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Cheap flights from South Dakota to Chicago from $188

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 7/7. 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
1 adult, Economy, 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
1:20 pm - 6:05 pm
FSD
-
MDW
4h 45m
1 stop
Delta Logo
6:45 pm - 10:46 pm
MDW
-
FSD
4h 01m
1 stop
$269Delta
Fri, Sep 11 - Sun, Sep 13
Delta Logo
1:26 pm - 6:01 pm
FSD
-
MDW
4h 35m
1 stop
Delta Logo
7:25 pm - 10:51 pm
MDW
-
FSD
3h 26m
1 stop
$279Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
1:13 pm - 5:54 pm
FSD
-
MDW
4h 41m
1 stop
Delta Logo
6:55 pm - 10:54 pm
MDW
-
FSD
3h 59m
1 stop
$284Delta
Sat, Jun 20 - Sat, Jun 27
Delta Logo
1:13 pm - 5:54 pm
FSD
-
MDW
4h 41m
1 stop
Delta Logo
6:55 pm - 10:54 pm
MDW
-
FSD
3h 59m
1 stop
$294Delta
Sat, Jun 20 - Sat, Jun 27
Delta Logo
6:48 am - 1:09 pm
RAP
-
MDW
5h 21m
1 stop
Delta Logo
7:06 pm - 10:26 pm
MDW
-
RAP
4h 20m
1 stop
$300Delta
Wed, Jul 15 - Mon, Jul 20
Delta Logo
5:00 am - 8:37 am
FSD
-
MDW
3h 37m
1 stop
Delta Logo
6:55 pm - 10:52 pm
MDW
-
FSD
3h 57m
1 stop
$314Delta
Wed, Jul 29 - Sat, Aug 1
Delta Logo
1:26 pm - 6:01 pm
FSD
-
MDW
4h 35m
1 stop
Delta Logo
7:25 pm - 10:51 pm
MDW
-
FSD
3h 26m
1 stop
$324Delta
Thu, Sep 3 - Mon, Sep 7
Delta Logo
11:00 am - 6:18 pm
RAP
-
MDW
6h 18m
1 stop
Delta Logo
9:54 am - 3:29 pm
MDW
-
RAP
6h 35m
1 stop
$328Delta
Tue, Jun 30 - Sat, Jul 18
Delta Logo
1:13 pm - 5:54 pm
FSD
-
MDW
4h 41m
1 stop
Delta Logo
7:16 pm - 11:12 pm
MDW
-
FSD
3h 56m
1 stop
$329Delta
Sat, Jun 20 - Fri, Jun 26
Delta Logo
5:00 am - 8:39 am
FSD
-
MDW
3h 39m
1 stop
Delta Logo
7:25 pm - 10:51 pm
MDW
-
FSD
3h 26m
1 stop
$369Delta
Fri, Sep 4 - Mon, Sep 7

Delta flights from South Dakota to Chicago Midway Airport

Our best Delta deals on South Dakota to Chicago Midway Airport flight tickets
Delta
Sep 11
FSD1:20 pmSioux Falls Joe Foss Field
4h 45m
1 stop
MDW6:05 pmChicago Midway
Sep 13
MDW6:45 pmChicago Midway
4h 01m
1 stop
FSD10:46 pmSioux Falls Joe Foss Field
$269
Delta
Jun 29
FSD1:53 pmSioux Falls Joe Foss Field
4h 25m
1 stop
MDW6:18 pmChicago Midway
Jul 3
MDW9:54 amChicago Midway
5h 50m
1 stop
FSD3:44 pmSioux Falls Joe Foss Field
$279
Delta
Jun 20
FSD1:13 pmSioux Falls Joe Foss Field
4h 41m
1 stop
MDW5:54 pmChicago Midway
Jun 27
MDW6:55 pmChicago Midway
3h 59m
1 stop
FSD10:54 pmSioux Falls Joe Foss Field
$284

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 June 6, 2026.
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

Cheapest round-trip

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 9/11

1:20 pm-6:05 pm

1 stop4h 45m

Chicago Midway

Sun 9/13

6:45 pm-10:46 pm

1 stop4h 01m

$269

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 8/21

1:26 pm-6:01 pm

1 stop4h 35m

Chicago Midway

Mon 8/24

7:25 pm-10:51 pm

1 stop3h 26m

$279

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 6/20

1:13 pm-5:54 pm

1 stop4h 41m

Chicago Midway

Sat 6/27

6:55 pm-10:54 pm

1 stop3h 59m

$284

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 6/20

1:13 pm-5:54 pm

1 stop4h 41m

Chicago Midway

Sat 6/27

6:55 pm-10:54 pm

1 stop3h 59m

$294

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 7/15

6:48 am-1:09 pm

1 stop5h 21m

Chicago Midway

Mon 7/20

7:06 pm-10:26 pm

1 stop4h 20m

$300

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 7/29

5:00 am-8:37 am

1 stop3h 37m

Chicago Midway

Sat 8/1

6:55 pm-10:52 pm

1 stop3h 57m

$314

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 9/3

1:26 pm-6:01 pm

1 stop4h 35m

Chicago Midway

Mon 9/7

7:25 pm-10:51 pm

1 stop3h 26m

$324

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Tue 6/30

11:00 am-6:18 pm

1 stop6h 18m

Chicago Midway

Sat 7/18

9:54 am-3:29 pm

1 stop6h 35m

$328

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sat 6/20

1:13 pm-5:54 pm

1 stop4h 41m

Chicago Midway

Fri 6/26

7:16 pm-11:12 pm

1 stop3h 56m

$329
Quickest round-trip

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 9/4

5:00 am-8:39 am

1 stop3h 39m

Chicago Midway

Mon 9/7

7:25 pm-10:51 pm

1 stop3h 26m

$369

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 airline that flies from South Dakota to Chicago Midway?

Allegiant Air and Delta are the most popular carriers operating from South Dakota to Chicago Midway

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

Fastest flight time

3h 37m

Direct flights

None
The fastest flight from South Dakota to Chicago Midway Airport takes 3h 37m
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

Frequently asked questions about flying from South Dakota to Chicago Midway Airport

  • 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
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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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