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$123+ Cheap flights from Rapid City (RAP) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
RAP — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Rapid City to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Rapid City (RAP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$229
(American Airlines)

One-way from

$123
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$302

Good round-trip deal

$351 or less

Good one-way deal

$203 or less
From Rapid City to Chicago (CHI)
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One-way flight from Rapid City to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Rapid City to Chicago (CHI).
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Price to beat on a one-way flight from Rapid City to Chicago (CHI).
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Find flight deals from Rapid City to Chicago

Cheapest flights from Rapid City to Chicago
Explore the most affordable flight options available from Rapid City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:58 pmRAP - ORD
1 stop5h 44mAmerican Airlines
Sun 10/265:00 amORD - RAP
1 stop7h 48mAmerican Airlines
Deal found 9/10$229
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:05 amRAP - MDW
1 stop6h 03mDelta
Wed 11/129:41 amMDW - RAP
1 stop7h 04mDelta
Deal found 9/11$229
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:02 amRAP - ORD
2 stops8h 29mDelta
Wed 12/1011:03 amORD - RAP
1 stop5h 42mDelta
Deal found 9/10$234
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2910:33 amRAP - MDW
2 stops10h 41mDelta
Sat 11/87:10 pmMDW - RAP
1 stop4h 26mDelta
Deal found 9/11$234
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2910:33 amRAP - ORD
2 stops12h 25mDelta
Sat 11/85:20 amORD - RAP
2 stops9h 25mDelta
Deal found 9/11$239
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2910:33 amRAP - ORD
1 stop5h 17mDelta
Thu 11/136:45 amORD - RAP
2 stops10h 00mDelta
Deal found 9/11$244
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:03 pmRAP - ORD
1 stop28h 42mMultiple Airlines
Tue 11/1111:00 amORD - RAP
1 stop23h 24mMultiple Airlines
Deal found 9/11$265
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:44 pmRAP - ORD
1 stop22h 59mMultiple Airlines
Wed 11/128:30 pmORD - RAP
1 stop25h 24mMultiple Airlines
Deal found 9/10$267
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:05 amRAP - MDW
1 stop6h 03mDelta
Thu 11/139:41 amMDW - RAP
1 stop7h 04mDelta
Deal found 9/11$269
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:44 pmRAP - ORD
1 stop31h 01mMultiple Airlines
Tue 11/1111:00 amORD - RAP
1 stop23h 24mMultiple Airlines
Deal found 9/11$270
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:34 pmRAP - ORD
1 stop3h 45mDelta
Wed 10/291:25 pmORD - RAP
2 stops10h 11mDelta
Deal found 9/11$274
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:03 pmRAP - ORD
1 stop28h 42mMultiple Airlines
Wed 11/128:30 pmORD - RAP
1 stop25h 24mMultiple Airlines
Deal found 9/11$281

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rapid City 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, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Rapid City to Chicago that are best for you.

Fly from

Rapid City

Fly to

Chicago

Route

Depart

Return

Price

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 12/5

4:25 pm-9:40 pm

1 stop4h 15m

Chicago O'Hare Intl

Tue 12/9

11:03 am-3:45 pm

1 stop5h 42m

$229

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 12/6

6:05 am-11:43 am

1 stop4h 38m

Chicago O'Hare Intl

Wed 12/10

11:03 am-3:45 pm

1 stop5h 42m

$229

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 10/29

6:05 am-1:08 pm

1 stop6h 03m

Chicago Midway

Wed 11/12

9:41 am-3:45 pm

1 stop7h 04m

$229

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 11/1

6:05 am-1:08 pm

1 stop6h 03m

Chicago Midway

Tue 11/11

9:41 am-2:11 pm

1 stop5h 30m

$229

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 11/1

6:05 am-1:08 pm

1 stop6h 03m

Chicago Midway

Sat 11/8

9:20 am-1:45 pm

1 stop5h 25m

$229

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Wed 10/29

10:33 am-5:43 pm

1 stop6h 10m

Chicago Midway

Tue 11/11

9:41 am-3:45 pm

1 stop7h 04m

$229

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Wed 10/29

10:33 am-11:58 pm

2 stops12h 25m

Chicago O'Hare Intl

Wed 11/12

8:50 am-2:11 pm

1 stop6h 21m

$234

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 12/5

4:25 pm-9:40 pm

1 stop4h 15m

Chicago O'Hare Intl

Wed 12/10

6:45 am-3:45 pm

2 stops10h 00m

$234

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 11/1

6:05 am-1:08 pm

1 stop6h 03m

Chicago Midway

Wed 11/12

9:32 am-3:45 pm

2 stops7h 13m

$234

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 11/1

6:05 am-6:49 pm

2 stops11h 44m

Chicago O'Hare Intl

Wed 11/12

8:55 am-3:45 pm

2 stops7h 50m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 32 results
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Best time to book a flight from Rapid City to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Rapid City with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Rapid City to Chicago

What is the cheapest month to book a flight from Rapid City to Chicago?

Currently, August is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $245). Flying from Rapid City to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RAP to CHI?

Find hourly flight availability from Rapid City to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s optimal to fly from Rapid City to Chicago in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Rapid City to Chicago

Explore weekly flight availability from Rapid City to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from RAP to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Rapid City to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 11, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Rapid City to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Rapid City to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Rapid City to Chicago?

    If you book a flight to Chicago from Rapid City, you will be flying from Rapid City, which is the city’s only airport. Rapid City (RAP) is located 9.0 mi from the center of Rapid City. There are 5 flights from Rapid City to Chicago per day from 3 different airlines.

  • How long is the flight from Rapid City to Chicago?

    Departing from Rapid City to Chicago will take you 4h 15m. Rapid City and Chicago are separated by a distance of 777 mi.

  • What are the cheapest airlines flying from Rapid City to Chicago round-trip?

    American Airlines, at $189, was found to be the cheapest airline from Rapid City to Chicago.Alternate airlines to your destination round-trip include United Airlines and Delta. American Airlines is currently priced 50% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Rapid City to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Rapid City to Chicago on time: Emirates (71%), Air New Zealand (71%), SkyWest Airlines (62%).

  • What are the cheapest flights from Rapid City to Chicago?

    On average you can expect to pay $541 for a flight from Rapid City to Chicago. The cheapest flight overall is $168 while the most popular route, (Rapid City - Chicago O'Hare Intl) is currently priced at $267.

  • Can I find deals for flights from Rapid City to Chicago that include hotel bookings?

    Yes. In addition to deals on Rapid City to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Rapid City to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Rapid City to Chicago.

  • Can I find deals for business class flights from Rapid City to Chicago?

    Yes. Cheapflights offers flight deals from Rapid City to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Rapid City to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $245). Flying from Rapid City to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Rapid City to Chicago

Discover the top 3 airlines that operate flights from Rapid City to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$219FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$210Average$351FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$358FlexibilityNo cancel feeOn-timeN/A

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