Cheap Southwest Airlines flights Rapid City (RAP) to Chicago (ORD)

Finding cheap one-way Southwest Airlines flights from RAP to ORD on Expedia is a breeze — just filter by “Price (lowest to highest).” Alternatively, check out our budget-friendly round-trip fares for your next adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines flights to Chicago are often more affordable in the low-season months of January and February. Whether you’re in search of a round-trip or one-way ticket, you could land a better deal then.

To find cheap Southwest Airlines fares from Rapid City Regional Airport (RAP) to O’Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect what you pay. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To figure out if there’s a direct route from RAP to ORD with Southwest Airlines or any other carriers, check the “Nonstop” box when searching for flights.

Sort your results by “Early Morning” and “Morning” to find the earliest flights from RAP to ORD. Setting off early means you’re 20% less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Southwest Airlines flights from Rapid City Regional Airport (RAP) to Chicago arrive at O’Hare Intl. Airport (ORD). This is the main gateway to this city.

It’s usually possible to reschedule or cancel your flight, although there may be a charge if you booked more than 24 hours ago. Need to keep your options open? Apply the “No cancel fee” or “Changes included” filter to find flights that won’t charge you extra if you need to alter your plans. To update your itinerary, go to “Trips,” select your flight and click on “Manage Booking” for more information.