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$99+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$169
(American Airlines)

One-way from

$99
(Frontier)

Popular in

March

Cheapest in

January

Average price

$311

Good round-trip deal

$178 or less

Good one-way deal

$204 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. 10% potential increase in price ($34 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 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 22, 2025.

This American Airlines deal was found by Cheapflights users on 4/22. 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 6/205:56 pmFSD - ORD
Nonstop1h 49mAmerican Airlines
Sun 6/223:38 pmORD - FSD
Nonstop1h 48mAmerican Airlines
Deal found 4/22$169
This Delta deal was found by Cheapflights users on 4/21. 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.
Fri 6/65:00 amFSD - ORD
1 stop3h 24mDelta
Sun 6/86:00 amORD - FSD
1 stop4h 15mDelta
Deal found 4/21$189
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 5/1512:45 pmRAP - ORD
Nonstop2h 18mUnited Airlines
Fri 6/67:45 pmORD - RAP
Nonstop2h 34mUnited Airlines
Deal found 4/21$209
This Frontier deal was found by Cheapflights users on 4/21. 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 4/21$220
This Delta deal was found by Cheapflights users on 4/21. 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 5/85:00 amFSD - MDW
1 stop3h 36mDelta
Sun 5/119:20 amMDW - FSD
1 stop6h 16mDelta
Deal found 4/21$229
This American Airlines deal was found by Cheapflights users on 4/21. 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 7/1212:47 pmRAP - ORD
Nonstop2h 18mAmerican Airlines
Tue 7/155:15 amORD - RAP
1 stop6h 34mAmerican Airlines
Deal found 4/21$232
This Delta deal was found by Cheapflights users on 4/21. 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 5/216:33 amRAP - ORD
1 stop6h 55mDelta
Sun 5/251:45 pmORD - RAP
2 stops9h 49mDelta
Deal found 4/21$234
This Delta deal was found by Cheapflights users on 4/22. 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 5/36:00 amRAP - MDW
1 stop7h 22mDelta
Wed 5/71:08 pmMDW - RAP
2 stops10h 26mDelta
Deal found 4/22$279
This CheapOair deal was found by Cheapflights users on 4/21. 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.
Fri 4/252:11 pmFSD - MDW
1 stop4h 55mFrontier
Sun 4/278:01 pmMDW - FSD
1 stop17h 20mFrontier
Deal found 4/21$291
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/158:00 amFSD - ORD
Nonstop1h 45mUnited Airlines
Wed 5/218:20 pmORD - FSD
Nonstop1h 52mUnited Airlines
Deal found 4/22$294
This Mytrip deal was found by Cheapflights users on 4/22. 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 5/154:35 pmORD - FSD
2 stops16h 33mMultiple Airlines
Deal found 4/22$301
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Sun 5/1810:12 pmRAP - ORD
1 stop11h 43mMultiple Airlines
Sat 5/244:35 pmORD - RAP
2 stops29h 39mMultiple Airlines
Deal found 4/21$358

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 22, 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 6/20

5:56 pm-7:45 pm

Nonstop1h 49m

Chicago O'Hare Intl

Sun 6/22

3:38 pm-5:26 pm

Nonstop1h 48m

$169

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 6/6

5:00 am-8:24 am

1 stop3h 24m

Chicago O'Hare Intl

Sun 6/8

6:00 am-10:15 am

1 stop4h 15m

$189

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 5/15

12:45 pm-4:03 pm

Nonstop2h 18m

Chicago O'Hare Intl

Fri 6/6

7:45 pm-9:19 pm

Nonstop2h 34m

$209

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

Thu 5/8

5:00 am-8:36 am

1 stop3h 36m

Chicago Midway

Sun 5/11

9:20 am-3:36 pm

1 stop6h 16m

$229

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 7/12

12:47 pm-4:05 pm

Nonstop2h 18m

Chicago O'Hare Intl

Tue 7/15

5:15 am-10:49 am

1 stop6h 34m

$232

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Wed 5/21

6:33 am-2:28 pm

1 stop6h 55m

Chicago O'Hare Intl

Sun 5/25

1:45 pm-10:34 pm

2 stops9h 49m

$234

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 5/3

6:00 am-2:22 pm

1 stop7h 22m

Chicago Midway

Wed 5/7

1:08 pm-10:34 pm

2 stops10h 26m

$279

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 8/8

7:30 pm-8:54 pm

1 stop25h 24m

Chicago Midway

Sun 8/17

2:44 pm-6:32 pm

1 stop27h 48m

$293

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 5/15

8:00 am-9:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Wed 5/21

8:20 pm-10:12 pm

Nonstop1h 52m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 26 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 22, 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 22, 2025.

The most flights from USSD to CHI are scheduled on a Tuesday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 22, 2025.
See what other customers who have flown with Delta, United Airlines and Allegiant Air 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
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
8,683 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
3,283 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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?

    $99 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 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 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 $910 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 $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
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 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$153Average$198FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$274FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$314FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$347FlexibilityNo cancel feeOn-timeN/A

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