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$87+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
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 January 1, 2026.

This United Airlines deal was found by Cheapflights users on 12/30. 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 12/313:08 pmFSD - ORD
Nonstop2h 02mUnited Airlines
Sat 1/37:55 pmORD - FSD
Nonstop2h 01mUnited Airlines
Deal found 12/30$454
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/313:08 pmFSD - ORD
Nonstop2h 02mUnited Airlines
Thu 1/17:55 pmORD - FSD
Nonstop2h 01mUnited Airlines
Deal found 12/30$629
This Delta deal was found by Cheapflights users on 12/29. 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 12/315:00 amFSD - MDW
1 stop6h 06mDelta
Fri 1/25:59 pmMDW - FSD
1 stop5h 09mDelta
Deal found 12/29$659
This Delta deal was found by Cheapflights users on 12/29. 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 12/311:25 pmFSD - ORD
2 stops7h 11mDelta
Fri 1/26:30 pmORD - FSD
1 stop4h 38mDelta
Deal found 12/29$739
This Delta deal was found by Cheapflights users on 12/30. 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 12/311:25 pmFSD - MDW
1 stop3h 54mDelta
Thu 1/111:48 amMDW - FSD
1 stop3h 57mDelta
Deal found 12/30$864
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Tue 12/301:27 pmRAP - ORD
Nonstop2h 36mUnited Airlines
Tue 1/67:10 amORD - RAP
1 stop7h 02mUnited Airlines
Deal found 12/30$888

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 January 1, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$87
(Frontier)

Popular in

June

Cheapest in

January

Average price

$236

Good round-trip deal

$330 or less

Good one-way deal

$258 or less
Provider with most accurate pricing for Sioux Falls Joe Foss Field-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Sioux Falls Joe Foss Field-Chicago (CHI) flights.
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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).
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 January 2026
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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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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 January 1, 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 - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 4/3

2:06 pm-3:52 pm

Nonstop1h 46m

Chicago O'Hare Intl

Tue 4/7

5:20 pm-7:14 pm

Nonstop1h 54m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 2/7

11:22 am-1:15 pm

Nonstop1h 53m

Chicago O'Hare Intl

Mon 2/9

7:58 pm-9:50 pm

Nonstop1h 52m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 2/19

7:42 pm-9:30 pm

Nonstop1h 48m

Chicago O'Hare Intl

Sat 2/21

9:51 am-11:42 am

Nonstop1h 51m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 1/29

7:30 am-9:32 am

Nonstop2h 02m

Chicago O'Hare Intl

Sun 2/1

7:58 pm-9:50 pm

Nonstop1h 52m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 2/20

6:45 am-8:45 am

Nonstop2h 00m

Chicago O'Hare Intl

Sun 2/22

9:51 am-11:42 am

Nonstop1h 51m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 2/13

12:14 pm-2:02 pm

Nonstop1h 48m

Chicago O'Hare Intl

Sun 2/15

9:51 am-11:42 am

Nonstop1h 51m

$190

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 2/7

11:00 am-4:16 pm

1 stop5h 16m

Chicago Midway

Mon 2/9

7:16 pm-11:04 pm

1 stop3h 48m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 2/13

1:00 pm-6:40 pm

1 stop5h 40m

Chicago Midway

Sun 2/15

11:45 am-3:34 pm

1 stop3h 49m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 4/22

1:38 pm-6:45 pm

1 stop5h 07m

Chicago Midway

Sun 4/26

7:18 pm-11:02 pm

1 stop3h 44m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

1:00 pm-6:40 pm

1 stop5h 40m

Chicago Midway

Sat 2/21

11:45 am-3:34 pm

1 stop3h 49m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 44 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 January 1, 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 19% 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 December 27, 2025.

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. Wednesday 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 January 1, 2026.

The most flights from USSD to CHI are scheduled on a Monday (15 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).

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 American Airlines, United Airlines, and Delta fly from South Dakota to Chicago in about 1h 46m. The time it takes to get you to your destination can typically vary by up to 3h 30m. 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, Rapid City - Chicago O'Hare Intl or Sioux Falls Joe Foss Field - Chicago Midway 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 GoJet (79%), Copa Airlines (77%) and Air New Zealand (71%).

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

    On average you can expect to pay $815 for a flight from South Dakota to Chicago. The cheapest flight overall is $168 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, 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
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for South Dakota to Chicago

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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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$178Average$198FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$223FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$329FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$283FlexibilityNo cancel feeOn-timeN/A

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