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$138+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
RAP — CHI
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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Cheap 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 April 28, 2026.

This United Airlines deal was found by Cheapflights users on 4/27. 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.
Wed 6/31:35 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Tue 6/95:00 am
ORD
-
RAP
1 stop5h 20m
United Airlines
Deal found 4/27$201
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 6/311:13 am
RAP
-
ORD
1 stop4h 38m
Delta
Tue 6/96:30 am
ORD
-
RAP
1 stop4h 57m
Delta
Deal found 4/27$211
This American Airlines deal was found by Cheapflights users on 4/25. 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 9/236:11 pm
RAP
-
ORD
Nonstop2h 19m
American Airlines
Mon 9/289:40 am
ORD
-
RAP
Nonstop2h 28m
American Airlines
Deal found 4/25$212
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 8/221:33 pm
RAP
-
ORD
Nonstop2h 23m
United Airlines
Tue 8/258:44 am
ORD
-
RAP
Nonstop2h 28m
United Airlines
Deal found 4/27$230
This United Airlines deal was found by Cheapflights users on 4/26. 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 7/151:35 pm
RAP
-
ORD
Nonstop2h 24m
United Airlines
Sun 7/195:00 am
ORD
-
RAP
1 stop5h 20m
United Airlines
Deal found 4/26$232
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 7/303:25 pm
RAP
-
ORD
Nonstop2h 38m
American Airlines
Mon 8/31:21 pm
ORD
-
RAP
Nonstop2h 34m
American Airlines
Deal found 4/25$233
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Sat 5/235:01 pm
RAP
-
ORD
1 stop6h 41m
American Airlines
Tue 5/269:45 am
ORD
-
RAP
Nonstop2h 34m
American Airlines
Deal found 4/25$240
This United Airlines deal was found by Cheapflights users on 4/23. 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 9/51:33 pm
RAP
-
ORD
Nonstop2h 23m
United Airlines
Tue 9/86:00 am
ORD
-
RAP
1 stop7h 24m
United Airlines
Deal found 4/23$242
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 5/213:23 pm
RAP
-
ORD
Nonstop2h 34m
American Airlines
Mon 5/259:45 am
ORD
-
RAP
Nonstop2h 34m
American Airlines
Deal found 4/25$251
This Delta deal was found by Cheapflights users on 4/24. 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 6/196:48 am
RAP
-
ORD
1 stop7h 17m
Delta
Mon 6/225:57 pm
ORD
-
RAP
1 stop5h 40m
Delta
Deal found 4/24$253
This Delta deal was found by Cheapflights users on 4/25. 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 5/306:50 am
RAP
-
MDW
1 stop5h 29m
Delta
Sat 6/279:54 am
MDW
-
RAP
1 stop6h 54m
Delta
Deal found 4/25$295
This Delta deal was found by Cheapflights users on 4/23. 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 9/510:40 am
RAP
-
MDW
1 stop6h 25m
Delta
Tue 9/86:45 pm
MDW
-
RAP
1 stop4h 13m
Delta
Deal found 4/23$324

Find 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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$201
(United Airlines)

One-way from

$138
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$510

Good round-trip deal

$365 or less

Good one-way deal

$260 or less
Provider with most accurate pricing for Rapid City-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Rapid City-Chicago (CHI) flights.
Search Deals
From Rapid City to Chicago (CHI)
Search Deals
One-way flight from Rapid City to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Rapid City to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Rapid City to Chicago (CHI).
Search Deals

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 April 28, 2026.
Use the filters below to find and compare flights from Rapid City to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 8/22

12:30 pm-6:27 pm

1 stop4h 57m

Chicago O'Hare Intl

Tue 8/25

5:45 pm-10:23 pm

1 stop5h 38m

$211

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Wed 6/10

1:35 pm-4:59 pm

Nonstop2h 24m

Chicago O'Hare Intl

Sun 6/14

5:00 am-9:20 am

1 stop5h 20m

$273
Quickest round-trip

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 6/5

1:35 pm-4:59 pm

Nonstop2h 24m

Chicago O'Hare Intl

Mon 6/8

8:45 am-10:24 am

Nonstop2h 39m

$278

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Wed 7/1

5:53 pm-12:44 am

1 stop5h 51m

Chicago O'Hare Intl

Sat 7/4

8:45 am-10:24 am

Nonstop2h 39m

$281

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Sat 5/30

6:50 am-1:19 pm

1 stop5h 29m

Chicago Midway

Sat 6/27

9:54 am-3:48 pm

1 stop6h 54m

$295

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 9/5

10:40 am-4:48 pm

1 stop5h 08m

Chicago O'Hare Intl

Tue 9/8

3:50 pm-9:58 pm

1 stop7h 08m

$324

Rapid CityChicago

RAP - MDW

RAPMDW

Rapid City

Fri 5/8

11:13 am-5:56 pm

1 stop5h 43m

Chicago Midway

Tue 5/12

7:13 pm-10:23 pm

1 stop4h 10m

$329

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 9/4

6:00 am-9:36 am

Nonstop2h 36m

Chicago O'Hare Intl

Mon 9/7

8:44 am-10:12 am

Nonstop2h 28m

$357

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Fri 7/10

5:53 pm-12:44 am

1 stop5h 51m

Chicago O'Hare Intl

Mon 7/13

5:00 am-9:20 am

1 stop5h 20m

$369

Rapid CityChicago

RAP - ORD

RAPORD

Rapid City

Sat 7/4

11:20 am-8:05 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 7/8

5:00 am-9:20 am

1 stop5h 20m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 37 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rapid City-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, July is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $190). Flying from Rapid City to Chicago in January is currently the most expensive (average of $248). 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 April 28, 2026.

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.

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 April 28, 2026.

The most flights from RAP to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 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 April 28, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican 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
8,467 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,467 reviews
Delta
7.9
Good
8,467 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,672 reviews
Delta
7.9
Good
8,467 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,677 reviews
Delta
7.9
Good
8,467 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 2 different airlines.

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

    Departing from Rapid City to Chicago will take you 4h 57m. 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 $187, was found to be the cheapest airline from Rapid City to Chicago. An alternate airline flying to your destination would be United Airlines. 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: Emirates (61%), United Airlines (61%), Air New Zealand (61%).

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

    On average you can expect to pay $381 for a flight from Rapid City to Chicago. The cheapest flight overall is $200 while the most popular route, (Rapid City - Chicago O'Hare Intl) is currently priced at $201.

  • 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, July is the cheapest month in which you can book a flight from Rapid City to Chicago (average of $190). Flying from Rapid City to Chicago in January is currently the most expensive (average of $248). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Rapid City to Chicago

Discover the top 2 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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$239FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$354FlexibilityNo cancel feeOn-time69%

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