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Cheap flights from Sioux Falls to Chicago from $209

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Sioux Falls to Chicago departing on 2/18. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:00 am - 9:06 am
FSD
-
MDW
4h 06m1 stop
Delta Logo
11:45 am - 3:35 pm
MDW
-
FSD
3h 50m1 stop
$209Delta
Wed, Feb 18 - Sat, Feb 21
Delta Logo
5:00 am - 9:06 am
FSD
-
MDW
4h 06m1 stop
Delta Logo
9:34 am - 3:35 pm
MDW
-
FSD
6h 01m2 stops
$214Delta
Wed, Feb 18 - Sat, Feb 21
Delta Logo
1:00 pm - 6:37 pm
FSD
-
MDW
5h 37m1 stop
Delta Logo
11:45 am - 3:35 pm
MDW
-
FSD
3h 50m1 stop
$224Delta
Fri, Feb 13 - Sun, Feb 15
Delta Logo
1:00 pm - 6:37 pm
FSD
-
MDW
5h 37m1 stop
Delta Logo
9:34 am - 3:35 pm
MDW
-
FSD
6h 01m2 stops
$229Delta
Wed, Feb 18 - Sat, Feb 21
Delta Logo
10:50 am - 5:37 pm
FSD
-
MDW
6h 47m2 stops
Delta Logo
9:34 am - 3:35 pm
MDW
-
FSD
6h 01m2 stops
$234Delta
Thu, Feb 19 - Sat, Feb 21
Delta Logo
11:06 am - 5:19 pm
FSD
-
MDW
6h 13m1 stop
Delta Logo
5:59 pm - 11:08 pm
MDW
-
FSD
5h 09m1 stop
$254Delta
Sun, Dec 21 - Sat, Jan 3
Delta Logo
10:50 am - 5:37 pm
FSD
-
MDW
6h 47m2 stops
Delta Logo
11:45 am - 3:35 pm
MDW
-
FSD
3h 50m1 stop
$259Delta
Thu, Feb 19 - Sat, Feb 21
Delta Logo
5:00 am - 12:46 pm
FSD
-
MDW
7h 46m2 stops
Delta Logo
9:34 am - 3:35 pm
MDW
-
FSD
6h 01m2 stops
$264Delta
Wed, Feb 18 - Sat, Feb 21
Delta Logo
5:00 am - 11:06 am
FSD
-
MDW
6h 06m1 stop
Delta Logo
5:59 pm - 11:08 pm
MDW
-
FSD
5h 09m1 stop
$269Delta
Fri, Jan 2 - Sun, Jan 4
Delta Logo
5:00 am - 12:46 pm
FSD
-
MDW
7h 46m2 stops
Delta Logo
9:34 am - 3:35 pm
MDW
-
FSD
6h 01m2 stops
$279Delta
Wed, Feb 18 - Sat, Feb 21

Delta flights from Sioux Falls to Chicago Midway Airport

Our best Delta deals on Sioux Falls to Chicago Midway Airport flight tickets
Delta
Feb 18
FSD5:00 amSioux Falls Joe Foss Field
4h 06m
1 stop
MDW9:06 amChicago Midway
Feb 21
MDW11:45 amChicago Midway
3h 50m
1 stop
FSD3:35 pmSioux Falls Joe Foss Field
$209
Find similar
Delta
Feb 18
FSD5:00 amSioux Falls Joe Foss Field
4h 06m
1 stop
MDW9:06 amChicago Midway
Feb 21
MDW9:34 amChicago Midway
6h 01m
2 stops
FSD3:35 pmSioux Falls Joe Foss Field
$214
Find similar
Delta
Feb 13
FSD1:00 pmSioux Falls Joe Foss Field
5h 37m
1 stop
MDW6:37 pmChicago Midway
Feb 15
MDW11:45 amChicago Midway
3h 50m
1 stop
FSD3:35 pmSioux Falls Joe Foss Field
$224
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Sioux Falls 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 December 9, 2025.
Use the filters below to find and compare flights from Sioux Falls 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 2/18

5:00 am-9:06 am

1 stop4h 06m

Chicago Midway

Sat 2/21

11:45 am-3:35 pm

1 stop3h 50m

$209

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:00 am-9:06 am

1 stop4h 06m

Chicago Midway

Sat 2/21

9:34 am-3:35 pm

2 stops6h 01m

$214

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 2/13

1:00 pm-6:37 pm

1 stop5h 37m

Chicago Midway

Sun 2/15

11:45 am-3:35 pm

1 stop3h 50m

$224

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

1:00 pm-6:37 pm

1 stop5h 37m

Chicago Midway

Sat 2/21

9:34 am-3:35 pm

2 stops6h 01m

$229

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 2/19

10:50 am-5:37 pm

2 stops6h 47m

Chicago Midway

Sat 2/21

9:34 am-3:35 pm

2 stops6h 01m

$234

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Sun 12/21

11:06 am-5:19 pm

1 stop6h 13m

Chicago Midway

Sat 1/3

5:59 pm-11:08 pm

1 stop5h 09m

$254

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Thu 2/19

10:50 am-5:37 pm

2 stops6h 47m

Chicago Midway

Sat 2/21

11:45 am-3:35 pm

1 stop3h 50m

$259

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:00 am-12:46 pm

2 stops7h 46m

Chicago Midway

Sat 2/21

9:34 am-3:35 pm

2 stops6h 01m

$264

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Fri 1/2

5:00 am-11:06 am

1 stop6h 06m

Chicago Midway

Sun 1/4

5:59 pm-11:08 pm

1 stop5h 09m

$269

Sioux FallsChicago

FSD - MDW

FSDMDW

Sioux Falls Joe Foss Field

Wed 2/18

5:00 am-12:46 pm

2 stops7h 46m

Chicago Midway

Sat 2/21

9:34 am-3:35 pm

2 stops6h 01m

$279

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 Sioux Falls 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 Sioux Falls 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.

When to book flights from Sioux Falls to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sioux Falls to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sioux Falls to Chicago Midway Airport (FSD to MDW) flight deals and tips

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

Fastest flight time

3h 23m

Direct flights

None
The fastest flight from Sioux Falls to Chicago Midway Airport takes 3h 23m
There are no direct flights from Sioux Falls to Chicago Midway Airport. There are no popular flight routes from Sioux Falls to Chicago Midway Airport.
Search flight deals

  • How far is Sioux Falls Joe Foss Field to Chicago Midway by plane?

    A flight from Sioux Falls Joe Foss Field to Chicago Midway will travel around 471.8 mi. 3h 33m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Sioux Falls Joe Foss Field Airport to Chicago Midway Airport?

    Prices for flights from Sioux Falls Joe Foss Field Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Sioux Falls Joe Foss Field Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sioux Falls Joe Foss Field Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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 Sioux Falls to Chicago?

It is quick and easy to find Sioux Falls to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Sioux Falls to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Sioux Falls to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Sioux Falls to Chicago?

Once all potential Sioux Falls 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 Sioux Falls to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Sioux Falls are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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