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$103+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$169
(American Airlines)

One-way from

$103
(Trip.com)

Popular in

March

Cheapest in

January

Average price

$354

Good round-trip deal

$191 or less

Good one-way deal

$199 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. 13% potential increase in price ($46 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 April 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 April 30, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/175:58 pmFSD - ORD
Nonstop1h 46mAmerican Airlines
Thu 8/710:15 amORD - FSD
Nonstop2h 03mAmerican Airlines
Deal found 4/29$169
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 8/266:00 amFSD - MDW
2 stops6h 30mDelta
Thu 9/46:45 pmMDW - FSD
1 stop4h 02mDelta
Deal found 4/29$194
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 8/266:00 amFSD - ORD
2 stops6h 38mDelta
Thu 9/46:00 amORD - FSD
1 stop3h 52mDelta
Deal found 4/29$194
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/712:47 pmRAP - ORD
Nonstop2h 18mAmerican Airlines
Mon 9/1510:09 amORD - RAP
Nonstop2h 21mAmerican Airlines
Deal found 4/29$209
This United Airlines deal was found by Cheapflights users on 4/28. 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 6/71:38 pmRAP - ORD
Nonstop2h 22mUnited Airlines
Tue 6/105:02 amORD - RAP
1 stop5h 02mUnited Airlines
Deal found 4/28$219
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:58 pmFSD - ORD
1 stop8h 01mFrontier
Sun 6/86:00 amORD - FSD
1 stop8h 58mFrontier
Deal found 4/29$220
This CheapOair deal was found by Cheapflights users on 4/28. 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 5/122:08 pmFSD - MDW
1 stop5h 00mFrontier
Thu 5/158:03 pmMDW - FSD
1 stop17h 15mFrontier
Deal found 4/28$221
This Delta deal was found by Cheapflights users on 4/28. 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 8/216:20 amRAP - MDW
1 stop5h 42mDelta
Tue 8/266:45 pmMDW - RAP
1 stop4h 11mDelta
Deal found 4/28$229
This Delta deal was found by Cheapflights users on 4/28. 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 8/212:20 pmRAP - ORD
1 stop4h 23mDelta
Tue 8/261:35 pmORD - RAP
2 stops9h 21mDelta
Deal found 4/28$234
This United Airlines deal was found by Cheapflights users on 4/28. 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 10/106:11 pmFSD - ORD
Nonstop1h 59mUnited Airlines
Mon 10/138:15 pmORD - FSD
Nonstop1h 52mUnited Airlines
Deal found 4/28$234
This Mytrip deal was found by Cheapflights users on 4/28. 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 5/1210:00 amFSD - ORD
1 stop6h 25mMultiple Airlines
Thu 5/159:55 amORD - FSD
2 stops23h 13mMultiple Airlines
Deal found 4/28$301

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 April 30, 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 7/17

5:58 pm-7:44 pm

Nonstop1h 46m

Chicago O'Hare Intl

Thu 8/7

10:15 am-12:18 pm

Nonstop2h 03m

$169

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Tue 8/26

6:00 am-12:30 pm

2 stops6h 30m

Chicago Midway

Thu 9/4

6:45 pm-10:47 pm

1 stop4h 02m

$194

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Tue 8/26

6:00 am-12:38 pm

2 stops6h 38m

Chicago O'Hare Intl

Thu 9/4

6:00 am-9:52 am

1 stop3h 52m

$194

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sun 9/7

12:47 pm-4:05 pm

Nonstop2h 18m

Chicago O'Hare Intl

Mon 9/15

10:09 am-11:30 am

Nonstop2h 21m

$209

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 6/7

1:38 pm-5:00 pm

Nonstop2h 22m

Chicago O'Hare Intl

Tue 6/10

5:02 am-9:04 am

1 stop5h 02m

$219

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 6/6

3:58 pm-11:59 pm

1 stop8h 01m

Chicago O'Hare Intl

Sun 6/8

6:00 am-2:58 pm

1 stop8h 58m

$220

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Mon 5/12

2:08 pm-7:08 pm

1 stop5h 00m

Chicago Midway

Thu 5/15

8:03 pm-1:18 pm

1 stop17h 15m

$221

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Thu 8/21

6:20 am-1:02 pm

1 stop5h 42m

Chicago Midway

Tue 8/26

6:45 pm-9:56 pm

1 stop4h 11m

$229

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 10/10

6:11 pm-8:10 pm

Nonstop1h 59m

Chicago O'Hare Intl

Mon 10/13

8:15 pm-10:07 pm

Nonstop1h 52m

$234

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 8/21

2:20 pm-7:43 pm

1 stop4h 23m

Chicago O'Hare Intl

Tue 8/26

1:35 pm-9:56 pm

2 stops9h 21m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 22 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 April 30, 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 April 30, 2025.

The most flights from USSD to CHI are scheduled on a Tuesday (18 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 30, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from South Dakota to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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?

    $109 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $142 and $152, 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, Rapid City - Chicago O'Hare Intl or Rapid City - 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 Copa Airlines (84%), Air Wisconsin (80%) and Alaska Airlines (71%).

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

    On average you can expect to pay $628 for a flight from South Dakota to Chicago. The cheapest flight overall is $129 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $214.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$153Average$196FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$275FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$310FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$306FlexibilityNo cancel feeOn-timeN/A

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