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$101+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Sep 9 — Sep 161
Wed 9/9
Wed 9/16
1 adult, Economy
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Cheap 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 10, 2026.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:52 pm -
1 stop27h 31m
Mon 9/146:30 am -
1 stop13h 37m
Deal found 8/8$190
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/53:06 pm -
Nonstop1h 59m
Tue 9/89:20 pm -
Nonstop1h 52m
Deal found 8/5$236
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/2712:06 pm -
Nonstop1h 59m
Sun 8/3010:35 pm -
Nonstop1h 50m
Deal found 8/5$237
This CheapOair deal was found by Cheapflights users on 8/7. 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 11/68:48 pm -
1 stop13h 13m
Sun 11/810:40 pm -
1 stop21h 13m
Deal found 8/7$250
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/117:47 am -
Nonstop1h 52m
Sun 9/139:20 pm -
Nonstop1h 52m
Deal found 8/5$259
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/46:39 pm -
Nonstop1h 59m
Mon 9/79:30 pm -
Nonstop1h 52m
Deal found 8/5$266
This American Airlines deal was found by Cheapflights users on 8/7. 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 9/116:41 pm -
Nonstop2h 18m
Sun 9/136:00 am -
1 stop6h 16m
Deal found 8/7$269
This American Airlines deal was found by Cheapflights users on 8/7. 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 8/226:24 am -
Nonstop2h 06m
Sat 8/2910:40 pm -
Nonstop1h 50m
Deal found 8/7$274
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/246:07 pm -
Nonstop2h 38m
Mon 9/289:40 am -
Nonstop2h 35m
Deal found 8/6$279
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 9/1210:40 am -
1 stop5h 20m
Mon 9/147:13 pm -
1 stop3h 38m
Deal found 8/9$279
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.
Wed 9/21:31 pm -
Nonstop2h 24m
Wed 9/95:00 am -
1 stop5h 27m
Deal found 8/9$280
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:48 pm -
1 stop13h 13m
Mon 11/911:06 am -
1 stop8h 47m
Deal found 8/9$280

Find 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 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$190
(CheapOair)

One-way from

$101
(CheapOair)

Popular in

November

Cheapest in

January

Average price

$249

Good round-trip deal

$341 or less

Good one-way deal

$308 or less
Provider with most accurate pricing for Sioux Falls Joe Foss Field-Chicago (CHI) flight deals.
Search Deals
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)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
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).
Search Deals

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 10, 2026.
Use the filters below to find and compare flights from South Dakota to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl

FSDORD

Sioux Falls Joe Foss Field

Sat 9/5

3:06 pm-5:05 pm

Nonstop1h 59m

Chicago O'Hare Intl

Tue 9/8

9:20 pm-11:12 pm

Nonstop1h 52m

$236

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl

FSDORD

Sioux Falls Joe Foss Field

Sat 11/7

7:00 am-9:10 am

Nonstop2h 10m

Chicago O'Hare Intl

Mon 11/9

10:48 pm-12:39 am

Nonstop1h 51m

$259
Quickest round-trip

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl

FSDORD

Sioux Falls Joe Foss Field

Thu 8/27

6:39 pm-8:38 pm

Nonstop1h 59m

Chicago O'Hare Intl

Wed 9/2

8:40 am-10:29 am

Nonstop1h 49m

$274

Rapid CityChicago

RAP Rapid City - ORD Chicago O'Hare Intl

RAPORD

Rapid City

Thu 9/24

6:07 pm-9:45 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 9/28

6:00 am-12:17 pm

1 stop7h 17m

$289

Rapid CityChicago

RAP Rapid City - MDW Chicago Midway

RAPMDW

Rapid City

Sat 1/2

11:30 am-4:50 pm

1 stop4h 20m

Chicago Midway

Sun 1/10

12:30 pm-3:46 pm

1 stop4h 16m

$290

Rapid CityChicago

RAP Rapid City - ORD Chicago O'Hare Intl

RAPORD

Rapid City

Wed 9/2

5:58 pm-11:59 pm

1 stop5h 01m

Chicago O'Hare Intl

Wed 9/9

5:00 am-9:27 am

1 stop5h 27m

$290

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - ORD Chicago O'Hare Intl

FSDORD

Sioux Falls Joe Foss Field

Thu 8/27

8:22 am-11:37 am

1 stop3h 15m

Chicago O'Hare Intl

Wed 9/2

6:00 am-12:38 pm

1 stop6h 38m

$294

Rapid CityChicago

RAP Rapid City - ORD Chicago O'Hare Intl

RAPORD

Rapid City

Thu 11/12

2:23 pm-9:34 pm

1 stop6h 11m

Chicago O'Hare Intl

Sun 11/15

6:30 am-10:49 am

1 stop5h 19m

$299

Rapid CityChicago

RAP Rapid City - ORD Chicago O'Hare Intl

RAPORD

Rapid City

Thu 8/20

12:30 pm-6:32 pm

1 stop5h 02m

Chicago O'Hare Intl

Sun 8/23

5:00 am-9:28 am

1 stop5h 28m

$339

Rapid CityChicago

RAP Rapid City - ORD Chicago O'Hare Intl

RAPORD

Rapid City

Fri 10/30

5:50 pm-11:59 pm

1 stop5h 09m

Chicago O'Hare Intl

Sun 11/1

8:40 am-10:31 am

Nonstop2h 51m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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, November is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $246). Flying from South Dakota to Chicago in September is currently the most expensive (average of $359). 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 10, 2026.

One of the essential ways to save on airfare from South Dakota to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 26% on airfare.

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 10, 2026.

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 (9 on average).

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

Airfare is below average for this route at the moment.
South Dakota to Chicago flights typically cost between $249 and $319 in September.
The cheapest round-trip price found within the last 5 days was $190 on Frontier (Sep 11-Sep 14).

How far ahead should I book a flight from South Dakota to Chicago?

Booking 45 days in advance of your planned departure date is, on average, the best time to get cheap flights from South Dakota to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from South Dakota to Chicago?

Use this chart to determine the cheapest time to fly round-trip from South Dakota to Chicago. Price data was last updated on May 16, 2026.

Travelers seeking maximum savings on their South Dakota to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from South Dakota to Chicago?

    Airlines like United Airlines, American Airlines, and Delta fly from South Dakota to Chicago in about 1h 59m. The time it takes to get you to your destination can typically vary by up to 2h 21m. The distance from South Dakota to Chicago is about 461 mi. This flight may include one or multiple stops.

  • 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%), Air New Zealand (80%) and United Airlines (71%).

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

    On average you can expect to pay $575 for a flight from South Dakota to Chicago. The cheapest flight overall is $243 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $259.

  • 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, November is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $246). Flying from South Dakota to Chicago in September is currently the most expensive (average of $359). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for South Dakota to Chicago

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Top 2 airlines flying from South Dakota to Chicago

Discover the top 2 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 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$285FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$327FlexibilityNo cancel feeOn-time69%

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