Chicago

$131+ Cheap flights from Sioux Falls (FSD) to Chicago (CHI)

FSD — CHI
Oct 9 — Oct 161
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Cheapflights Tip: The best prices from Sioux Falls Joe Foss Field to Chicago are usually found in January or August, booked 29 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap flight deals from Sioux Falls to Chicago

Cheapest flights from Sioux Falls to Chicago

Fri 10/97:39 pm -
Nonstop2h 01m
Mon 10/1210:48 pm -
Nonstop1h 53m
Deal found 9/4$279
Sat 10/247:39 pm -
Nonstop2h 01m
Sat 10/319:45 am -
Nonstop1h 54m
Deal found 9/9$280
Wed 10/1412:53 pm -
1 stop7h 45m
Sat 10/1710:48 pm -
Nonstop1h 53m
Deal found 9/5$289
Fri 9/256:41 pm -
Nonstop2h 18m
Sun 9/2710:39 pm -
Nonstop1h 50m
Deal found 9/5$294
Fri 10/235:54 pm -
1 stop6h 05m
Fri 10/305:00 am -
1 stop7h 13m
Deal found 9/8$298
Fri 10/28:52 pm -
1 stop27h 31m
Mon 10/56:30 am -
1 stop13h 37m
Deal found 9/7$300
Sat 9/196:41 pm -
Nonstop2h 18m
Mon 9/2110:39 pm -
Nonstop1h 50m
Deal found 9/5$309
Fri 9/118:52 pm -
1 stop27h 31m
Mon 9/146:30 am -
1 stop13h 37m
Deal found 9/6$315
Fri 12/411:01 am -
1 stop5h 49m
Mon 12/712:39 pm -
1 stop6h 36m
Deal found 9/7$319
Tue 10/135:10 am -
1 stop3h 34m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6$334
Fri 10/1611:00 am -
1 stop5h 47m
Sat 10/1710:12 am -
1 stop5h 48m
Deal found 9/6$349
Sat 12/511:01 am -
1 stop5h 49m
Wed 12/912:39 pm -
1 stop3h 41m
Deal found 9/5$384

Find flight deals from Sioux Falls to Chicago

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(American Airlines)

One-way from

$131
(CheapOair)

Popular in

November

Cheapest in

January

Average price

$313

Good round-trip deal

$374 or less

Good one-way deal

$353 or less
Provider with most accurate pricing for Sioux Falls Joe Foss Field-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Sioux Falls Joe Foss Field-Chicago (CHI) flights.
From Sioux Falls Joe Foss Field to Chicago (CHI)
One-way flight from Sioux Falls Joe Foss Field to Chicago (CHI)
Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in September 2026
Price to beat on a round-trip flight from Sioux Falls Joe Foss Field to Chicago (CHI).
Price to beat on a one-way flight from Sioux Falls Joe Foss Field to Chicago (CHI).

Cheapflights Fare Finder

 
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 Sioux Falls Joe Foss Field - MDW Chicago Midway

FSDMDW

Sioux Falls Joe Foss Field

Fri 10/2

8:52 pm-5:51 pm

2 stops20h 59m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$214

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Sat 10/10

11:00 am-9:27 pm

1 stop10h 27m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$237

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Sun 12/6

3:14 pm-5:14 pm

Nonstop2h 00m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$269
Quickest round-trip

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Fri 12/11

7:40 am-9:36 am

Nonstop1h 56m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$269

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Sat 10/3

5:04 pm-10:46 pm

1 stop5h 42m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$269

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - MDW Chicago Midway

FSDMDW

Sioux Falls Joe Foss Field

Sun 10/11

5:10 am-8:44 am

1 stop3h 34m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$279

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - MDW Chicago Midway

FSDMDW

Sioux Falls Joe Foss Field

Thu 10/8

8:30 am-11:47 am

1 stop3h 17m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$279

Sioux FallsChicago

FSD Sioux Falls Joe Foss Field - MDW Chicago Midway

FSDMDW

Sioux Falls Joe Foss Field

Wed 11/4

11:00 am-4:47 pm

1 stop5h 47m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$279

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Fri 12/4

5:02 pm-9:35 pm

1 stop4h 33m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$279

Sioux FallsChicago

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

FSDORD

Sioux Falls Joe Foss Field

Sun 11/8

5:10 am-11:40 am

1 stop6h 30m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/7

Showing 1-10 of 41 resultsSorted by cheapest first
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Compare providers for flights from Sioux Falls to Chicago

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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*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

Cheapflights Insights

Everything you need to know about your flight from Sioux Falls to Chicago

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

Currently, November is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $236). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $364). 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?

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 26% on your trip compared to booking a flight at noon.

Weekly flight availability from Sioux Falls to Chicago

The most flights from FSD to CHI are scheduled on a Monday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Sioux Falls to Chicago?

Airfare is typical for this route at the moment.
Sioux Falls to Chicago flights typically cost between $249 and $358 in October.
The cheapest round-trip price found within the last 5 days was $279 on American Airlines (Oct 9-Oct 12).

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

The best time to book flights from Sioux Falls to Chicago is 45 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 day to fly from Sioux Falls to Chicago?

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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Sioux Falls to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Overall

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
8.0
Excellent

Jorge,Aug 2026

TPA - ATL

Although I still enjoy flying Delta, the overall flying experience feels cheapened. But I guess that is true of most, if not all american carriers.

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Overall

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
8.0
Excellent

Jorge,Aug 2026

TPA - ATL

Although I still enjoy flying Delta, the overall flying experience feels cheapened. But I guess that is true of most, if not all american carriers.

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Overall

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
8.0
Excellent

Jorge,Aug 2026

TPA - ATL

Although I still enjoy flying Delta, the overall flying experience feels cheapened. But I guess that is true of most, if not all american carriers.

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Overall

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
8.0
Excellent

Jorge,Aug 2026

TPA - ATL

Although I still enjoy flying Delta, the overall flying experience feels cheapened. But I guess that is true of most, if not all american carriers.

Related info for your journey

  • 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 9 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 $404, American Airlines can have you in Chicago from Sioux Falls in 2h 02m. 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 38% 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: Copa Airlines (88%), Air New Zealand (79%), Iberia (64%).

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

    While on average a flight from Sioux Falls to Chicago is generally $1,714, our data shows the cheapest flight currently is $214. When looking at the most popular route, (Sioux Falls Joe Foss Field - Chicago O'Hare Intl), you can expect to pay $279 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, November is the cheapest month in which you can book a flight from Sioux Falls to Chicago (average of $236). Flying from Sioux Falls to Chicago in June is currently the most expensive (average of $364). 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
Merrillville
Lansing
Valparaiso
Hammond
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Porter

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Top 2 airlines flying from Sioux Falls to Chicago

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$329FlexibilityNo cancel feeOn-time69%

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