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$61+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from South Dakota to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from South Dakota (USSD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$110
(Frontier)

One-way from

$61
(Frontier)

Popular in

April

Cheapest in

January

Average price

$218

Good round-trip deal

$190 or less

Good one-way deal

$269 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. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Frontier deal was found by Cheapflights users on 1/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:35 pmFSD - MDW
1 stop9h 42mFrontier
Wed 3/126:40 amMDW - FSD
1 stop7h 12mFrontier
Deal found 1/30$110
This Frontier deal was found by Cheapflights users on 1/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:35 pmFSD - ORD
1 stop10h 09mFrontier
Wed 3/126:45 amORD - FSD
1 stop7h 07mFrontier
Deal found 1/30$110
This United Airlines deal was found by Cheapflights users on 1/30. 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 3/56:38 pmFSD - ORD
Nonstop1h 47mUnited Airlines
Sat 3/88:20 pmORD - FSD
Nonstop1h 55mUnited Airlines
Deal found 1/30$189
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:45 pmRAP - ORD
Nonstop2h 18mUnited Airlines
Tue 5/132:35 pmORD - RAP
1 stop6h 51mUnited Airlines
Deal found 1/29$199
This Delta deal was found by Cheapflights users on 1/29. 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.
Thu 2/205:05 amFSD - MDW
1 stop4h 30mDelta
Mon 2/246:59 pmMDW - FSD
1 stop4h 08mDelta
Deal found 1/29$209
This Delta deal was found by Cheapflights users on 1/30. 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.
Thu 2/201:18 pmFSD - ORD
1 stop4h 11mDelta
Mon 2/247:10 pmORD - FSD
1 stop3h 57mDelta
Deal found 1/30$209
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:40 amFSD - ORD
Nonstop1h 50mAmerican Airlines
Sat 9/139:55 amORD - FSD
1 stop6h 59mAmerican Airlines
Deal found 1/30$229
This Delta deal was found by Cheapflights users on 1/29. 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.
Mon 4/214:25 pmRAP - ORD
1 stop4h 55mDelta
Tue 4/296:40 amORD - RAP
1 stop5h 19mDelta
Deal found 1/29$289
This Delta deal was found by Cheapflights users on 1/30. 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.
Thu 2/276:00 amRAP - MDW
1 stop5h 42mDelta
Thu 3/610:19 amMDW - RAP
1 stop6h 14mDelta
Deal found 1/30$289
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1911:38 amFSD - ORD
2 stops20h 57mMultiple Airlines
Tue 4/2210:19 amORD - FSD
2 stops26h 30mMultiple Airlines
Deal found 1/29$394
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/267:07 pmRAP - ORD
3 stops34h 00mMultiple Airlines
Wed 3/59:16 amORD - RAP
3 stops37h 03mMultiple Airlines
Deal found 1/29$449
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Tue 4/85:36 amRAP - ORD
1 stop8h 45mAmerican Airlines
Thu 4/108:35 pmORD - RAP
1 stop16h 21mAmerican Airlines
Deal found 1/29$527

Find flights from South Dakota to Chicago within your budget

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 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Mon 3/10

2:35 pm-12:17 am

1 stop9h 42m

Chicago Midway

Wed 3/12

6:40 am-1:52 pm

1 stop7h 12m

$110

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Mon 3/10

2:35 pm-12:44 am

1 stop10h 09m

Chicago O'Hare Intl

Wed 3/12

6:45 am-1:52 pm

1 stop7h 07m

$110

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Wed 3/5

6:38 pm-8:25 pm

Nonstop1h 47m

Chicago O'Hare Intl

Sat 3/8

8:20 pm-10:15 pm

Nonstop1h 55m

$189

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 5/9

12:45 pm-4:03 pm

Nonstop2h 18m

Chicago O'Hare Intl

Tue 5/13

2:35 pm-8:26 pm

1 stop6h 51m

$199

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 2/20

5:05 am-9:35 am

1 stop4h 30m

Chicago Midway

Mon 2/24

6:59 pm-11:07 pm

1 stop4h 08m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 2/20

1:18 pm-5:29 pm

1 stop4h 11m

Chicago O'Hare Intl

Mon 2/24

7:10 pm-11:07 pm

1 stop3h 57m

$209

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Mon 4/21

4:25 pm-10:20 pm

1 stop4h 55m

Chicago O'Hare Intl

Tue 4/29

6:40 am-10:59 am

1 stop5h 19m

$289

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Thu 2/27

6:00 am-12:42 pm

1 stop5h 42m

Chicago Midway

Thu 3/6

10:19 am-3:33 pm

1 stop6h 14m

$289

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 3/1

5:41 pm-8:23 am

1 stop14h 42m

Chicago O'Hare Intl

Sun 3/2

10:00 am-11:49 am

Nonstop1h 49m

$342

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 4/19

11:38 am-8:35 am

2 stops20h 57m

Chicago O'Hare Intl

Tue 4/22

10:19 am-12:49 pm

2 stops26h 30m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 23 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.

Travel insights for flights from South Dakota to Chicago

Get recent, data-driven insights about flights from South Dakota to Chicago including ideal travel times, pricing trends, and more.

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 $325). 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 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 January 30, 2025.

The most flights from USSD to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 January 30, 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
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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
8,454 reviews
Delta
8.0
Very good
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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
8,913 reviews
Delta
8.0
Very good
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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
790 reviews
Delta
8.0
Very good
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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
3,424 reviews
Delta
8.0
Very good
8,454 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

8.0

Crew

8.5

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?

    $61 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $198 and $214, 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 Republic Airways (89%), Air Wisconsin (89%) and Copa Airlines (89%).

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

    On average you can expect to pay $778 for a flight from South Dakota to Chicago. The cheapest flight overall is $193 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $209.

  • 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 $325). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$153Average$198FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$184Average$275FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$348FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$343FlexibilityNo cancel feeOn-timeN/A
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