HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$116+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Jul 16 — Jul 231
Thu 7/16
Thu 7/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from South Dakota to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 16, 2026.

This American Airlines deal was found by Cheapflights users on 6/11. 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 9/412:06 pm
FSD
-
ORD
Nonstop1h 59m
American Airlines
Mon 9/710:40 pm
ORD
-
FSD
Nonstop1h 50m
American Airlines
Deal found 6/11$249
This United Airlines deal was found by Cheapflights users on 6/14. 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 10/97:50 am
FSD
-
ORD
Nonstop1h 52m
United Airlines
Mon 10/129:20 pm
ORD
-
FSD
Nonstop1h 51m
United Airlines
Deal found 6/14$257
This United Airlines deal was found by Cheapflights users on 6/13. 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 10/237:50 am
FSD
-
ORD
Nonstop1h 52m
United Airlines
Sun 10/257:45 pm
ORD
-
FSD
Nonstop1h 58m
United Airlines
Deal found 6/13$258
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/35:34 pm
FSD
-
ORD
1 stop6h 05m
American Airlines
Fri 8/73:00 pm
ORD
-
FSD
Nonstop1h 53m
American Airlines
Deal found 6/11$259
This American Airlines deal was found by Cheapflights users on 6/15. 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 8/2012:20 pm
RAP
-
ORD
Nonstop2h 29m
American Airlines
Tue 8/259:43 am
ORD
-
RAP
Nonstop2h 32m
American Airlines
Deal found 6/15$260
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/265:34 pm
FSD
-
ORD
1 stop7h 16m
American Airlines
Sun 8/210:30 pm
ORD
-
FSD
Nonstop1h 48m
American Airlines
Deal found 6/11$260
This American Airlines deal was found by Cheapflights users on 6/14. 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 8/14:55 pm
RAP
-
ORD
1 stop6h 55m
American Airlines
Tue 8/49:40 am
ORD
-
RAP
Nonstop2h 34m
American Airlines
Deal found 6/14$261
This United Airlines deal was found by Cheapflights users on 6/13. 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 7/316:28 pm
FSD
-
ORD
Nonstop1h 58m
United Airlines
Tue 8/49:30 pm
ORD
-
FSD
Nonstop2h 01m
United Airlines
Deal found 6/13$262
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/312:01 pm
FSD
-
ORD
Nonstop1h 58m
American Airlines
Wed 7/82:30 pm
ORD
-
FSD
Nonstop1h 54m
American Airlines
Deal found 6/15$264
This American Airlines deal was found by Cheapflights users on 6/15. 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 8/203:21 pm
RAP
-
ORD
Nonstop2h 39m
American Airlines
Mon 8/241:20 pm
ORD
-
RAP
Nonstop2h 30m
American Airlines
Deal found 6/15$269
This Delta deal was found by Cheapflights users on 6/11. 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 9/510:54 am
FSD
-
MDW
1 stop5h 03m
Delta
Tue 9/86:45 pm
MDW
-
FSD
1 stop4h 01m
Delta
Deal found 6/11$269
This Delta deal was found by Cheapflights users on 6/11. 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 9/510:54 am
FSD
-
ORD
1 stop6h 47m
Delta
Tue 9/85:20 pm
ORD
-
FSD
1 stop5h 26m
Delta
Deal found 6/11$269

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 June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$116
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$329

Good round-trip deal

$382 or less

Good one-way deal

$262 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.
Search Deals
From South Dakota to Chicago (CHI)
Search Deals
One-way flight from South Dakota to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from South Dakota to Chicago (CHI).
Search Deals
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 June 16, 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 - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 7/4

1:13 pm-5:54 pm

1 stop4h 41m

Chicago Midway

Tue 7/7

7:06 pm-11:06 pm

1 stop4h 00m

$269

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 9/5

10:54 am-3:57 pm

1 stop5h 03m

Chicago Midway

Tue 9/8

6:45 pm-10:46 pm

1 stop4h 01m

$269

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 7/3

5:12 am-8:35 am

1 stop3h 23m

Chicago O'Hare Intl

Wed 7/8

6:30 am-12:49 pm

1 stop6h 19m

$269

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 9/10

1:31 pm-4:55 pm

Nonstop2h 24m

Chicago O'Hare Intl

Wed 9/16

12:45 pm-5:53 pm

1 stop6h 08m

$270

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 8/20

1:31 pm-4:55 pm

Nonstop2h 24m

Chicago O'Hare Intl

Mon 8/24

5:00 am-9:28 am

1 stop5h 28m

$279

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 8/27

1:31 pm-4:55 pm

Nonstop2h 24m

Chicago O'Hare Intl

Sun 8/30

7:00 am-11:55 am

1 stop5h 55m

$279

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 10/3

1:05 pm-6:11 pm

1 stop5h 06m

Chicago Midway

Sun 10/4

1:47 pm-7:43 pm

1 stop5h 56m

$284

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 8/1

6:00 am-9:34 am

Nonstop2h 34m

Chicago O'Hare Intl

Tue 8/4

8:45 am-10:24 am

Nonstop2h 39m

$288

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Thu 7/23

1:35 pm-4:59 pm

Nonstop2h 24m

Chicago O'Hare Intl

Sat 7/25

6:00 am-11:30 am

1 stop6h 30m

$292

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 7/10

5:53 pm-12:44 am

1 stop5h 51m

Chicago O'Hare Intl

Mon 7/13

9:30 pm-11:16 pm

Nonstop2h 46m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, April is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $151). Flying from South Dakota to Chicago in June is currently the most expensive (average of $219). 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 June 16, 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 24% 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 June 16, 2026.

The most flights from USSD to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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

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

Booking 50 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. Monday evenings 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 Delta and United Airlines fly from South Dakota to Chicago in about 2h 24m. The time it takes to get you to your destination can typically vary by up to 2h 17m. The distance from South Dakota to Chicago is about 777 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 SkyWest Airlines (78%), United Airlines (75%) and Envoy Air (73%).

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

    On average you can expect to pay $701 for a flight from South Dakota to Chicago. The cheapest flight overall is $168 while the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl) is currently priced at $249.

  • 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, April is the cheapest month in which you can book a flight from South Dakota to Chicago (average of $151). Flying from South Dakota to Chicago in June is currently the most expensive (average of $219). 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
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for South Dakota to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Hobby to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Orlando to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Raleigh to O'Hare Intl flights
Miami to O'Hare Intl flights
Hobby to Midway flights
Dulles Intl to Midway flights
Atlanta to Midway flights
Fort Lauderdale to O'Hare Intl flights
San Diego to O'Hare Intl flights
Charlotte to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Santa Ana to O'Hare Intl flights
San Francisco to Midway flights
LaGuardia to St. Louis flights
Tampa to Midway flights
Minneapolis to O'Hare Intl flights
Minneapolis to Midway flights
Newark to St. Louis flights
San Jose to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Hartford to O'Hare Intl flights
Denver to Midway flights
Las Vegas to O'Hare Intl flights
George Bush Intcntl to Midway flights
Baltimore to Midway flights
Salt Lake City to O'Hare Intl flights
Reagan-National to Midway flights

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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$273FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$337FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.