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$131+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
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 June 22, 2026.

This CheapOair deal was found by Cheapflights users on 6/20. 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 7/278:08 pm
FSD
-
ORD
1 stop24h 44m
Frontier
Tue 8/49:57 pm
ORD
-
FSD
1 stop21h 26m
Frontier
Deal found 6/20$235
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Mon 8/37:06 am
FSD
-
ORD
Nonstop1h 59m
American Airlines
Mon 8/1010:40 pm
ORD
-
FSD
Nonstop1h 50m
American Airlines
Deal found 6/19$248
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Fri 9/46:39 pm
FSD
-
ORD
Nonstop1h 59m
United Airlines
Mon 9/79:30 pm
ORD
-
FSD
Nonstop1h 52m
United Airlines
Deal found 6/21$249
This CheapOair deal was found by Cheapflights users on 6/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:31 pm
FSD
-
ORD
1 stop26h 04m
Frontier
Sun 9/1310:40 pm
ORD
-
FSD
1 stop19h 56m
Frontier
Deal found 6/21$250
This American Airlines deal was found by Cheapflights users on 6/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:34 pm
FSD
-
ORD
1 stop7h 16m
American Airlines
Sun 7/1910:30 pm
ORD
-
FSD
Nonstop1h 48m
American Airlines
Deal found 6/21$259
This American Airlines deal was found by Cheapflights users on 6/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:21 pm
RAP
-
ORD
Nonstop2h 39m
American Airlines
Mon 8/249:43 am
ORD
-
RAP
Nonstop2h 32m
American Airlines
Deal found 6/21$260
This CheapOair deal was found by Cheapflights users on 6/18. 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 7/318:08 pm
FSD
-
ORD
1 stop24h 44m
Frontier
Tue 8/49:57 pm
ORD
-
FSD
1 stop21h 26m
Frontier
Deal found 6/18$260
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/91:31 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Wed 9/165:00 am
ORD
-
RAP
1 stop5h 27m
United Airlines
Deal found 6/19$261
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Sun 7/197:35 am
FSD
-
ORD
Nonstop1h 56m
United Airlines
Sun 7/269:30 pm
ORD
-
FSD
Nonstop2h 01m
United Airlines
Deal found 6/19$263
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/37:11 am
FSD
-
ORD
Nonstop1h 59m
American Airlines
Wed 7/222:30 pm
ORD
-
FSD
Nonstop1h 54m
American Airlines
Deal found 6/19$264
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Mon 8/33:25 pm
RAP
-
ORD
Nonstop2h 34m
American Airlines
Mon 8/101:20 pm
ORD
-
RAP
Nonstop2h 30m
American Airlines
Deal found 6/19$269
This Delta deal was found by Cheapflights users on 6/19. 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 9/91:05 pm
FSD
-
MDW
1 stop5h 14m
Delta
Sat 9/129:59 am
MDW
-
FSD
1 stop5h 47m
Delta
Deal found 6/19$269

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 June 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$235
(CheapOair)

One-way from

$131
(CheapOair)

Popular in

July

Cheapest in

January

Average price

$329

Good round-trip deal

$379 or less

Good one-way deal

$269 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. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 22, 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

Wed 10/28

2:25 pm-7:34 pm

1 stop4h 09m

Chicago O'Hare Intl

Sat 10/31

12:15 pm-3:46 pm

1 stop4h 31m

$271

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 8/19

6:48 am-1:10 pm

1 stop5h 22m

Chicago Midway

Mon 8/24

9:59 am-1:48 pm

1 stop4h 49m

$280

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 7/3

10:56 am-5:02 pm

1 stop6h 06m

Chicago O'Hare Intl

Wed 7/8

6:30 am-12:49 pm

1 stop6h 19m

$284

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 8/6

7:35 am-9:31 am

Nonstop1h 56m

Chicago O'Hare Intl

Sun 8/9

9:30 pm-11:31 pm

Nonstop2h 01m

$298

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 7/2

1:35 pm-4:59 pm

Nonstop2h 24m

Chicago O'Hare Intl

Sun 7/5

8:45 am-10:24 am

Nonstop2h 39m

$309

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 7/4

6:00 am-9:34 am

Nonstop2h 34m

Chicago O'Hare Intl

Sat 7/4

10:54 am-3:52 pm

1 stop5h 58m

$313
Quickest round-trip

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 8/12

7:47 am-9:39 am

Nonstop1h 52m

Chicago O'Hare Intl

Sat 8/15

9:30 pm-11:22 pm

Nonstop1h 52m

$319

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 7/18

4:40 pm-10:49 pm

1 stop5h 09m

Chicago O'Hare Intl

Sun 7/19

6:00 am-11:30 am

1 stop6h 30m

$321

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 7/2

11:00 am-5:02 pm

1 stop5h 02m

Chicago O'Hare Intl

Sun 7/5

6:15 pm-10:37 pm

1 stop5h 22m

$329

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 9/4

1:26 pm-7:30 pm

1 stop6h 04m

Chicago O'Hare Intl

Mon 9/7

6:00 am-12:38 pm

1 stop6h 38m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/19

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, April is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $151). Flying from South Dakota to Chicago in June is currently the most expensive (average of $219). 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 June 22, 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 24% on airfare.

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 June 22, 2026.

The most flights from USSD to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

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

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

Booking 50 days in advance of your planned departure date is, on average, the best time to get cheap flights from South Dakota to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 May 16, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 and United Airlines fly from South Dakota to Chicago in about 4h 09m. The time it takes to get you to your destination can typically vary by up to 53m. 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 Envoy Air (85%), United Airlines (77%) and Copa Airlines (76%).

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

    On average you can expect to pay $683 for a flight from South Dakota to Chicago. The cheapest flight overall is $225 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, April is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $151). Flying from South Dakota to Chicago in June is currently the most expensive (average of $219). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for South Dakota to Chicago

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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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$337FlexibilityNo cancel feeOn-time69%

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