What airlines fly to Chicago?

United Airlines, American Airlines and Denver Air Connection are the top three most popular airlines that fly to Chicago from South Dakota according to our data. United Airlines is the first choice among our users, with 61% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from South Dakota to Chicago on average per day?

As of December 2025, there are 13 flights per day flying from South Dakota to Chicago. The most common time of day flights depart is 7:00AM, with 56% of flights taking off at noon.

How long does it take to fly to Chicago?

Average flight duration from South Dakota to Chicago depends on which airport you fly into and out of. Flying from Sioux Falls to Chicago O'Hare Intl Airport is 1h 42m on average, while flying from Rapid City to Chicago O'Hare Intl Airport is 2h 13m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How many flights depart from South Dakota to Chicago on average per week?

As of December 2025, there are 97 flights per week flying from South Dakota to Chicago. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

What is the cheapest airline that flies from South Dakota to Chicago?

Frontier and Delta are the most popular carriers operating from South Dakota to Chicago

When did momondo last update prices for flights from South Dakota to Chicago?

Prices for flights from South Dakota to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from South Dakota to Chicago?

As of December 2025, there are 3 operators available to choose from for flights from South Dakota to Chicago.

How old do you have to be to fly from South Dakota to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from South Dakota to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$87 Cheap Flights from South Dakota to Chicago in 2025/26

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:11 pm - 5:10 pm

FSD

ORD

1h 59mnonstop

8:45 am - 10:47 am

ORD

FSD

2h 02mnonstop

$189United Airlines

ter, jan 20 - ter, jan 27

6:29 pm - 8:26 pm

FSD

ORD

1h 57mnonstop

8:24 pm - 10:15 pm

ORD

FSD

1h 51mnonstop

$197United Airlines

qua, abr 22 - qui, mai 14

6:25 am - 11:05 am

FSD

MDW

4h 40m1 stop

7:16 pm - 11:04 pm

MDW

FSD

3h 48m1 stop

$209Delta

sáb, jan 10 - dom, jan 11

1:00 pm - 6:01 pm

FSD

ORD

5h 01m1 stop

8:50 am - 3:34 pm

ORD

FSD

6h 44m1 stop

$209Delta

qua, fev 18 - sáb, fev 21

12:10 pm - 3:23 pm

RAP

ORD

2h 13mnonstop

9:00 am - 10:31 am

ORD

RAP

2h 31mnonstop

$209United Airlines

qui, mai 7 - dom, mai 10

1:02 pm - 6:36 pm

FSD

MDW

5h 34m1 stop

9:32 am - 3:37 pm

MDW

FSD

6h 05m2 stops

$214Delta

ter, jan 20 - ter, jan 27

10:55 am - 6:59 pm

FSD

ORD

8h 04m2 stops

8:50 am - 3:34 pm

ORD

FSD

6h 44m1 stop

$214Delta

qui, fev 19 - sáb, fev 21

5:25 pm - 11:57 pm

RAP

ORD

5h 32m1 stop

9:00 am - 10:31 am

ORD

RAP

2h 31mnonstop

$219United Airlines

qui, mai 7 - dom, mai 10

7:30 am - 9:32 am

FSD

ORD

2h 02mnonstop

7:58 pm - 9:50 pm

ORD

FSD

1h 52mnonstop

$222United Airlines

sáb, jan 10 - dom, jan 11

7:01 pm - 11:22 am

FSD

ORD

16h 21m1 stop

3:00 pm - 4:07 pm

ORD

FSD

25h 07m2 stops

$243Multiple Airlines

seg, fev 2 - dom, fev 8

United Airlines flights from South Dakota to Chicago

Our best United Airlines deals on South Dakota to Chicago flight tickets

United Airlines

Jan 20

FSD3:11 pmSioux Falls Joe Foss Field

1h 59m

ORD5:10 pmChicago O'Hare Intl

Jan 27

ORD8:45 amChicago O'Hare Intl

2h 02m

FSD10:47 amSioux Falls Joe Foss Field

$189

Find similar

United Airlines

May 7

RAP12:10 pmRapid City

2h 13m

ORD3:23 pmChicago O'Hare Intl

May 10

ORD9:00 amChicago O'Hare Intl

2h 31m

RAP10:31 amRapid City

$209

Find similar

United Airlines

May 7

RAP5:25 pmRapid City

5h 32m

1 stop

ORD11:57 pmChicago O'Hare Intl

May 10

ORD9:00 amChicago O'Hare Intl

2h 31m

RAP10:31 amRapid City

$219

Find similar

Delta flights from South Dakota to Chicago

Our best Delta deals on South Dakota to Chicago flight tickets

Delta

Feb 18

FSD1:00 pmSioux Falls Joe Foss Field

5h 01m

1 stop

ORD6:01 pmChicago O'Hare Intl

Feb 21

ORD8:50 amChicago O'Hare Intl

6h 44m

1 stop

FSD3:34 pmSioux Falls Joe Foss Field

$209

Find similar

Delta

Feb 19

FSD10:55 amSioux Falls Joe Foss Field

8h 04m

2 stops

ORD6:59 pmChicago O'Hare Intl

Feb 21

ORD8:50 amChicago O'Hare Intl

6h 44m

1 stop

FSD3:34 pmSioux Falls Joe Foss Field

$214

Find similar

Delta

Mar 14

FSD1:34 pmSioux Falls Joe Foss Field

6h 15m

1 stop

ORD7:49 pmChicago O'Hare Intl

Mar 17

ORD8:55 amChicago O'Hare Intl

3h 58m

1 stop

FSD12:53 pmSioux Falls Joe Foss Field

$224

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

ter 1/20

3:11 pm-5:10 pm

Nonstop1h 59m

Chicago O'Hare Intl

ter 1/27

8:45 am-10:47 am

Nonstop2h 02m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

qua 4/22

6:29 pm-8:26 pm

Nonstop1h 57m

Chicago O'Hare Intl

qui 5/14

8:24 pm-10:15 pm

Nonstop1h 51m

$197

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

sáb 1/10

6:25 am-11:05 am

1 stop4h 40m

Chicago Midway

dom 1/11

7:16 pm-11:04 pm

1 stop3h 48m

$209

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

qua 2/18

1:00 pm-6:01 pm

1 stop5h 01m

Chicago O'Hare Intl

sáb 2/21

8:50 am-3:34 pm

1 stop6h 44m

$209

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

qui 5/7

12:10 pm-3:23 pm

Nonstop2h 13m

Chicago O'Hare Intl

dom 5/10

9:00 am-10:31 am

Nonstop2h 31m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

ter 1/20

1:02 pm-6:36 pm

1 stop5h 34m

Chicago Midway

ter 1/27

9:32 am-3:37 pm

2 stops6h 05m

$214

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

qui 2/19

10:55 am-6:59 pm

2 stops8h 04m

Chicago O'Hare Intl

sáb 2/21

8:50 am-3:34 pm

1 stop6h 44m

$214

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

qui 5/7

5:25 pm-11:57 pm

1 stop5h 32m

Chicago O'Hare Intl

dom 5/10

9:00 am-10:31 am

Nonstop2h 31m

$219

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

sáb 1/10

7:30 am-9:32 am

Nonstop2h 02m

Chicago O'Hare Intl

dom 1/11

7:58 pm-9:50 pm

Nonstop1h 52m

$222

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

seg 2/2

7:01 pm-11:22 am

1 stop16h 21m

Chicago O'Hare Intl

dom 2/8

3:00 pm-4:07 pm

2 stops25h 07m

$243

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How to get the cheapest flight ticket from South Dakota to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from South Dakota, with most prices found around $236. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from South Dakota to Chicago during September average around $246.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $411. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from South Dakota to Chicago for around $590.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from South Dakota to Chicago during this time can be as low as $373. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $493.

What is the cheapest South Dakota to Chicago flight route?

Fly from Watertown to Chicago O'Hare Intl for the best South Dakota - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from South Dakota when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $283 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from South Dakota for as low as $203 on momondo.

What cabin class options are available on South Dakota to Chicago flights?

There are 4 cabin classes available to choose from on South Dakota to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap South Dakota to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from South Dakota to Chicago

Best Price Found	$258
Fastest flight time	1h 42m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from South Dakota in the past 72 hours is $258. The best round-trip flight deal from South Dakota to Chicago found on momondo in the last 72 hours is $336.

The fastest flight from South Dakota to Chicago takes 1h 42m

Direct flights go from South Dakota to Chicago every day.

There are 3 airports in Chicago. From South Dakota there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

When did momondo last update prices for flights from South Dakota to Chicago?
Prices for flights from South Dakota to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from South Dakota to Chicago?
As of December 2025, there are 3 operators available to choose from for flights from South Dakota to Chicago.
How old do you have to be to fly from South Dakota to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from South Dakota to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from South Dakota to Chicago?
momondo data reveals that the most frequently booked plane model on the route from South Dakota to Chicago is Canadair (Bombardier) Regional Jet CRJ-550, representing 21.74% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 700 at 18.84%, Boeing 737-800 at 14.08%, and Embraer 175 (Enhanced Winglets) at 9.11%.

Best airlines flying from South Dakota to Chicago

Compare and see reviews for airlines that fly from South Dakota to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Denver Air Connection	PriceFrom $178	Free Cancellation	Rating 8.7 20 reviews	Search Denver Air Connection flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
United Airlines	PriceFrom $189	Free Cancellation	Rating 7.4 9,105 reviews	Search United Airlines flights
Delta	PriceFrom $228	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from South Dakota to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from South Dakota to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from South Dakota to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from South Dakota on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from South Dakota to Chicago?

Once all potential South Dakota to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from South Dakota to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from South Dakota to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Cheap flights from South Dakota to Chicago from $87

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from South Dakota to Chicago departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from South Dakota to Chicago

Our best United Airlines deals on South Dakota to Chicago flight tickets

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Our best Delta deals on South Dakota to Chicago flight tickets

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How to get the cheapest flight ticket from South Dakota to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from South Dakota to Chicago during this time can be as low as $373. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $493.

What is the cheapest South Dakota to Chicago flight route?

Fly from Watertown to Chicago O'Hare Intl for the best South Dakota - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on South Dakota to Chicago flights?

There are 4 cabin classes available to choose from on South Dakota to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from South Dakota to Chicago?

Frontier and Delta are the most popular carriers operating from South Dakota to Chicago

What airlines fly to Chicago?

How many flights depart from South Dakota to Chicago on average per day?

As of December 2025, there are 13 flights per day flying from South Dakota to Chicago. The most common time of day flights depart is 7:00AM, with 56% of flights taking off at noon.

How many flights depart from South Dakota to Chicago on average per week?

As of December 2025, there are 97 flights per week flying from South Dakota to Chicago. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

How long does it take to fly to Chicago?

Cheap South Dakota to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from South Dakota to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from South Dakota to Chicago?

How many operators does momondo search for flights from South Dakota to Chicago?

How old do you have to be to fly from South Dakota to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from South Dakota to Chicago?

Best airlines flying from South Dakota to Chicago

Compare and see reviews for airlines that fly from South Dakota to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from South Dakota to Chicago?

Can I find flights from South Dakota to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from South Dakota to Chicago?

I’m not ready to book a flight from South Dakota to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago