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$97+ Cheap flights from South Dakota to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
mai 12 — mai 191
mar. 5/12
mar. 5/19
1 adult, Economy
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Cheap flight deals from South Dakota to Chicago

Cheapest flights from South Dakota to Chicago
Explore the most affordable flight options available from South Dakota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
lun. 4/206:11 pm
FSD
-
ORD
1 stop27h 06m
Multiple Airlines
jeu. 4/237:15 pm
ORD
-
FSD
1 stop22h 06m
Multiple Airlines
Deal found 4/7$208
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/224:25 pm
FSD
-
ORD
1 stop28h 07m
Frontier
dim. 5/249:37 pm
ORD
-
FSD
1 stop18h 03m
Frontier
Deal found 4/8$221
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/276:11 pm
FSD
-
ORD
1 stop30h 13m
Multiple Airlines
jeu. 4/304:28 pm
ORD
-
FSD
2 stops24h 53m
Multiple Airlines
Deal found 4/9$233
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 4/246:11 pm
FSD
-
ORD
1 stop15h 25m
Multiple Airlines
mar. 4/288:58 pm
ORD
-
FSD
1 stop16h 47m
Multiple Airlines
Deal found 4/9$242
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
jeu. 5/145:57 pm
RAP
-
ORD
2 stops35h 42m
Multiple Airlines
mar. 5/193:55 pm
ORD
-
RAP
1 stop20h 10m
Multiple Airlines
Deal found 4/8$249
This American Airlines deal was found by Cheapflights users on 4/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/76:52 am
FSD
-
ORD
Nonstop2h 02m
American Airlines
jeu. 5/149:11 pm
ORD
-
FSD
Nonstop1h 55m
American Airlines
Deal found 4/7$249
This American Airlines deal was found by Cheapflights users on 4/8. 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.
mer. 5/2012:29 pm
FSD
-
ORD
Nonstop1h 55m
American Airlines
mer. 5/279:04 pm
ORD
-
FSD
Nonstop1h 53m
American Airlines
Deal found 4/8$250
This American Airlines deal was found by Cheapflights users on 4/8. 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.
jeu. 5/76:52 am
FSD
-
ORD
Nonstop2h 02m
American Airlines
dim. 5/106:57 am
ORD
-
FSD
1 stop5h 59m
American Airlines
Deal found 4/8$259
This Kiwi.com deal was found by Cheapflights users on 4/11. 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.
ven. 5/16:11 pm
FSD
-
ORD
1 stop15h 25m
Multiple Airlines
dim. 5/31:00 pm
ORD
-
FSD
1 stop28h 21m
Multiple Airlines
Deal found 4/11$263
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/69:30 am
RAP
-
ORD
Nonstop2h 26m
United Airlines
sam. 5/98:05 pm
ORD
-
RAP
Nonstop2h 41m
United Airlines
Deal found 4/11$269
This Delta deal was found by Cheapflights users on 4/9. 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.
mar. 7/141:30 pm
FSD
-
MDW
1 stop4h 48m
Delta
sam. 8/19:49 am
MDW
-
FSD
1 stop5h 53m
Delta
Deal found 4/9$269
This American Airlines deal was found by Cheapflights users on 4/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 4/3011:53 am
RAP
-
ORD
Nonstop2h 27m
American Airlines
lun. 5/49:45 am
ORD
-
RAP
Nonstop2h 38m
American Airlines
Deal found 4/7$270

Find flight deals from South Dakota to Chicago

Keep the following information in mind while searching for South Dakota to Chicago flight deals. Data was last updated avril 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$344

Good round-trip deal

$348 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Sioux Falls Joe Foss Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sioux Falls Joe Foss Field-Chicago (CHI) flights.
Search Deals
From South Dakota to Chicago (CHI)
Search Deals
One-way flight from South Dakota to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from South Dakota to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from South Dakota to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from South Dakota to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated avril 12, 2026.
Use the filters below to find and compare flights from South Dakota to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

mer. 5/6

9:30 am-12:56 pm

Nonstop2h 26m

Chicago O'Hare Intl

sam. 5/9

8:05 pm-9:46 pm

Nonstop2h 41m

$269

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

ven. 7/3

10:56 am-5:02 pm

1 stop6h 06m

Chicago O'Hare Intl

mer. 7/8

2:07 pm-11:06 pm

2 stops8h 59m

$274

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

ven. 6/5

5:00 am-6:58 am

Nonstop1h 58m

Chicago O'Hare Intl

sam. 6/13

8:09 pm-10:07 pm

Nonstop1h 58m

$281
Quickest round-trip

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

ven. 5/22

5:00 am-6:58 am

Nonstop1h 58m

Chicago O'Hare Intl

dim. 5/24

5:45 pm-7:39 pm

Nonstop1h 54m

$281

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

mer. 7/1

8:23 am-1:09 pm

1 stop4h 46m

Chicago Midway

dim. 7/5

9:54 am-3:44 pm

1 stop5h 50m

$289

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

mer. 5/6

1:44 pm-6:36 pm

1 stop4h 52m

Chicago Midway

mer. 5/13

1:59 pm-7:27 pm

1 stop5h 28m

$289

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

mer. 7/1

8:23 am-11:31 am

1 stop3h 08m

Chicago O'Hare Intl

dim. 7/5

6:30 am-10:16 am

1 stop3h 46m

$289

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

sam. 5/23

4:33 pm-9:20 pm

1 stop3h 47m

Chicago O'Hare Intl

mar. 5/26

5:41 pm-10:24 pm

1 stop5h 43m

$309

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

dim. 5/17

11:13 am-7:20 pm

1 stop7h 07m

Chicago O'Hare Intl

dim. 5/24

5:41 pm-10:24 pm

1 stop5h 43m

$309

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

dim. 5/17

11:13 am-5:56 pm

1 stop5h 43m

Chicago Midway

dim. 5/24

7:13 pm-10:24 pm

1 stop4h 11m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from South Dakota to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from South Dakota with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from South Dakota to Chicago

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

Currently, September is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $169). Flying from South Dakota to Chicago in June is currently the most expensive (average of $221). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SD to CHI?

Find hourly flight availability from South Dakota to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated avril 12, 2026.

One of the essential ways to save on airfare from South Dakota to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 22% on airfare.

What is the cheapest day to fly from South Dakota to Chicago?

Use this chart to determine the cheapest time to fly round-trip from South Dakota to Chicago. Price data was last updated on April 11, 2026.

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

Weekly flight availability from South Dakota to Chicago

Explore weekly flight availability from South Dakota to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated avril 12, 2026.

The most flights from USSD to CHI are scheduled on a Thursday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 on average).

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

Related info for your journey

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

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

    Airlines like United Airlines and Delta fly from South Dakota to Chicago in about 2h 26m. The time it takes to get you to your destination can typically vary by up to 3h 40m. The distance from South Dakota to Chicago is about 777 mi. This flight may include one or multiple stops.

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

    When deciding which route to take from South Dakota to Chicago consider Sioux Falls Joe Foss Field - Chicago O'Hare Intl, Sioux Falls Joe Foss Field - Chicago Midway or Rapid City - Chicago O'Hare Intl as they are the most popular.

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

    The top 3 most reliable airlines when flying from South Dakota to Chicago are Qatar Airways (84%), Copa Airlines (77%) and Envoy Air (76%).

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

    On average you can expect to pay $1,023 for a flight from South Dakota to Chicago. The cheapest flight overall is $188 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $249.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from South Dakota to Chicago 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 South Dakota to Chicago?

    Currently, September is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $169). Flying from South Dakota to Chicago in June is currently the most expensive (average of $221). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
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Alternative routes for South Dakota to Chicago

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

Discover the top 2 airlines that operate flights from South Dakota to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated avril 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$288FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$335FlexibilityNo cancel feeOn-time69%

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