South Dakota
Explore the most affordable flight options available from Chicago to South Dakota. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 26, 2026.

This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/242:19 pm
ORD
-
FSD
Nonstop1h 54m
American Airlines
Tue 8/412:00 pm
FSD
-
ORD
Nonstop1h 54m
American Airlines
Deal found 5/25$249
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:40 am
ORD
-
FSD
Nonstop1h 54m
American Airlines
Sun 6/217:02 am
FSD
-
ORD
Nonstop2h 03m
American Airlines
Deal found 5/25$250
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:43 am
ORD
-
RAP
Nonstop2h 32m
American Airlines
Wed 8/2612:20 pm
RAP
-
ORD
Nonstop2h 29m
American Airlines
Deal found 5/25$251
This United Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:45 am
ORD
-
RAP
Nonstop2h 39m
United Airlines
Wed 7/226:00 am
RAP
-
ORD
Nonstop2h 34m
United Airlines
Deal found 5/24$260
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/113:52 pm
ORD
-
RAP
1 stop6h 39m
American Airlines
Wed 7/153:26 pm
RAP
-
ORD
Nonstop2h 34m
American Airlines
Deal found 5/25$261
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/122:15 pm
ORD
-
FSD
Nonstop1h 55m
American Airlines
Mon 6/157:02 am
FSD
-
ORD
Nonstop2h 03m
American Airlines
Deal found 5/24$264
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/176:00 am
ORD
-
FSD
1 stop4h 00m
Delta
Sun 9/205:15 am
FSD
-
ORD
1 stop3h 19m
Delta
Deal found 5/21$269
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/99:30 pm
ORD
-
RAP
Nonstop2h 46m
United Airlines
Mon 7/136:00 am
RAP
-
ORD
Nonstop2h 34m
United Airlines
Deal found 5/21$269
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/136:55 pm
MDW
-
FSD
1 stop3h 59m
Delta
Mon 6/155:15 am
FSD
-
MDW
1 stop3h 22m
Delta
Deal found 5/21$269
This United Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:00 am
ORD
-
RAP
1 stop5h 20m
United Airlines
Tue 6/231:35 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Deal found 5/23$270
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:25 pm
MDW
-
RAP
1 stop4h 12m
Delta
Tue 8/116:48 am
RAP
-
MDW
1 stop5h 22m
Delta
Deal found 5/24$271
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/122:15 pm
ORD
-
FSD
Nonstop1h 55m
American Airlines
Sun 6/147:02 am
FSD
-
ORD
Nonstop2h 03m
American Airlines
Deal found 5/25$279

Find flight deals from Chicago to South Dakota

Keep the following information in mind while searching for Chicago to South Dakota flight deals. Data was last updated May 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$126
(Mytrip)

Popular in

April

Cheapest in

January

Average price

$339

Good round-trip deal

$282 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Chicago (CHI)-Sioux Falls Joe Foss Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Sioux Falls Joe Foss Field flights.
Search Deals
From Chicago (CHI) to South Dakota
Search Deals
One-way flight from Chicago (CHI) to South Dakota
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to South Dakota.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to South Dakota.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to South Dakota 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 May 26, 2026.
Use the filters below to find and compare flights from Chicago to South Dakota that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Fri 7/24

9:30 pm-11:16 pm

Nonstop2h 46m

Rapid City

Wed 7/29

1:35 pm-4:59 pm

Nonstop2h 24m

$260
Quickest round-trip

ChicagoSioux Falls

ORD - FSD

ORDFSD

Chicago O'Hare Intl

Wed 6/10

7:45 pm-9:43 pm

Nonstop1h 58m

Sioux Falls Joe Foss Field

Sat 6/20

7:40 am-9:36 am

Nonstop1h 56m

$264

ChicagoSioux Falls

MDW - FSD

MDWFSD

Chicago Midway

Sat 7/4

1:49 pm-7:38 pm

1 stop5h 49m

Sioux Falls Joe Foss Field

Sat 7/11

1:13 pm-5:52 pm

1 stop4h 39m

$269

ChicagoSioux Falls

MDW - FSD

MDWFSD

Chicago Midway

Sat 6/13

6:55 pm-10:54 pm

1 stop3h 59m

Sioux Falls Joe Foss Field

Mon 6/15

5:15 am-8:37 am

1 stop3h 22m

$269

ChicagoRapid City

MDW - RAP

MDWRAP

Chicago Midway

Tue 8/4

7:25 pm-10:37 pm

1 stop4h 12m

Rapid City

Tue 8/11

6:48 am-1:10 pm

1 stop5h 22m

$271

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Thu 7/9

5:00 am-9:19 am

1 stop5h 19m

Rapid City

Mon 7/13

6:00 am-9:34 am

Nonstop2h 34m

$279

ChicagoSioux Falls

ORD - FSD

ORDFSD

Chicago O'Hare Intl

Fri 6/12

5:57 pm-11:12 pm

1 stop5h 15m

Sioux Falls Joe Foss Field

Mon 6/15

1:53 pm-7:31 pm

1 stop5h 38m

$284

ChicagoSioux Falls

MDW - FSD

MDWFSD

Chicago Midway

Fri 6/12

7:16 pm-11:12 pm

1 stop3h 56m

Sioux Falls Joe Foss Field

Mon 6/15

1:53 pm-6:18 pm

1 stop4h 25m

$284

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Tue 9/15

8:58 am-10:26 am

Nonstop2h 28m

Rapid City

Tue 9/22

5:47 pm-11:59 pm

1 stop5h 12m

$304

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Thu 8/20

8:58 am-10:26 am

Nonstop2h 28m

Rapid City

Sun 8/30

1:31 pm-4:55 pm

Nonstop2h 24m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to South Dakota

Have a flexible travel schedule? Discover the best time to fly to South Dakota from Chicago with our price prediction graph.
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 Chicago to South Dakota

What is the cheapest month to book a flight from Chicago to South Dakota?

Currently, May is the cheapest month in which you can book a flight from Chicago to South Dakota (average of $168). Flying from Chicago to South Dakota in April is currently the most expensive (average of $209). 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 CHI to SD?

Find hourly flight availability from Chicago to South Dakota. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 26, 2026.

It’s optimal to fly from Chicago to South Dakota in the afternoon. By choosing this option you can save up to 5% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Chicago to South Dakota

Explore weekly flight availability from Chicago to South Dakota. 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 May 26, 2026.

The most flights from CHI to USSD are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Chicago to South Dakota?

How far ahead should I book a flight from Chicago to South Dakota?

The best time to book flights from Chicago to South Dakota is 81 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 Chicago to South Dakota?

Use this chart to determine the cheapest time to fly round-trip from Chicago to South Dakota. Price data was last updated on April 4, 2026.

Travelers seeking maximum savings on their Chicago to South Dakota flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing South Dakota

Get insights into the airlines that provide service to South Dakota. 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 South Dakota. Reviews last updated May 26, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Chicago to South Dakota by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,425 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.9
Good
8,425 reviews
Delta
7.9
Good
8,425 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
9,749 reviews
Delta
7.9
Good
8,425 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,629 reviews
Delta
7.9
Good
8,425 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Comfort

7.8

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Related info for your journey

Find useful and relevant information for your journey from Chicago to South Dakota. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to South Dakota?

    For as low as $260, United Airlines can have you in South Dakota from Chicago in 2h 46m. The distance from Chicago to South Dakota is about 777 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to South Dakota one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $138. American Airlines flights start at $148 while deals on Delta start at $279 one-way.

  • What are the most popular routes from Chicago to South Dakota?

    The most popular route from Chicago to South Dakota is Chicago O'Hare Intl - Rapid City. You may also consider Chicago O'Hare Intl - Sioux Falls Joe Foss Field or Chicago Midway - Rapid City.

  • What are the most reliable airlines from Chicago to South Dakota?

    The top 3 most reliable airlines when flying from Chicago to South Dakota are American Airlines (82%), Envoy Air (82%) and SkyWest Airlines (68%).

  • What are the cheapest flights from Chicago to South Dakota?

    On average you can expect to pay $298 for a flight from Chicago to South Dakota. The cheapest flight overall is $159 while the most popular route, (Chicago O'Hare Intl - Rapid City) is currently priced at $251.

  • Can I find deals for flights from Chicago to South Dakota that include hotel bookings?

    Yes. In addition to deals on Chicago to South Dakota flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to South Dakota?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to South Dakota.

  • Can I find deals for business class flights from Chicago to South Dakota?

    Yes. Cheapflights offers flight deals from Chicago to South Dakota by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to South Dakota?

    Currently, May is the cheapest month in which you can book a flight from Chicago to South Dakota (average of $168). Flying from Chicago to South Dakota in April is currently the most expensive (average of $209). 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.

See more FAQs

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Alternative routes for Chicago to South Dakota

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to South Dakota

Discover the top 2 airlines that operate flights from Chicago to South Dakota. 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 May 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$317FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$369FlexibilityNo cancel feeOn-time69%

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