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$105+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
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 August 11, 2025.

Round-trip from

$189
(American Airlines)

One-way from

$105
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$294

Good round-trip deal

$329 or less

Good one-way deal

$225 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. 10% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 11, 2025.

This American Airlines deal was found by Cheapflights users on 8/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:16 pmFSD - ORD
Nonstop1h 58mAmerican Airlines
Sun 11/94:49 pmORD - FSD
Nonstop1h 56mAmerican Airlines
Deal found 8/9$189
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/512:19 pmFSD - ORD
Nonstop1h 53mAmerican Airlines
Mon 9/810:07 pmORD - FSD
Nonstop1h 50mAmerican Airlines
Deal found 8/10$190
This American Airlines deal was found by Cheapflights users on 8/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amFSD - ORD
Nonstop1h 46mAmerican Airlines
Sat 8/303:30 pmORD - FSD
Nonstop2h 03mAmerican Airlines
Deal found 8/9$194
This American Airlines deal was found by Cheapflights users on 8/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:00 amFSD - ORD
Nonstop1h 46mAmerican Airlines
Mon 8/2510:20 pmORD - FSD
Nonstop2h 08mAmerican Airlines
Deal found 8/9$199
This American Airlines deal was found by Cheapflights users on 8/8. 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.
Thu 10/26:12 pmRAP - ORD
Nonstop2h 18mAmerican Airlines
Sun 10/511:08 amORD - RAP
Nonstop2h 34mAmerican Airlines
Deal found 8/8$209
This Delta deal was found by Cheapflights users on 8/9. 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.
Sat 8/3012:56 pmFSD - MDW
1 stop4h 41mDelta
Sat 9/67:17 pmMDW - FSD
1 stop4h 29mDelta
Deal found 8/9$209
This Delta deal was found by Cheapflights users on 8/10. 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 9/105:00 amFSD - ORD
1 stop3h 24mDelta
Sat 9/135:15 pmORD - FSD
1 stop5h 29mDelta
Deal found 8/10$209
This Priceline deal was found by Cheapflights users on 8/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:54 pmFSD - ORD
1 stop9h 05mFrontier
Mon 9/156:00 amORD - FSD
1 stop8h 09mFrontier
Deal found 8/9$212
This Delta deal was found by Cheapflights users on 8/9. 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.
Wed 9/245:00 amFSD - MDW
2 stops7h 28mDelta
Sat 9/277:15 pmMDW - FSD
1 stop3h 29mDelta
Deal found 8/9$214
This Delta deal was found by Cheapflights users on 8/9. 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.
Sat 8/3012:56 pmFSD - ORD
2 stops11h 00mDelta
Sun 8/316:10 amORD - FSD
1 stop4h 09mDelta
Deal found 8/9$215
This United Airlines deal was found by Cheapflights users on 8/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:59 pmRAP - ORD
1 stop5h 00mUnited Airlines
Tue 9/98:53 amORD - RAP
Nonstop2h 29mUnited Airlines
Deal found 8/9$219
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/186:03 pmFSD - ORD
Nonstop1h 46mAmerican Airlines
Mon 8/2510:20 pmORD - FSD
Nonstop2h 08mAmerican Airlines
Deal found 8/10$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 August 11, 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

Fri 11/7

7:16 pm-9:14 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 11/10

8:29 am-10:27 am

Nonstop1h 58m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 9/5

12:19 pm-2:12 pm

Nonstop1h 53m

Chicago O'Hare Intl

Mon 9/8

10:07 pm-11:57 pm

Nonstop1h 50m

$190

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 8/27

6:00 am-7:46 am

Nonstop1h 46m

Chicago O'Hare Intl

Sat 8/30

3:30 pm-5:33 pm

Nonstop2h 03m

$194

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 8/23

6:00 am-7:46 am

Nonstop1h 46m

Chicago O'Hare Intl

Mon 8/25

10:20 pm-12:28 am

Nonstop2h 08m

$199

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 9/24

5:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Sat 9/27

9:20 am-3:26 pm

1 stop6h 06m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 9/10

5:00 am-8:24 am

1 stop3h 24m

Chicago O'Hare Intl

Sat 9/13

8:52 am-12:11 pm

1 stop3h 19m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Mon 9/8

2:54 pm-11:59 pm

1 stop9h 05m

Chicago O'Hare Intl

Mon 9/15

6:00 am-2:09 pm

1 stop8h 09m

$212

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 8/21

6:03 pm-7:49 pm

Nonstop1h 46m

Chicago O'Hare Intl

Mon 9/8

10:07 pm-11:57 pm

Nonstop1h 50m

$214

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 8/30

12:56 pm-11:56 pm

2 stops11h 00m

Chicago O'Hare Intl

Sun 8/31

6:10 am-10:19 am

1 stop4h 09m

$215

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 8/21

2:08 pm-12:32 am

1 stop10h 24m

Chicago O'Hare Intl

Mon 9/8

6:00 am-2:09 pm

1 stop8h 09m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

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, 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 August 11, 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 August 11, 2025.

The most flights from USSD to CHI are scheduled on a Monday (18 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 11, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from South Dakota to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,920 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,221 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 (90%), Envoy Air (78%) and Air New Zealand (69%).

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

    On average you can expect to pay $1,500 for a flight from South Dakota to Chicago. The cheapest flight overall is $159 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
Valparaiso
Chesterton

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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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$172Average$195FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$249FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$193Average$321FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$311FlexibilityNo cancel feeOn-timeN/A

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