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$112+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
RAP — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Delta)

One-way from

$112
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$479

Good round-trip deal

$380 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Rapid City-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Rapid City-Chicago (CHI) flights.
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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. 11% potential increase in price ($51 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 October 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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/52:51 pmRAP - ORD
1 stop4h 04mDelta
Sun 12/76:00 amORD - RAP
1 stop5h 22mDelta
Deal found 10/28$229
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 12/96:05 amRAP - ORD
2 stops9h 54mDelta
Tue 12/166:00 amORD - RAP
1 stop5h 22mDelta
Deal found 10/28$234
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:30 pmRAP - ORD
Nonstop2h 27mUnited Airlines
Sat 11/157:10 amORD - RAP
1 stop4h 55mUnited Airlines
Deal found 10/27$239
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/511:02 amRAP - MDW
1 stop6h 16mDelta
Sun 12/77:02 pmMDW - RAP
1 stop4h 44mDelta
Deal found 10/28$249
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:18 pmRAP - ORD
1 stop6h 32mUnited Airlines
Mon 11/178:45 amORD - RAP
Nonstop2h 49mUnited Airlines
Deal found 10/29$259
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 11/142:51 pmRAP - ORD
1 stop5h 45mDelta
Sun 11/166:00 amORD - RAP
1 stop5h 27mDelta
Deal found 10/28$269
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 11/116:05 amRAP - MDW
1 stop6h 02mDelta
Sat 11/157:02 pmMDW - RAP
1 stop4h 37mDelta
Deal found 10/27$269
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 11/116:05 amRAP - ORD
1 stop4h 29mDelta
Sat 11/152:35 pmORD - RAP
2 stops9h 04mDelta
Deal found 10/27$274
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/102:55 pmRAP - ORD
1 stop5h 13mUnited Airlines
Mon 12/156:15 pmORD - RAP
1 stop5h 00mUnited Airlines
Deal found 10/28$276
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:30 pmRAP - ORD
Nonstop2h 27mUnited Airlines
Wed 11/128:45 amORD - RAP
Nonstop2h 49mUnited Airlines
Deal found 10/28$284
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:00 pmRAP - ORD
1 stop4h 59mUnited Airlines
Mon 11/248:45 amORD - RAP
Nonstop2h 49mUnited Airlines
Deal found 10/29$287
This Delta deal was found by Cheapflights users on 10/27. 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 11/86:05 amRAP - MDW
1 stop6h 03mDelta
Tue 11/119:41 amMDW - RAP
1 stop5h 30mDelta
Deal found 10/27$294

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 October 29, 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

Tue 1/20

12:35 pm-7:51 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 2/11

2:36 pm-7:18 pm

1 stop5h 42m

$229

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Tue 11/11

1:30 pm-4:57 pm

Nonstop2h 27m

Chicago O'Hare Intl

Sat 11/15

7:10 am-11:05 am

1 stop4h 55m

$239

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 2/28

6:20 am-11:33 am

1 stop4h 13m

Chicago O'Hare Intl

Mon 3/2

7:00 pm-10:14 pm

1 stop4h 14m

$249

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Fri 12/5

11:02 am-6:18 pm

1 stop6h 16m

Chicago Midway

Sun 12/7

7:02 pm-10:46 pm

1 stop4h 44m

$249

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 11/15

1:30 pm-4:57 pm

Nonstop2h 27m

Chicago O'Hare Intl

Mon 11/17

8:45 am-10:34 am

Nonstop2h 49m

$249

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 11/14

2:51 pm-9:36 pm

1 stop5h 45m

Chicago O'Hare Intl

Mon 11/17

6:00 am-10:27 am

1 stop5h 27m

$269

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 11/14

2:51 pm-9:36 pm

1 stop5h 45m

Chicago O'Hare Intl

Sun 11/16

6:00 am-10:27 am

1 stop5h 27m

$269

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 11/15

2:51 pm-9:36 pm

1 stop5h 45m

Chicago O'Hare Intl

Mon 11/17

6:00 am-10:27 am

1 stop5h 27m

$269

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 11/15

6:05 am-1:07 pm

1 stop6h 02m

Chicago Midway

Mon 11/17

9:41 am-3:45 pm

1 stop7h 04m

$269

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Tue 11/11

6:05 am-11:34 am

1 stop4h 29m

Chicago O'Hare Intl

Sat 11/15

2:35 pm-10:39 pm

2 stops9h 04m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 26 results
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Compare providers for flights from Rapid City to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Rapid City to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Rapid City-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Rapid City-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Rapid City-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Rapid City-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Rapid City-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, May is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $189). Flying from Rapid City to Chicago in February is currently the most expensive (average of $315). 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 October 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Rapid City to Chicago as you normally would.

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 October 29, 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
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 2 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 13m. Rapid City and Chicago are separated by a distance of 777 mi. This flight may include one or multiple stops.

  • 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 52% 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: Envoy Air (78%), American Airlines (71%), Qatar Airways (60%).

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

    On average you can expect to pay $401 for a flight from Rapid City to Chicago. The cheapest flight overall is $175 while the most popular route, (Rapid City - Chicago O'Hare Intl) is currently priced at $229.

  • 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, May is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $189). Flying from Rapid City to Chicago in February is currently the most expensive (average of $315). 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
Porter
Benton Harbor

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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 October 29, 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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