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South Dakota

$125+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RAP
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 10, 2026.

This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:30 pm
ORD
-
RAP
Nonstop2h 46m
United Airlines
Wed 7/291:35 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Deal found 5/7$191
This Delta deal was found by Cheapflights users on 5/6. 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 7/116:25 pm
ORD
-
RAP
1 stop5h 01m
Delta
Wed 7/152:31 pm
RAP
-
ORD
1 stop3h 59m
Delta
Deal found 5/6$211
This United Airlines deal was found by Cheapflights users on 5/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:30 pm
ORD
-
RAP
Nonstop2h 46m
United Airlines
Wed 7/85:53 pm
RAP
-
ORD
1 stop5h 51m
United Airlines
Deal found 5/10$217
This Delta deal was found by Cheapflights users on 5/6. 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 7/116:55 pm
MDW
-
RAP
1 stop4h 31m
Delta
Sat 7/186:48 am
RAP
-
MDW
1 stop5h 21m
Delta
Deal found 5/6$221
This United Airlines deal was found by Cheapflights users on 5/9. 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.
Sat 6/139:30 pm
ORD
-
RAP
Nonstop2h 46m
United Airlines
Mon 6/151:35 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Deal found 5/9$222
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 8/291:25 pm
ORD
-
RAP
Nonstop2h 31m
American Airlines
Sat 9/512:19 pm
RAP
-
ORD
Nonstop2h 30m
American Airlines
Deal found 5/10$231
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Wed 8/196:00 am
ORD
-
RAP
1 stop6h 49m
American Airlines
Sat 8/2912:19 pm
RAP
-
ORD
Nonstop2h 30m
American Airlines
Deal found 5/6$232
This United Airlines deal was found by Cheapflights users on 5/8. 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 6/245:00 am
ORD
-
RAP
1 stop5h 20m
United Airlines
Wed 7/16:00 am
RAP
-
ORD
Nonstop2h 34m
United Airlines
Deal found 5/8$234
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:30 pm
ORD
-
RAP
Nonstop2h 46m
United Airlines
Wed 6/105:53 pm
RAP
-
ORD
1 stop5h 51m
United Airlines
Deal found 5/5$240
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Tue 9/225:00 am
ORD
-
RAP
1 stop6h 49m
American Airlines
Tue 9/296:11 pm
RAP
-
ORD
Nonstop2h 19m
American Airlines
Deal found 5/6$241
This Delta deal was found by Cheapflights users on 5/6. 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 10/2312:30 pm
MDW
-
RAP
1 stop4h 16m
Delta
Sat 10/2411:30 am
RAP
-
MDW
1 stop4h 20m
Delta
Deal found 5/6$242
This Delta deal was found by Cheapflights users on 5/6. 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 10/239:30 am
ORD
-
RAP
1 stop7h 16m
Delta
Sat 10/2411:30 am
RAP
-
ORD
1 stop4h 19m
Delta
Deal found 5/6$242

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 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$191
(United Airlines)

One-way from

$125
(Mytrip)

Popular in

April

Cheapest in

January

Average price

$284

Good round-trip deal

$249 or less

Good one-way deal

$168 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. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 10, 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

Sat 6/13

9:30 pm-11:16 pm

Nonstop2h 46m

Rapid City

Mon 6/15

1:35 pm-4:59 pm

Nonstop2h 24m

$222

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

Sun 6/14

7:40 am-9:36 am

Nonstop1h 56m

$249

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Tue 8/11

8:44 am-10:12 am

Nonstop2h 28m

Rapid City

Sat 8/15

6:00 am-9:36 am

Nonstop2h 36m

$249

ChicagoSioux Falls

ORD - FSD

ORDFSD

Chicago O'Hare Intl

Wed 6/3

6:24 am-10:15 am

1 stop3h 51m

Sioux Falls Joe Foss Field

Sat 6/6

4:17 pm-9:20 pm

1 stop5h 03m

$269

ChicagoSioux Falls

MDW - FSD

MDWFSD

Chicago Midway

Fri 8/21

7:25 pm-10:51 pm

1 stop3h 26m

Sioux Falls Joe Foss Field

Mon 8/24

5:04 am-8:40 am

1 stop3h 36m

$269

ChicagoSioux Falls

ORD - FSD

ORDFSD

Chicago O'Hare Intl

Wed 6/3

6:24 am-10:15 am

1 stop3h 51m

Sioux Falls Joe Foss Field

Wed 6/10

1:53 pm-8:31 pm

2 stops6h 38m

$274

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Fri 7/24

7:05 am-3:29 pm

2 stops9h 24m

Rapid City

Mon 7/27

6:48 am-3:05 pm

1 stop7h 17m

$278

ChicagoSioux Falls

ORD - FSD

ORDFSD

Chicago O'Hare Intl

Tue 6/30

9:30 pm-11:31 pm

Nonstop2h 01m

Sioux Falls Joe Foss Field

Sun 7/5

7:40 am-9:36 am

Nonstop1h 56m

$279

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Fri 7/3

8:36 am-2:19 pm

1 stop6h 43m

Rapid City

Wed 7/8

11:00 am-4:59 pm

1 stop4h 59m

$283

ChicagoRapid City

ORD - RAP

ORDRAP

Chicago O'Hare Intl

Thu 6/4

9:30 pm-11:16 pm

Nonstop2h 46m

Rapid City

Thu 6/11

1:35 pm-4:59 pm

Nonstop2h 24m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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 77 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 month to book a flight from Chicago to South Dakota?

Currently, June is the cheapest month in which you can book a flight from Chicago to South Dakota (average of $169). 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 10, 2026.

It’s optimal to fly from Chicago to South Dakota at noon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the evening.

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.

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 10, 2026.

The most flights from CHI to USSD are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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

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 10, 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
8,455 reviews

Boarding

8.1

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

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
8,455 reviews
Delta
7.9
Good
8,455 reviews

Boarding

8.1

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

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
9,694 reviews
Delta
7.9
Good
8,455 reviews

Boarding

8.1

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

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
11,667 reviews
Delta
7.9
Good
8,455 reviews

Boarding

8.1

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

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 $222, 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 American Airlines, which is currently one of the cheapest options available, starting at $138. United Airlines flights start at $144 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 - Sioux Falls Joe Foss Field.

  • 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 SkyWest Airlines (88%), American Airlines (76%) and Envoy Air (76%).

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

    On average you can expect to pay $307 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 $201.

  • 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, June is the cheapest month in which you can book a flight from Chicago to South Dakota (average of $169). 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 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$310FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$365FlexibilityNo cancel feeOn-time69%

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