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$103+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
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 February 16, 2026.

This Delta deal was found by Cheapflights users on 2/15. 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.
Mon 4/131:44 pm
FSD
-
MDW
1 stop4h 52m
Delta
Sat 4/187:16 pm
MDW
-
FSD
1 stop3h 46m
Delta
Deal found 2/15$177
This Delta deal was found by Cheapflights users on 2/13. 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 10/2410:58 am
FSD
-
ORD
1 stop3h 59m
Delta
Mon 10/265:20 pm
ORD
-
FSD
1 stop5h 31m
Delta
Deal found 2/13$177
This Delta deal was found by Cheapflights users on 2/13. 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 6/308:15 am
FSD
-
ORD
1 stop6h 43m
Delta
Fri 7/31:35 pm
ORD
-
FSD
2 stops9h 11m
Delta
Deal found 2/13$182
This Delta deal was found by Cheapflights users on 2/15. 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.
Mon 4/131:44 pm
FSD
-
ORD
2 stops10h 15m
Delta
Sat 4/185:04 pm
ORD
-
FSD
2 stops5h 58m
Delta
Deal found 2/15$187
This American Airlines deal was found by Cheapflights users on 2/14. 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 10/247:18 am
FSD
-
ORD
Nonstop1h 52m
American Airlines
Mon 10/268:20 pm
ORD
-
FSD
Nonstop1h 57m
American Airlines
Deal found 2/14$189
This Delta deal was found by Cheapflights users on 2/13. 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 7/28:15 am
FSD
-
MDW
1 stop4h 52m
Delta
Wed 7/81:00 pm
MDW
-
FSD
2 stops9h 46m
Delta
Deal found 2/13$198
This Delta deal was found by Cheapflights users on 2/15. 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 4/161:44 pm
FSD
-
ORD
1 stop6h 08m
Delta
Sat 4/185:04 pm
ORD
-
FSD
2 stops5h 58m
Delta
Deal found 2/15$198
This United Airlines deal was found by Cheapflights users on 2/14. 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 3/203:10 pm
FSD
-
ORD
Nonstop1h 50m
United Airlines
Tue 3/248:10 pm
ORD
-
FSD
Nonstop1h 52m
United Airlines
Deal found 2/14$199
This United Airlines deal was found by Cheapflights users on 2/14. 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 3/67:43 am
FSD
-
ORD
Nonstop1h 52m
United Airlines
Sun 3/88:10 pm
ORD
-
FSD
Nonstop1h 52m
United Airlines
Deal found 2/14$204
This American Airlines deal was found by Cheapflights users on 2/14. 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 4/711:53 am
RAP
-
ORD
Nonstop2h 27m
American Airlines
Mon 4/139:45 am
ORD
-
RAP
Nonstop2h 38m
American Airlines
Deal found 2/14$209
This American Airlines deal was found by Cheapflights users on 2/14. 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 5/17:39 pm
FSD
-
ORD
Nonstop1h 55m
American Airlines
Sun 5/310:05 am
ORD
-
FSD
Nonstop1h 54m
American Airlines
Deal found 2/14$209
This American Airlines deal was found by Cheapflights users on 2/15. 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 4/911:53 am
RAP
-
ORD
Nonstop2h 27m
American Airlines
Mon 4/139:45 am
ORD
-
RAP
Nonstop2h 38m
American Airlines
Deal found 2/15$210

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 February 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Delta)

One-way from

$103
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$289

Good round-trip deal

$339 or less

Good one-way deal

$245 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. 7% potential increase in price ($24 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 February 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 February 16, 2026.
Use the filters below to find and compare flights from South Dakota to Chicago that are best for you.

Fly from

South Dakota

Fly to

Chicago

Route

Depart

Return

Price

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Tue 4/14

5:00 am-8:46 am

1 stop3h 46m

Chicago Midway

Sat 4/18

7:16 pm-11:02 pm

1 stop3h 46m

$177

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Mon 4/13

1:44 pm-7:52 pm

1 stop6h 08m

Chicago O'Hare Intl

Thu 4/16

7:09 pm-11:02 pm

1 stop3h 53m

$177

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 3/25

7:43 am-9:35 am

Nonstop1h 52m

Chicago O'Hare Intl

Sat 3/28

8:10 pm-10:02 pm

Nonstop1h 52m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 3/20

6:35 pm-8:25 pm

Nonstop1h 50m

Chicago O'Hare Intl

Tue 3/24

8:10 pm-10:02 pm

Nonstop1h 52m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sun 3/29

6:35 pm-8:32 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 4/26

7:58 pm-9:49 pm

Nonstop1h 51m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 4/16

1:44 pm-7:52 pm

1 stop6h 08m

Chicago O'Hare Intl

Sat 4/18

7:07 pm-11:02 pm

1 stop3h 55m

$193

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 7/2

8:15 am-1:07 pm

1 stop4h 52m

Chicago Midway

Wed 7/8

1:00 pm-10:46 pm

2 stops9h 46m

$198

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 3/7

7:43 am-9:35 am

Nonstop1h 52m

Chicago O'Hare Intl

Tue 3/10

8:10 pm-10:02 pm

Nonstop1h 52m

$204

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 3/6

7:43 am-9:35 am

Nonstop1h 52m

Chicago O'Hare Intl

Sun 3/8

8:10 pm-10:02 pm

Nonstop1h 52m

$204

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 5/23

3:32 pm-7:05 pm

Nonstop2h 33m

Chicago O'Hare Intl

Fri 5/29

1:28 pm-3:02 pm

Nonstop2h 34m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 59 results
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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, March is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $187). Flying from South Dakota to Chicago in June is currently the most expensive (average of $224). 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 February 16, 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 25% 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 February 7, 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. Saturday 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 February 16, 2026.

The most flights from USSD to CHI are scheduled on a Friday (23 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 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 Delta, United Airlines, and American Airlines fly from South Dakota to Chicago in about 1h 52m. The time it takes to get you to your destination can typically vary by up to 1h 54m. The distance from South Dakota to Chicago is about 461 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 Envoy Air (74%), Republic Airways (70%) and Copa Airlines (70%).

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

    On average you can expect to pay $923 for a flight from South Dakota to Chicago. The cheapest flight overall is $155 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $177.

  • 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, March is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $187). Flying from South Dakota to Chicago in June is currently the most expensive (average of $224). 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
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Hammond
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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 3 airlines flying from South Dakota to Chicago

Discover the top 3 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 February 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$178Average$289FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$220FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$327FlexibilityNo cancel feeOn-time69%

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