$99 Cheap Flights from Richmond (RIC) to Chicago (MDW)

View $99 flight on Sat, May 31, 2025Opens in a new window

Popular airlines from Richmond Intl. Airport (RIC) to Chicago Midway Airport (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Richmond to Chicago (RIC-MDW)

Prices were available within the past 7 days and start at $99 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jul 1 - Sat, Jul 12
RIC
Richmond
MDW
Chicago
$199 Roundtrip, found 12 hours ago
$199
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Jul 1 from Richmond to Chicago, returning Sat, Jul 12, priced at $199 found 12 hours ago
Delta
Wed, Jul 30 - Tue, Aug 5
RIC
Richmond
MDW
Chicago
$201 Roundtrip, found 14 hours ago
$201
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, Jul 30 from Richmond to Chicago, returning Tue, Aug 5, priced at $201 found 14 hours ago
Southwest Airlines
Thu, Jun 5 - Sat, Jun 14
RIC
Richmond
MDW
Chicago
$243 Roundtrip, found 14 hours ago
$243
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Richmond to Chicago, returning Sat, Jun 14, priced at $243 found 14 hours ago
Delta
Thu, Jun 5 - Sat, Jun 14
RIC
Richmond
MDW
Chicago
$253 Roundtrip, found 14 hours ago
$253
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Jun 5 from Richmond to Chicago, returning Sat, Jun 14, priced at $253 found 14 hours ago
Southwest Airlines
Thu, Jun 5 - Sat, Jun 14
RIC
Richmond
MDW
Chicago
$253 Roundtrip, found 14 hours ago
$253
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Richmond to Chicago, returning Sat, Jun 14, priced at $253 found 14 hours ago
Southwest Airlines
Sat, May 24 - Tue, May 27
RIC
Richmond
MDW
Chicago
$253 Roundtrip, found 5 hours ago
$253
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from Richmond to Chicago, returning Tue, May 27, priced at $253 found 5 hours ago
Southwest Airlines
Sat, May 24 - Tue, May 27
RIC
Richmond
MDW
Chicago
$263 Roundtrip, found 5 hours ago
$263
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from Richmond to Chicago, returning Tue, May 27, priced at $263 found 5 hours ago
Southwest Airlines
Wed, May 28 - Sat, May 31
RIC
Richmond
MDW
Chicago
$266 Roundtrip, found 2 hours ago
$266
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Richmond to Chicago, returning Sat, May 31, priced at $266 found 2 hours ago
Southwest Airlines
Fri, Jun 6 - Sat, Jun 14
RIC
Richmond
MDW
Chicago
$267 Roundtrip, found 14 hours ago
$267
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Fri, Jun 6 from Richmond to Chicago, returning Sat, Jun 14, priced at $267 found 14 hours ago
Delta
Tue, Jul 1 - Sat, Jul 12
RIC
Richmond
MDW
Chicago
$269 Roundtrip, found 12 hours ago
$269
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Jul 1 from Richmond to Chicago, returning Sat, Jul 12, priced at $269 found 12 hours ago
Flights from Richmond (RIC) to Chicago (MDW)
Origin airport
Richmond Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$196
Distance
627 mi

Richmond to Chicago Flights

The cheapest times to fly from Richmond to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Richmond to Chicago are during the month of July. You can find some of the cheapest flights from Richmond to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Richmond to Chicago

Sunday is one of the best days to book for cheap flights from Richmond to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Richmond to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Richmond to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Richmond to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Richmond to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW) cost?
Grab cheap return fares starting at $253 from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving RIC on May 20 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from RIC to MDW?
The cheapest flights from RIC to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
When setting off from Richmond Intl. Airport (RIC), you can catch a nonstop flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from RIC to MDW?
With fares starting at $127 for a one-way journey from RIC to MDW, Southwest Airlines is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from RIC on May 20 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
On average you can take your pick of 6 direct flights per week from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW). For more options, consider flights with layovers. Just enter your details on Expedia and then set the filter tool to include one stop or more.
What are the most popular departure times for flights from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
The 7 AM departures from RIC to MDW are the most sought after. Prices can be higher for these popular slots. If you want to save money, book during off-peak hours.
What day of the week has the most flights from RIC to MDW?
If you depart on a Friday, you’ll get the widest range of options for flights from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW).
What is the earliest flight from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 7:50AM UTC-5, leaving from Richmond Intl. Airport (RIC). You’ll be flying for about 2h 15m, reaching Midway Intl. Airport (MDW) at approximately 9:05AM UTC-6.
How long does it take to fly from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
Flights from RIC to MDW have an average travel time of 2 hours and 15 minutes. The distance between the two is 630 mi.
What airline has the least delays from RIC to MDW?
With 85% of flights usually arriving as scheduled, Southwest Airlines has the best on-time performance for nonstop flights from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW). To monitor your flight status and receive notifications about any changes, simply head to the Expedia App.
What is the best time to fly from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, opt for a flight that leaves Richmond Intl. Airport (RIC) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Richmond Intl. Airport (RIC)?
You’ll touch down at O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Richmond Intl. Airport (RIC).
Is it cheaper to buy a plane ticket from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from RIC to MDW just before your getaway is generally more expensive. However, if there’s some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a RIC to MDW flight and hotel package?
Opting for a RIC to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our impressive range of stays and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Richmond Intl. Airport (RIC) to Midway Intl. Airport (MDW)?
If you booked your RIC to MDW flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.