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Cheap flights from South Dakota to Chicago from $100

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 11/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
5:14 am - 9:19 amFSD-MDW
4h 05m1 stop
Delta Logo
1:50 pm - 7:40 pmMDW-FSD
5h 50m1 stop
$209Delta
Find Deal
Wed, Dec 3 - Sat, Dec 6
Delta Logo
5:15 am - 12:35 pmFSD-MDW
7h 20m2 stops
Delta Logo
9:20 am - 3:33 pmMDW-FSD
6h 13m1 stop
$214Delta
Find Deal
Wed, Feb 18 - Sat, Feb 21
Delta Logo
5:18 am - 12:46 pmFSD-MDW
7h 28m2 stops
Delta Logo
5:34 pm - 11:09 pmMDW-FSD
5h 35m1 stop
$219Delta
Find Deal
Sat, Nov 15 - Mon, Nov 17
Delta Logo
5:15 am - 8:54 amFSD-MDW
3h 39m1 stop
Delta Logo
9:20 am - 3:33 pmMDW-FSD
6h 13m1 stop
$224Delta
Find Deal
Wed, Feb 18 - Sat, Feb 21
Delta Logo
10:54 am - 6:36 pmRAP-MDW
6h 42m1 stop
Delta Logo
7:16 pm - 10:28 pmMDW-RAP
4h 12m1 stop
$229Delta
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Tue, Jan 20 - Tue, Jan 27
Delta Logo
5:18 am - 9:01 amFSD-MDW
3h 43m1 stop
Delta Logo
6:00 am - 4:52 pmMDW-FSD
10h 52m2 stops
$229Delta
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Wed, Nov 26 - Thu, Nov 27
Delta Logo
10:54 am - 6:36 pmRAP-MDW
6h 42m1 stop
Delta Logo
9:34 am - 3:25 pmMDW-RAP
6h 51m2 stops
$234Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27
Delta Logo
5:15 am - 12:35 pmFSD-MDW
7h 20m2 stops
Delta Logo
9:30 am - 3:33 pmMDW-FSD
6h 03m2 stops
$234Delta
Find Deal
Wed, Feb 18 - Sat, Feb 21
Frontier Logo
2:26 pm - 11:08 amFSD-MDW
20h 42m1 stop
Frontier Logo
10:50 pm - 7:55 pmMDW-FSD
21h 05m1 stop
$283Frontier
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Sun, Dec 14 - Sun, Dec 21
Multiple Airlines Logo
2:13 pm - 11:30 amFSD-MDW
21h 17m1 stop
Multiple Airlines Logo
3:10 pm - 9:22 amMDW-FSD
18h 12m2 stops
$295Multiple Airlines
Find Deal
Thu, Nov 13 - Thu, Dec 4

Frontier flights from South Dakota to Chicago Midway Airport

Our best Frontier deals on South Dakota to Chicago Midway Airport flight tickets
Frontier
Dec 14
FSD2:26 pmSioux Falls Joe Foss Field
20h 42m
1 stop
MDW11:08 amChicago Midway
Dec 21
MDW10:50 pmChicago Midway
21h 05m
1 stop
FSD7:55 pmSioux Falls Joe Foss Field
$283
Find similar
Frontier
Nov 7
FSD2:27 pmSioux Falls Joe Foss Field
22h 10m
2 stops
MDW12:37 pmChicago Midway
Nov 9
MDW12:30 pmChicago Midway
25h 17m
1 stop
FSD1:47 pmSioux Falls Joe Foss Field
$435
Find similar
Frontier
Oct 31
FSD2:32 pmSioux Falls Joe Foss Field
22h 05m
2 stops
MDW12:37 pmChicago Midway
Nov 2
MDW12:30 pmChicago Midway
25h 13m
1 stop
FSD1:43 pmSioux Falls Joe Foss Field
$586
Find similar

Delta flights from South Dakota to Chicago Midway Airport

Our best Delta deals on South Dakota to Chicago Midway Airport flight tickets
Delta
Dec 3
FSD5:14 amSioux Falls Joe Foss Field
4h 05m
1 stop
MDW9:19 amChicago Midway
Dec 6
MDW1:50 pmChicago Midway
5h 50m
1 stop
FSD7:40 pmSioux Falls Joe Foss Field
$209
Find similar
Delta
Feb 18
FSD5:15 amSioux Falls Joe Foss Field
7h 20m
2 stops
MDW12:35 pmChicago Midway
Feb 21
MDW9:20 amChicago Midway
6h 13m
1 stop
FSD3:33 pmSioux Falls Joe Foss Field
$214
Find similar
Delta
Nov 15
FSD5:18 amSioux Falls Joe Foss Field
7h 28m
2 stops
MDW12:46 pmChicago Midway
Nov 17
MDW5:34 pmChicago Midway
5h 35m
1 stop
FSD11:09 pmSioux Falls Joe Foss Field
$219
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from South Dakota to Chicago Midway Airport 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 October 30, 2025.
Use the filters below to find and compare flights from South Dakota to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 12/3

5:14 am-9:19 am

1 stop4h 05m

Chicago Midway

Sat 12/6

1:50 pm-7:40 pm

1 stop5h 50m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:15 am-12:35 pm

2 stops7h 20m

Chicago Midway

Sat 2/21

9:20 am-3:33 pm

1 stop6h 13m

$214

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 11/15

5:18 am-12:46 pm

2 stops7h 28m

Chicago Midway

Mon 11/17

5:34 pm-11:09 pm

1 stop5h 35m

$219

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:15 am-8:54 am

1 stop3h 39m

Chicago Midway

Sat 2/21

9:20 am-3:33 pm

1 stop6h 13m

$224

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Tue 1/20

10:54 am-6:36 pm

1 stop6h 42m

Chicago Midway

Tue 1/27

7:16 pm-10:28 pm

1 stop4h 12m

$229

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 11/26

5:18 am-9:01 am

1 stop3h 43m

Chicago Midway

Thu 11/27

6:00 am-4:52 pm

2 stops10h 52m

$229

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Tue 1/20

10:54 am-6:36 pm

1 stop6h 42m

Chicago Midway

Tue 1/27

9:34 am-3:25 pm

2 stops6h 51m

$234

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:15 am-12:35 pm

2 stops7h 20m

Chicago Midway

Sat 2/21

9:30 am-3:33 pm

2 stops6h 03m

$234

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sun 12/14

2:26 pm-11:08 am

1 stop20h 42m

Chicago Midway

Sun 12/21

10:50 pm-7:55 pm

1 stop21h 05m

$283

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 11/13

2:13 pm-11:30 am

1 stop21h 17m

Chicago Midway

Thu 12/4

3:10 pm-9:22 am

2 stops18h 12m

$295

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 Midway Airport

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 time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from South Dakota in the morning is the least expensive time of day to depart. momondo users have found prices as low as $408 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $598. Of course, these prices can vary depending on the time of year and what airport you fly to.

Cheap South Dakota to Chicago Midway Airport flight deals and tips

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

Direct flights

None
There are no direct flights from South Dakota to Chicago Midway Airport. There are no popular flight routes from South Dakota to Chicago Midway Airport.
Search flight deals

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

    Prices for flights from South Dakota to Chicago Midway Airport are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from South Dakota to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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
Crown Point
Munster
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 collates all your flight options in one place and lets you filter them to find the perfect flight from South Dakota to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from South Dakota to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight 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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from South Dakota and alert you when they change.

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