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Cheap flights from Rapid City to Chicago from $224

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Rapid City to Chicago departing on 9/29. 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

Find the cheapest flights from Rapid City to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:46 am - 6:01 pm
RAP
-
MDW
6h 15m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$280Delta
Sat, Aug 8 - Sun, Aug 9
Delta Logo
10:55 am - 6:01 pm
RAP
-
MDW
6h 06m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$344Delta
Fri, Aug 7 - Sun, Aug 9
Delta Logo
10:46 am - 6:01 pm
RAP
-
MDW
6h 15m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$368Delta
Tue, Aug 4 - Wed, Aug 12
Delta Logo
10:55 am - 6:01 pm
RAP
-
MDW
6h 06m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$399Delta
Fri, Aug 7 - Sun, Aug 9
Delta Logo
6:48 am - 1:10 pm
RAP
-
MDW
5h 22m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$425Delta
Wed, Aug 19 - Mon, Aug 24
Delta Logo
11:00 am - 5:52 pm
RAP
-
MDW
5h 52m
1 stop
Delta Logo
9:54 am - 3:29 pm
MDW
-
RAP
6h 35m
1 stop
$474Delta
Sat, Jul 18 - Wed, Jul 22
Delta Logo
10:46 am - 6:01 pm
RAP
-
MDW
6h 15m
1 stop
Delta Logo
9:59 am - 3:49 pm
MDW
-
RAP
6h 50m
1 stop
$527Delta
Mon, Aug 24 - Thu, Aug 27
Delta Logo
6:48 am - 1:10 pm
RAP
-
MDW
5h 22m
1 stop
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$573Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
10:46 am - 6:01 pm
RAP
-
MDW
6h 15m
1 stop
Delta Logo
9:24 am - 3:49 pm
MDW
-
RAP
7h 25m
2 stops
$577Delta
Tue, Aug 4 - Wed, Aug 12
Delta Logo
6:48 am - 6:33 pm
RAP
-
MDW
10h 45m
2 stops
Delta Logo
7:25 pm - 10:37 pm
MDW
-
RAP
4h 12m
1 stop
$578Delta
Wed, Aug 19 - Mon, Aug 24

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Delta flights from Rapid City to Chicago Midway Airport

Our best Delta deals on Rapid City to Chicago Midway Airport flight tickets
Delta
Aug 8
RAP10:46 amRapid City
6h 15m
1 stop
MDW6:01 pmChicago Midway
Aug 9
MDW7:25 pmChicago Midway
4h 12m
1 stop
RAP10:37 pmRapid City
$280
Delta
Aug 7
RAP10:55 amRapid City
6h 06m
1 stop
MDW6:01 pmChicago Midway
Aug 9
MDW7:25 pmChicago Midway
4h 12m
1 stop
RAP10:37 pmRapid City
$344
Delta
Aug 4
RAP10:46 amRapid City
6h 15m
1 stop
MDW6:01 pmChicago Midway
Aug 12
MDW7:25 pmChicago Midway
4h 12m
1 stop
RAP10:37 pmRapid City
$368

momondo Fare Finder

 
Customize your flight search to find flights from Rapid City 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 July 2, 2026.
Use the filters below to find and compare flights from Rapid City to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 8/8

10:46 am-6:01 pm

1 stop6h 15m

Chicago Midway

Sun 8/9

7:25 pm-10:37 pm

1 stop4h 12m

$280

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Fri 8/7

10:55 am-6:01 pm

1 stop6h 06m

Chicago Midway

Sun 8/9

7:25 pm-10:37 pm

1 stop4h 12m

$344

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Tue 8/4

10:46 am-6:01 pm

1 stop6h 15m

Chicago Midway

Wed 8/12

7:25 pm-10:37 pm

1 stop4h 12m

$368

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Fri 8/7

10:55 am-6:01 pm

1 stop6h 06m

Chicago Midway

Sun 8/9

7:25 pm-10:37 pm

1 stop4h 12m

$399
Quickest round-trip

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 8/19

6:48 am-1:10 pm

1 stop5h 22m

Chicago Midway

Mon 8/24

7:25 pm-10:37 pm

1 stop4h 12m

$425

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 7/18

11:00 am-5:52 pm

1 stop5h 52m

Chicago Midway

Wed 7/22

9:54 am-3:29 pm

1 stop6h 35m

$474

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Mon 8/24

10:46 am-6:01 pm

1 stop6h 15m

Chicago Midway

Thu 8/27

9:59 am-3:49 pm

1 stop6h 50m

$527

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Thu 8/27

6:48 am-1:10 pm

1 stop5h 22m

Chicago Midway

Mon 8/31

7:25 pm-10:37 pm

1 stop4h 12m

$573

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Tue 8/4

10:46 am-6:01 pm

1 stop6h 15m

Chicago Midway

Wed 8/12

9:24 am-3:49 pm

2 stops7h 25m

$577

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 8/19

6:48 am-6:33 pm

2 stops10h 45m

Chicago Midway

Mon 8/24

7:25 pm-10:37 pm

1 stop4h 12m

$578

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 Rapid City 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 Rapid City to Chicago Midway?

Delta and Allegiant Air are the most popular carriers operating from Rapid City to Chicago Midway

When to book flights from Rapid City to Chicago Midway Airport

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

Cheap Rapid City to Chicago Midway Airport (RAP to MDW) flight deals and tips

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

Fastest flight time

3h 58m

Direct flights

None
The fastest flight from Rapid City to Chicago Midway Airport takes 3h 58m
There are no direct flights from Rapid City to Chicago Midway Airport. There are no popular flight routes from Rapid City to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Rapid City to Chicago Midway Airport

  • How far is Rapid City to Chicago Midway by plane?

    Rapid City and Chicago Midway are 797.4 mi apart from one another. A reasonable flight in good conditions will take 3h 58m.

  • When did momondo last update prices for flights from Rapid City Airport to Chicago Midway Airport?

    Prices for flights from Rapid City Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Rapid City Airport to Chicago Midway Airport?

    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 Rapid City Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek 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
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Hammond
Portage
Benton Harbor
Saint Joseph
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Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Rapid City to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Rapid City to Chicago for you.

Can I find flights from Rapid City to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Rapid City which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Rapid City to Chicago?

Once all potential Rapid City 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 Rapid City 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 Rapid City and alert you when they change.

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