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$98+ Cheap flights from Sioux Falls (FSD) 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
FSD — CHI
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheapflights Tip: The best prices from Sioux Falls Joe Foss Field to Chicago are usually found in September or January, booked 86 days in advance, depart on a Saturday or Friday and return on a Wednesday

Cheap flight deals from Sioux Falls to Chicago

Cheapest flights from Sioux Falls to Chicago
Explore the most affordable flight options available from Sioux Falls to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.

This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/151:44 pm
FSD
-
MDW
1 stop4h 52m
Delta
Sat 4/187:16 pm
MDW
-
FSD
1 stop3h 46m
Delta
Deal found 3/9$197
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 6/308:15 am
FSD
-
ORD
1 stop6h 43m
Delta
Fri 7/35:20 pm
ORD
-
FSD
1 stop5h 26m
Delta
Deal found 3/9$197
This Delta deal was found by Cheapflights users on 3/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:20 pm
FSD
-
ORD
2 stops7h 04m
Delta
Mon 10/265:20 pm
ORD
-
FSD
1 stop5h 31m
Delta
Deal found 3/8$202
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:53 pm
FSD
-
ORD
Nonstop1h 57m
United Airlines
Sun 4/58:45 am
ORD
-
FSD
Nonstop1h 57m
United Airlines
Deal found 3/6$209
This American Airlines deal was found by Cheapflights users on 3/7. 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.
Tue 9/2212:30 pm
FSD
-
ORD
Nonstop1h 50m
American Airlines
Mon 9/2810:00 pm
ORD
-
FSD
Nonstop1h 51m
American Airlines
Deal found 3/7$212
This Delta deal was found by Cheapflights users on 3/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:00 am
FSD
-
MDW
1 stop3h 50m
Delta
Tue 4/147:16 pm
MDW
-
FSD
1 stop3h 46m
Delta
Deal found 3/8$213
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 4/75:00 am
FSD
-
ORD
1 stop3h 40m
Delta
Tue 4/147:09 pm
ORD
-
FSD
1 stop3h 53m
Delta
Deal found 3/9$213
This Delta deal was found by Cheapflights users on 3/9. 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 4/49:50 am
FSD
-
ORD
1 stop5h 26m
Delta
Tue 4/76:15 am
ORD
-
FSD
1 stop4h 06m
Delta
Deal found 3/9$217
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:19 am
FSD
-
MDW
2 stops10h 14m
Delta
Sun 5/109:23 am
MDW
-
FSD
1 stop3h 26m
Delta
Deal found 3/6$218
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:19 am
FSD
-
ORD
2 stops9h 46m
Delta
Sun 5/108:42 am
ORD
-
FSD
1 stop4h 07m
Delta
Deal found 3/7$218
This United Airlines deal was found by Cheapflights users on 3/5. 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 7/107:40 am
FSD
-
ORD
Nonstop1h 56m
United Airlines
Sat 7/118:09 pm
ORD
-
FSD
Nonstop1h 58m
United Airlines
Deal found 3/5$219
This United Airlines deal was found by Cheapflights users on 3/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2711:21 am
FSD
-
ORD
Nonstop1h 54m
United Airlines
Sun 3/293:45 pm
ORD
-
FSD
Nonstop1h 59m
United Airlines
Deal found 3/7$224

Find flight deals from Sioux Falls to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Sioux Falls (FSD) 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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$197
(Delta)

One-way from

$98
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$335

Good round-trip deal

$370 or less

Good one-way deal

$339 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 Sioux Falls Joe Foss Field to Chicago (CHI)
Search Deals
One-way flight from Sioux Falls Joe Foss Field 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. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Sioux Falls Joe Foss Field to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Sioux Falls Joe Foss Field to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sioux Falls 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 March 10, 2026.
Use the filters below to find and compare flights from Sioux Falls 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

Thu 5/7

8:19 am-1:19 pm

1 stop5h 00m

Chicago Midway

Sun 5/10

7:13 pm-11:11 pm

1 stop3h 58m

$197

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 5/8

8:19 am-11:47 am

1 stop3h 28m

Chicago O'Hare Intl

Sun 5/10

2:00 pm-11:11 pm

2 stops9h 11m

$202

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 4/4

9:50 am-3:16 pm

1 stop5h 26m

Chicago O'Hare Intl

Tue 4/7

6:15 am-10:21 am

1 stop4h 06m

$217

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 4/30

5:00 am-8:38 am

1 stop3h 38m

Chicago O'Hare Intl

Sun 5/3

6:25 am-10:12 am

1 stop3h 47m

$257

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Tue 4/21

1:44 pm-7:52 pm

1 stop6h 08m

Chicago O'Hare Intl

Tue 4/28

6:25 am-10:12 am

1 stop3h 47m

$257

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Tue 4/21

5:00 am-12:43 pm

2 stops7h 43m

Chicago Midway

Tue 4/28

7:16 pm-11:02 pm

1 stop3h 46m

$262
Quickest round-trip

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Tue 4/7

7:39 am-9:21 am

Nonstop1h 42m

Chicago O'Hare Intl

Sat 4/11

3:45 pm-5:44 pm

Nonstop1h 59m

$269

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 5/22

5:00 am-6:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 5/24

7:40 pm-9:38 pm

Nonstop1h 58m

$273

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 7/3

8:15 am-2:58 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 7/8

6:00 am-12:28 pm

1 stop6h 28m

$289

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Tue 8/18

1:01 pm-2:55 pm

Nonstop1h 54m

Chicago O'Hare Intl

Thu 8/20

8:00 pm-9:52 pm

Nonstop1h 52m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 36 resultsSorted by cheapest first
1
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3
4

Compare providers for flights from Sioux Falls to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sioux Falls to Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Sioux Falls-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sioux Falls-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sioux Falls-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sioux Falls-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sioux Falls-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Sioux Falls to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sioux Falls 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 Sioux Falls to Chicago

How far ahead should I book a flight from Sioux Falls to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Sioux Falls to Chicago. Price data was last updated on March 6, 2026.

The best time to book flights from Sioux Falls to Chicago is 39 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Sioux Falls to Chicago?

Currently, April is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $183). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $221). 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 FSD to CHI?

Find hourly flight availability from Sioux Falls 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 March 10, 2026.

A simple way to save on the total cost of your ticket is to fly from Sioux Falls to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Sioux Falls to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Sioux Falls to Chicago. Price data was last updated on February 21, 2026.

Travelers seeking maximum savings on their Sioux Falls to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Sioux Falls to Chicago

Explore weekly flight availability from Sioux Falls 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 March 10, 2026.

The most flights from FSD to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

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 March 10, 2026.
Read through reviews of airlines operating flights from Sioux Falls to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,409 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,409 reviews
United Airlines
7.4
Good
9,409 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,413 reviews
United Airlines
7.4
Good
9,409 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Sioux Falls to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Sioux Falls to Chicago?

    For a flight from Sioux Falls to Chicago, you will be flying from Joe Foss Field. Sioux Falls Joe Foss Field (FSD) is just 2.6 mi from the center of the city. Joe Foss Field is the only Sioux Falls airport and it handles 17 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Sioux Falls Joe Foss Field on a regular basis.

  • How long is the flight from Sioux Falls to Chicago?

    For as low as $269, Delta can have you in Chicago from Sioux Falls in 1h 42m. Airlines will cover a distance of 461 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Sioux Falls to Chicago round-trip?

    Cheapflights users have booked flights from Sioux Falls to Chicago round-trip from $189. Another airline that can offer you cheap pricing is United Airlines. These flights start at 34% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Sioux Falls to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Sioux Falls to Chicago on time: Envoy Air (85%), Qatar Airways (84%), American Airlines (78%).

  • What are the cheapest flights from Sioux Falls to Chicago?

    While on average a flight from Sioux Falls to Chicago is generally $934, our data shows the cheapest flight currently is $266. When looking at the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl), you can expect to pay $209 for that flight.

  • Can I find deals for flights from Sioux Falls to Chicago that include hotel bookings?

    Yes. In addition to deals on Sioux Falls to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sioux Falls to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sioux Falls to Chicago.

  • Can I find deals for business class flights from Sioux Falls to Chicago?

    Yes. Cheapflights offers flight deals from Sioux Falls 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 Sioux Falls to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $183). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $221). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Sioux Falls to Chicago

Discover the top 2 airlines that operate flights from Sioux Falls 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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$221FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$311FlexibilityNo cancel feeOn-time69%

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