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$94+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap 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 septiembre 17, 2025.

Round-trip from

$148
(Priceline)

One-way from

$94
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$334

Good round-trip deal

$295 or less

Good one-way deal

$192 or less
From South Dakota to Chicago (CHI)
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One-way flight from South Dakota to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from South Dakota to Chicago (CHI).
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Price to beat on a one-way flight from South Dakota to Chicago (CHI).
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Find 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 septiembre 17, 2025.

This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/312:32 pmFSD - ORD
1 stop9h 44mFrontier
dom. 11/25:00 amORD - FSD
1 stop7h 38mFrontier
Deal found 9/16$148
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/32:54 pmFSD - ORD
1 stop9h 05mFrontier
lun. 10/66:10 amORD - FSD
1 stop7h 59mFrontier
Deal found 9/15$158
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/72:32 pmFSD - ORD
1 stop9h 43mFrontier
lun. 11/106:00 amORD - FSD
1 stop7h 47mFrontier
Deal found 9/15$188
This American Airlines deal was found by Cheapflights users on 9/15. 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.
vie. 11/77:16 pmFSD - ORD
Nonstop1h 58mAmerican Airlines
dom. 11/98:29 amORD - FSD
Nonstop1h 58mAmerican Airlines
Deal found 9/15$189
This American Airlines deal was found by Cheapflights users on 9/17. 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.
sáb. 11/16:00 amFSD - ORD
Nonstop1h 52mAmerican Airlines
sáb. 11/88:29 amORD - FSD
Nonstop1h 58mAmerican Airlines
Deal found 9/17$191
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/107:28 pmFSD - ORD
1 stop5h 31mFrontier
dom. 10/126:50 amORD - FSD
1 stop6h 48mFrontier
Deal found 9/16$193
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:10 pmFSD - ORD
Nonstop1h 59mUnited Airlines
sáb. 10/48:45 amORD - FSD
Nonstop1h 52mUnited Airlines
Deal found 9/15$199
This United Airlines deal was found by Cheapflights users on 9/16. 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.
sáb. 10/181:44 pmRAP - ORD
Nonstop2h 21mUnited Airlines
dom. 10/198:45 amORD - RAP
Nonstop2h 28mUnited Airlines
Deal found 9/16$209
This Delta deal was found by Cheapflights users on 9/17. 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.
sáb. 11/15:20 amFSD - MDW
1 stop5h 10mDelta
sáb. 11/89:20 amMDW - FSD
1 stop3h 35mDelta
Deal found 9/17$209
This Delta deal was found by Cheapflights users on 9/16. 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.
vie. 10/315:20 amFSD - ORD
1 stop3h 43mDelta
sáb. 11/13:50 pmORD - FSD
1 stop3h 29mDelta
Deal found 9/16$209
This United Airlines deal was found by Cheapflights users on 9/16. 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.
vie. 10/103:12 pmFSD - ORD
Nonstop1h 58mUnited Airlines
mié. 10/158:30 pmORD - FSD
Nonstop1h 52mUnited Airlines
Deal found 9/16$217
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/1412:56 pmRAP - ORD
1 stop6h 29mUnited Airlines
mar. 10/218:45 amORD - RAP
Nonstop2h 28mUnited Airlines
Deal found 9/15$219

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 septiembre 17, 2025.
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 - ORD

FSDORD

Sioux Falls Joe Foss Field

vie. 11/7

2:32 pm-12:15 am

1 stop9h 43m

Chicago O'Hare Intl

lun. 11/10

6:00 am-1:47 pm

1 stop7h 47m

$188

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

sáb. 12/6

8:00 am-9:53 am

Nonstop1h 53m

Chicago O'Hare Intl

sáb. 12/13

8:04 pm-9:51 pm

Nonstop1h 47m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

mar. 9/30

6:10 pm-8:09 pm

Nonstop1h 59m

Chicago O'Hare Intl

sáb. 10/4

8:45 am-10:37 am

Nonstop1h 52m

$199

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

sáb. 10/4

8:00 am-9:51 am

Nonstop1h 51m

Chicago O'Hare Intl

dom. 10/5

8:30 pm-10:22 pm

Nonstop1h 52m

$199

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

sáb. 11/1

5:20 am-10:30 am

1 stop5h 10m

Chicago Midway

sáb. 11/8

9:20 am-12:55 pm

1 stop3h 35m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

mié. 3/4

5:15 am-8:54 am

1 stop3h 39m

Chicago Midway

sáb. 3/7

6:45 pm-10:58 pm

1 stop4h 13m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

sáb. 11/1

10:56 am-4:50 pm

1 stop5h 54m

Chicago O'Hare Intl

sáb. 11/8

8:57 am-12:55 pm

1 stop3h 58m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

vie. 10/31

5:20 am-9:03 am

1 stop3h 43m

Chicago O'Hare Intl

sáb. 11/1

3:50 pm-7:19 pm

1 stop3h 29m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

sáb. 2/28

10:58 am-8:38 pm

2 stops9h 40m

Chicago O'Hare Intl

mié. 3/4

6:00 am-12:35 pm

1 stop6h 35m

$214

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

mar. 10/14

12:56 pm-8:25 pm

1 stop6h 29m

Chicago O'Hare Intl

mar. 10/21

8:45 am-10:13 am

Nonstop2h 28m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 57 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, August is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $245). Flying from South Dakota to Chicago in March is currently the most expensive (average of $321). 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 septiembre 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from South Dakota to Chicago as you normally would.

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 septiembre 17, 2025.

The most flights from USSD to CHI are scheduled on a Monday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 Frontier, United Airlines, and Delta fly from South Dakota to Chicago in about 1h 53m. The time it takes to get you to your destination can typically vary by up to 7h 50m. The distance from South Dakota to Chicago is about 461 mi. This flight may include one or multiple stops.

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

    $94 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $129 and $186, respectively.

  • 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 Copa Airlines (86%), Qatar Airways (80%) and Air New Zealand (71%).

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

    On average you can expect to pay $1,614 for a flight from South Dakota to Chicago. The cheapest flight overall is $164 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $189.

  • 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, August is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $245). Flying from South Dakota to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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Top 4 airlines flying from South Dakota to Chicago

Discover the top 4 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$172Average$192FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$234FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$325FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$311FlexibilityNo cancel feeOn-timeN/A

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