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$88+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$174
(Priceline)

One-way from

$88
(Priceline)

Popular in

March

Cheapest in

January

Average price

$284

Good round-trip deal

$164 or less

Good one-way deal

$207 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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/3. 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.
Thu 7/102:57 pmFSD - ORD
1 stop9h 13mFrontier
Thu 7/175:40 amORD - FSD
1 stop8h 22mFrontier
Deal found 7/3$174
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/156:03 pmFSD - ORD
Nonstop1h 46mAmerican Airlines
Mon 8/1810:20 pmORD - FSD
Nonstop2h 08mAmerican Airlines
Deal found 7/3$189
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/166:26 pmFSD - ORD
Nonstop1h 50mUnited Airlines
Sun 7/208:08 pmORD - FSD
Nonstop1h 52mUnited Airlines
Deal found 7/1$199
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 9/76:12 pmRAP - ORD
Nonstop2h 18mAmerican Airlines
Mon 9/154:17 pmORD - RAP
Nonstop2h 25mAmerican Airlines
Deal found 7/2$200
This Delta deal was found by Cheapflights users on 7/3. 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 8/215:00 amFSD - MDW
1 stop3h 51mDelta
Sun 8/249:15 amMDW - FSD
1 stop4h 35mDelta
Deal found 7/3$209
This Delta deal was found by Cheapflights users on 7/3. 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 8/215:00 amFSD - ORD
1 stop3h 24mDelta
Sun 8/246:10 amORD - FSD
1 stop6h 06mDelta
Deal found 7/3$209
This United Airlines deal was found by Cheapflights users on 7/1. 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 9/511:18 amRAP - ORD
1 stop6h 08mUnited Airlines
Sun 9/75:00 amORD - RAP
1 stop5h 06mUnited Airlines
Deal found 7/1$211
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:11 pmFSD - ORD
2 stops23h 28mMultiple Airlines
Wed 10/88:00 amORD - FSD
2 stops26h 51mMultiple Airlines
Deal found 7/3$243
This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/97:48 pmFSD - MDW
1 stop25h 06mFrontier
Sat 7/122:44 pmMDW - FSD
1 stop23h 18mFrontier
Deal found 7/1$271
This Delta deal was found by Cheapflights users on 7/1. 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 8/146:26 amRAP - MDW
1 stop5h 37mDelta
Mon 8/187:17 pmMDW - RAP
1 stop4h 15mDelta
Deal found 7/1$314
This Delta deal was found by Cheapflights users on 7/2. 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 8/22:25 pmRAP - ORD
1 stop6h 09mDelta
Sun 8/32:00 pmORD - RAP
2 stops9h 31mDelta
Deal found 7/2$319
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/179:59 pmRAP - ORD
1 stop7h 04mMultiple Airlines
Sun 7/207:08 amORD - RAP
1 stop14h 51mMultiple Airlines
Deal found 7/2$323

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 July 3, 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

Thu 7/10

2:57 pm-12:10 am

1 stop9h 13m

Chicago O'Hare Intl

Thu 7/17

5:40 am-2:02 pm

1 stop8h 22m

$174

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 8/15

6:03 pm-7:49 pm

Nonstop1h 46m

Chicago O'Hare Intl

Mon 8/18

10:20 pm-12:28 am

Nonstop2h 08m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 7/16

6:26 pm-8:16 pm

Nonstop1h 50m

Chicago O'Hare Intl

Sun 7/20

8:08 pm-10:00 pm

Nonstop1h 52m

$199

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sun 9/7

6:12 pm-9:30 pm

Nonstop2h 18m

Chicago O'Hare Intl

Mon 9/15

4:17 pm-5:42 pm

Nonstop2h 25m

$200

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 8/21

5:00 am-8:51 am

1 stop3h 51m

Chicago Midway

Sun 8/24

9:15 am-1:50 pm

1 stop4h 35m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 8/16

10:59 am-3:02 pm

1 stop4h 03m

Chicago O'Hare Intl

Mon 8/18

8:20 pm-11:46 pm

1 stop3h 26m

$209

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 9/5

11:18 am-6:26 pm

1 stop6h 08m

Chicago O'Hare Intl

Sun 9/7

5:00 am-9:06 am

1 stop5h 06m

$211

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 8/1

11:57 am-6:03 am

1 stop18h 06m

Chicago O'Hare Intl

Fri 8/8

6:40 am-8:49 pm

1 stop14h 09m

$261

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 7/9

7:48 pm-8:54 pm

1 stop25h 06m

Chicago Midway

Sat 7/12

2:44 pm-2:02 pm

1 stop23h 18m

$271

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Thu 8/14

6:26 am-1:03 pm

1 stop5h 37m

Chicago Midway

Mon 8/18

7:17 pm-10:32 pm

1 stop4h 15m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 28 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 July 3, 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 July 3, 2025.

The most flights from USSD to CHI are scheduled on a Thursday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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

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 July 3, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and Allegiant Air 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
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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!
Allegiant Air
7.3
Good
708 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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
5.9
Fair
3,286 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

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 cheapest airlines to fly from South Dakota to Chicago one-way?

    $88 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 American Airlines, with prices starting from $214 and $224, 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 Piedmont Airlines (100%), Copa Airlines (94%) and Envoy Air (80%).

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

    On average you can expect to pay $1,941 for a flight from South Dakota to Chicago. The cheapest flight overall is $209 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 South Dakota?

Book flights to South Dakota if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$169Average$198FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$268FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$314FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$311FlexibilityNo cancel feeOn-timeN/A

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