$170 Cheap Flights from Roanoke (ROA) to Chicago (MDW)

View $170 flight on Tue, Oct 28, 2025Opens in a new window

Popular airlines from Roanoke Regional Airport (ROA) to Chicago Midway Airport (MDW)

Cheap Flights from Roanoke to Chicago (ROA-MDW)

Prices were available within the past 7 days and start at $170 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 9 - Mon, Dec 29
ROA
Roanoke
MDW
Chicago
$229 Roundtrip, found 18 hours ago
$229
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Dec 9 from Roanoke to Chicago, returning Mon, Dec 29, priced at $229 found 18 hours ago
Delta
Tue, Dec 9 - Tue, Dec 30
ROA
Roanoke
MDW
Chicago
$239 Roundtrip, found 18 hours ago
$239
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Dec 9 from Roanoke to Chicago, returning Tue, Dec 30, priced at $239 found 18 hours ago
Delta
Thu, Feb 26 - Sat, Feb 28
ROA
Roanoke
MDW
Chicago
$249 Roundtrip, found 4 days ago
$249
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Feb 26 from Roanoke to Chicago, returning Sat, Feb 28, priced at $249 found 4 days ago
Delta
Tue, Nov 11 - Wed, Nov 19
ROA
Roanoke
MDW
Chicago
$267 Roundtrip, found 5 days ago
$267
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Roanoke to Chicago, returning Wed, Nov 19, priced at $267 found 5 days ago
Delta
Thu, Nov 27 - Mon, Dec 1
ROA
Roanoke
MDW
Chicago
$269 Roundtrip, found 7 hours ago
$269
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Nov 27 from Roanoke to Chicago, returning Mon, Dec 1, priced at $269 found 7 hours ago
Delta
Wed, Dec 10 - Tue, Dec 30
ROA
Roanoke
MDW
Chicago
$279 Roundtrip, found 18 hours ago
$279
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Dec 10 from Roanoke to Chicago, returning Tue, Dec 30, priced at $279 found 18 hours ago
Delta
Tue, Oct 7 - Tue, Oct 28
ROA
Roanoke
MDW
Chicago
$293 Roundtrip, found 3 days ago
$293
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 7 from Roanoke to Chicago, returning Tue, Oct 28, priced at $293 found 3 days ago
Delta
Mon, Nov 24 - Wed, Dec 3
ROA
Roanoke
MDW
Chicago
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 24 from Roanoke to Chicago, returning Wed, Dec 3, priced at $299 found 1 day ago
Delta
Mon, Dec 22 - Mon, Dec 29
ROA
Roanoke
MDW
Chicago
$302 Roundtrip, found 19 hours ago
$302
Roundtrip
found 19 hours ago
Select Delta flight, departing Mon, Dec 22 from Roanoke to Chicago, returning Mon, Dec 29, priced at $302 found 19 hours ago
Delta
Wed, Dec 17 - Mon, Dec 29
ROA
Roanoke
MDW
Chicago
$304 Roundtrip, found 19 hours ago
$304
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Dec 17 from Roanoke to Chicago, returning Mon, Dec 29, priced at $304 found 19 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $597
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $597
Flights from Roanoke (ROA) to Chicago (MDW)
Origin airport
Roanoke Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$228
Distance
515 mi

Roanoke to Chicago Flights

The cheapest times to fly from Roanoke 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 Roanoke to Chicago are during the month of December. You can find some of the cheapest flights from Roanoke to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Roanoke to Chicago

Sunday is one of the best days to book for cheap flights from Roanoke 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 Roanoke 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 Roanoke to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $170 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 Roanoke 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 Roanoke 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 Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $170 or cheap return flight from $229 from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW)?
December is the cheapest month to fly from ROA to MDW. Avoiding peak travel times is often the key to scoring lower fares.
What is the cheapest airline that flies from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from ROA to MDW, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights departing from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way in no time.
What day of the week has the most flights from ROA to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary based on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**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 Roanoke Regional Airport (ROA)?
Compare your flight options from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from ROA to MDW are usually more expensive. For the best rates, start looking for flights early. That being said, if you're flexible with your travel plans, it's possible to score a cheap ticket right before your trip.
Is it cheaper to book a ROA to MDW flight and hotel package?
You'll generally save money by booking a ROA to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. After selecting your preferred flights and accommodations, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Roanoke Regional Airport (ROA) to Midway Intl. Airport (MDW)?
Typically, you can modify or cancel your ROA to MDW flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want further information, head to our Customer Service portal.

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*Available to One Key members.