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Cheap flights from South Dakota to Chicago from $103

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 5/8. 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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0 bags

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Find the cheapest flights from South Dakota to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:44 pm - 6:36 pm
FSD
-
MDW
4h 52m
1 stop
Delta Logo
7:16 pm - 11:02 pm
MDW
-
FSD
3h 46m
1 stop
$167Delta
Tue, Apr 21 - Sat, Apr 25
Delta Logo
8:05 am - 11:34 am
FSD
-
ORD
3h 29m
1 stop
Delta Logo
5:43 pm - 10:57 pm
ORD
-
FSD
5h 14m
1 stop
$167Delta
Thu, Apr 30 - Sat, May 9
Delta Logo
5:05 am - 12:43 pm
FSD
-
MDW
7h 38m
2 stops
Delta Logo
7:16 pm - 11:02 pm
MDW
-
FSD
3h 46m
1 stop
$172Delta
Tue, Apr 21 - Sat, Apr 25
Delta Logo
8:05 am - 11:34 am
FSD
-
ORD
3h 29m
1 stop
Delta Logo
1:44 pm - 10:57 pm
ORD
-
FSD
9h 13m
2 stops
$172Delta
Thu, Apr 30 - Sat, May 9
American Airlines Logo
2:06 pm - 3:52 pm
FSD
-
ORD
1h 46mnonstop
American Airlines Logo
5:11 pm - 7:09 pm
ORD
-
FSD
1h 58mnonstop
$189American Airlines
Fri, Apr 3 - Tue, Apr 7
United Airlines Logo
7:43 am - 9:35 am
FSD
-
ORD
1h 52mnonstop
United Airlines Logo
8:10 pm - 10:02 pm
ORD
-
FSD
1h 52mnonstop
$203United Airlines
Sat, Mar 7 - Sun, Mar 8
United Airlines Logo
7:40 am - 9:32 am
FSD
-
ORD
1h 52mnonstop
United Airlines Logo
8:10 pm - 10:02 pm
ORD
-
FSD
1h 52mnonstop
$204United Airlines
Fri, Feb 27 - Sun, Mar 8
American Airlines Logo
11:53 am - 3:20 pm
RAP
-
ORD
2h 27mnonstop
American Airlines Logo
9:45 am - 11:23 am
ORD
-
RAP
2h 38mnonstop
$209American Airlines
Tue, Apr 7 - Mon, Apr 13
American Airlines Logo
1:08 pm - 10:45 pm
RAP
-
ORD
8h 37m
1 stop
American Airlines Logo
9:45 am - 11:23 am
ORD
-
RAP
2h 38mnonstop
$219American Airlines
Tue, Apr 7 - Mon, Apr 13
United Airlines Logo
6:45 pm - 8:35 pm
FSD
-
ORD
1h 50mnonstop
United Airlines Logo
8:45 am - 10:46 am
ORD
-
FSD
2h 01mnonstop
$219United Airlines
Sat, Feb 21 - Wed, Feb 25

American Airlines flights from South Dakota to Chicago

Our best American Airlines deals on South Dakota to Chicago flight tickets
American Airlines
Apr 3
FSD2:06 pmSioux Falls Joe Foss Field
1h 46m
ORD3:52 pmChicago O'Hare Intl
Apr 7
ORD5:11 pmChicago O'Hare Intl
1h 58m
FSD7:09 pmSioux Falls Joe Foss Field
$189
American Airlines
Apr 7
RAP11:53 amRapid City
2h 27m
ORD3:20 pmChicago O'Hare Intl
Apr 13
ORD9:45 amChicago O'Hare Intl
2h 38m
RAP11:23 amRapid City
$209
American Airlines
Apr 7
RAP1:08 pmRapid City
8h 37m
1 stop
ORD10:45 pmChicago O'Hare Intl
Apr 13
ORD9:45 amChicago O'Hare Intl
2h 38m
RAP11:23 amRapid City
$219

United Airlines flights from South Dakota to Chicago

Our best United Airlines deals on South Dakota to Chicago flight tickets
United Airlines
Mar 7
FSD7:43 amSioux Falls Joe Foss Field
1h 52m
ORD9:35 amChicago O'Hare Intl
Mar 8
ORD8:10 pmChicago O'Hare Intl
1h 52m
FSD10:02 pmSioux Falls Joe Foss Field
$203
United Airlines
Feb 27
FSD7:40 amSioux Falls Joe Foss Field
1h 52m
ORD9:32 amChicago O'Hare Intl
Mar 8
ORD8:10 pmChicago O'Hare Intl
1h 52m
FSD10:02 pmSioux Falls Joe Foss Field
$204
United Airlines
Feb 21
FSD6:45 pmSioux Falls Joe Foss Field
1h 50m
ORD8:35 pmChicago O'Hare Intl
Feb 25
ORD8:45 amChicago O'Hare Intl
2h 01m
FSD10:46 amSioux Falls Joe Foss Field
$219

momondo 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, momondo users made 832,500 searches. Data last updated February 9, 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

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Tue 4/21

1:44 pm-6:36 pm

1 stop4h 52m

Chicago Midway

Sat 4/25

7:16 pm-11:02 pm

1 stop3h 46m

$167

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 4/30

8:05 am-11:34 am

1 stop3h 29m

Chicago O'Hare Intl

Sat 5/9

5:43 pm-10:57 pm

1 stop5h 14m

$167

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Tue 4/21

5:05 am-12:43 pm

2 stops7h 38m

Chicago Midway

Sat 4/25

7:16 pm-11:02 pm

1 stop3h 46m

$172

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Thu 4/30

8:05 am-11:34 am

1 stop3h 29m

Chicago O'Hare Intl

Sat 5/9

1:44 pm-10:57 pm

2 stops9h 13m

$172

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 4/3

2:06 pm-3:52 pm

Nonstop1h 46m

Chicago O'Hare Intl

Tue 4/7

5:11 pm-7:09 pm

Nonstop1h 58m

$189

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 3/7

7:43 am-9:35 am

Nonstop1h 52m

Chicago O'Hare Intl

Sun 3/8

8:10 pm-10:02 pm

Nonstop1h 52m

$203

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Fri 2/27

7:40 am-9:32 am

Nonstop1h 52m

Chicago O'Hare Intl

Sun 3/8

8:10 pm-10:02 pm

Nonstop1h 52m

$204

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Tue 4/7

11:53 am-3:20 pm

Nonstop2h 27m

Chicago O'Hare Intl

Mon 4/13

9:45 am-11:23 am

Nonstop2h 38m

$209

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Tue 4/7

1:08 pm-10:45 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 4/13

9:45 am-11:23 am

Nonstop2h 38m

$219

Sioux FallsChicago

FSD - ORD

FSDORD

Sioux Falls Joe Foss Field

Sat 2/21

6:45 pm-8:35 pm

Nonstop1h 50m

Chicago O'Hare Intl

Wed 2/25

8:45 am-10:46 am

Nonstop2h 01m

$219

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from South Dakota, with most prices found around $246. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from South Dakota to Chicago during January average around $249.

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 $399. 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 $618.

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 at noon. Flights from South Dakota to Chicago during this time can be as low as $364. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $497.

What is the cheapest South Dakota to Chicago flight route?

Fly from Rapid City 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 $294 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.

Can stopping save me money on South Dakota to Chicago flights?

No. A direct flight is the cheapest option for a flight between South Dakota 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

$245

Fastest flight time

1h 46m

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 $245. The best round-trip flight deal from South Dakota to Chicago found on momondo in the last 72 hours is $339.
The fastest flight from South Dakota to Chicago takes 1h 46m
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?

  • 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?

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 ConnectionPriceFrom $178Free CancellationRating
8.0
22 reviews
Search Denver Air Connection flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
11,260 reviews
Search American Airlines flights
United AirlinesPriceFrom $189Free CancellationRating
7.4
9,266 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport