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$161 Cheap Flights from Roanoke (ROA) to Chicago (MDW)

View $161 flight on Fri, Sep 11, 2026Opens 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 $161 for one-way flights and $299 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Sep 6 - Tue, Sep 22
ROA
Roanoke
MDW
Chicago
$299 Roundtrip, found 7 hours ago
$299
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, Sep 6 from Roanoke to Chicago, returning Tue, Sep 22, priced at $299 found 7 hours ago
Delta
Sun, Sep 6 - Tue, Sep 22
ROA
Roanoke
MDW
Chicago
$300 Roundtrip, found 5 days ago
$300
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Sep 6 from Roanoke to Chicago, returning Tue, Sep 22, priced at $300 found 5 days ago
Delta
Sat, Aug 29 - Mon, Aug 31
ROA
Roanoke
MDW
Chicago
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 29 from Roanoke to Chicago, returning Mon, Aug 31, priced at $309 found 2 days ago
Delta
Tue, Aug 4 - Tue, Aug 11
ROA
Roanoke
MDW
Chicago
$319 Roundtrip, found 7 hours ago
$319
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Aug 4 from Roanoke to Chicago, returning Tue, Aug 11, priced at $319 found 7 hours ago
Delta
Fri, Aug 28 - Mon, Aug 31
ROA
Roanoke
MDW
Chicago
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 28 from Roanoke to Chicago, returning Mon, Aug 31, priced at $329 found 2 days ago
Delta
Sat, Oct 17 - Mon, Oct 19
ROA
Roanoke
MDW
Chicago
$334 Roundtrip, found 2 days ago
$334
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 17 from Roanoke to Chicago, returning Mon, Oct 19, priced at $334 found 2 days ago
Delta
Thu, Sep 10 - Mon, Sep 14
ROA
Roanoke
MDW
Chicago
$344 Roundtrip, found 16 hours ago
$344
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Sep 10 from Roanoke to Chicago, returning Mon, Sep 14, priced at $344 found 16 hours ago
Delta
Tue, Aug 4 - Tue, Aug 11
ROA
Roanoke
MDW
Chicago
$354 Roundtrip, found 7 hours ago
$354
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Aug 4 from Roanoke to Chicago, returning Tue, Aug 11, priced at $354 found 7 hours ago
Delta
Sun, Sep 6 - Tue, Sep 22
ROA
Roanoke
MDW
Chicago
$355 Roundtrip, found 5 days ago
$355
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Sep 6 from Roanoke to Chicago, returning Tue, Sep 22, priced at $355 found 5 days ago
Delta
Mon, Jul 27 - Wed, Aug 5
ROA
Roanoke
MDW
Chicago
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jul 27 from Roanoke to Chicago, returning Wed, Aug 5, priced at $364 found 1 day 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. Average driving time to city center is 23 minutes. Flights from $677
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $677

Frequently asked questions

How much does a flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $161 and cheap return flights from $299 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $389 and $986, and roundtrip flights usually range from $229 to $1250. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from ROA to MDW is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
Enter ROA to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting flights from Roanoke, VA (ROA) to Chicago, IL (MDW), starting from around $229. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Roanoke (ROA) to Chicago (MDW) usually departs at around 5:55 AM, operated by Delta. This is a seasonal service active in April, allowing you to make the most of your time in the Windy City. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Roanoke Regional (ROA) to Midway Intl. (MDW) are in the early morning, from 6am to 9am. About 69% of passengers prefer this time window. Many major carriers, including Delta and United Airlines, offer flights during this window. This timing is favored because it allows travelers to reach Chicago early in the day.
How long does it take to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
A flight from ROA to MDW with a layover takes around 7 hours, with the route covering approximately 516 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the ROA to MDW route with Delta Air Lines.
How do I earn miles on a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Roanoke Regional (ROA)?
From Roanoke Regional (ROA), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Philadelphia Intl. (PHL), LaGuardia (LGA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, 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 if you'd like more information.

Travel information

Origin airport
Roanoke Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$298
Distance
515 mi

Book with confidence

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 September. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $161 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.

 

Roanoke to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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