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Cheap flights from Roanoke to Chicago from $289

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Roanoke to Chicago departing on 4/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Roanoke to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:21 pm - 12:25 am
MDW
-
ROA
6h 04m
1 stop
$289Delta
Tue, Apr 21 - Wed, Apr 29
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:21 pm - 12:25 am
MDW
-
ROA
6h 04m
1 stop
$291Delta
Tue, Apr 21 - Tue, Apr 21
Delta Logo
6:00 am - 11:56 am
ROA
-
MDW
6h 56m
1 stop
Delta Logo
5:25 pm - 11:49 pm
MDW
-
ROA
5h 24m
1 stop
$314Delta
Wed, Jun 17 - Wed, Jun 24
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:10 pm - 12:34 am
MDW
-
ROA
6h 24m
1 stop
$327Delta
Tue, May 5 - Mon, May 11
Delta Logo
6:00 am - 11:56 am
ROA
-
MDW
6h 56m
1 stop
Delta Logo
5:10 pm - 12:34 am
MDW
-
ROA
6h 24m
1 stop
$330Delta
Thu, May 7 - Mon, May 11
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:21 pm - 12:25 am
MDW
-
ROA
6h 04m
1 stop
$334Delta
Wed, Apr 22 - Wed, Apr 29
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:21 pm - 12:25 am
MDW
-
ROA
6h 04m
1 stop
$335Delta
Tue, Apr 14 - Wed, Apr 15
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
9:29 am - 11:13 pm
MDW
-
ROA
12h 44m
2 stops
$339Delta
Tue, Apr 21 - Wed, Apr 22
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
6:07 pm - 12:04 am
MDW
-
ROA
4h 57m
1 stop
$344Delta
Tue, Mar 24 - Wed, Apr 1
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
6:23 am - 2:50 pm
MDW
-
ROA
7h 27m
1 stop
$349Delta
Tue, May 5 - Sun, May 10

Delta flights from Roanoke to Chicago Midway Airport

Our best Delta deals on Roanoke to Chicago Midway Airport flight tickets
Delta
Apr 21
ROA6:00 amRoanoke
4h 56m
1 stop
MDW9:56 amChicago Midway
Apr 21
MDW5:21 pmChicago Midway
6h 04m
1 stop
ROA12:25 amRoanoke
$291
Delta
Jun 17
ROA6:00 amRoanoke
6h 56m
1 stop
MDW11:56 amChicago Midway
Jun 24
MDW5:25 pmChicago Midway
5h 24m
1 stop
ROA11:49 pmRoanoke
$314
Delta
May 5
ROA6:00 amRoanoke
4h 56m
1 stop
MDW9:56 amChicago Midway
May 11
MDW5:10 pmChicago Midway
6h 24m
1 stop
ROA12:34 amRoanoke
$327

momondo Fare Finder

 
Customize your flight search to find flights from Roanoke to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated March 14, 2026.
Use the filters below to find and compare flights from Roanoke to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 4/21

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 4/29

5:21 pm-12:25 am

1 stop6h 04m

$289

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 4/21

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Tue 4/21

5:21 pm-12:25 am

1 stop6h 04m

$291

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 6/17

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Wed 6/24

5:25 pm-11:49 pm

1 stop5h 24m

$314

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 5/5

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Mon 5/11

5:10 pm-12:34 am

1 stop6h 24m

$327

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Thu 5/7

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Mon 5/11

5:10 pm-12:34 am

1 stop6h 24m

$330

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 4/22

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 4/29

5:21 pm-12:25 am

1 stop6h 04m

$334

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 4/14

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 4/15

5:21 pm-12:25 am

1 stop6h 04m

$335

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 4/21

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 4/22

9:29 am-11:13 pm

2 stops12h 44m

$339
Quickest round-trip

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 3/24

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Wed 4/1

6:07 pm-12:04 am

1 stop4h 57m

$344

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 5/5

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Sun 5/10

6:23 am-2:50 pm

1 stop7h 27m

$349

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Roanoke to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Roanoke to Chicago Midway?

Delta is the most popular carrier operating from Roanoke to Chicago Midway

When to book flights from Roanoke to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Roanoke to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Roanoke to Chicago Midway Airport (ROA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Roanoke to Chicago Midway Airport

Fastest flight time

4h 51m

Direct flights

None
The fastest flight from Roanoke to Chicago Midway Airport takes 4h 51m
There are no direct flights from Roanoke to Chicago Midway Airport. There are no popular flight routes from Roanoke to Chicago Midway Airport.
Search flight deals

  • How far is Roanoke to Chicago Midway by plane?

    A flight from Roanoke to Chicago Midway will travel around 519.2 mi. Flights usually cover this in 4h 51m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Roanoke Airport to Chicago Midway Airport?

    Prices for flights from Roanoke Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Roanoke Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Roanoke Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Roanoke Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Roanoke to Chicago Midway Airport?

Best airlines flying from Roanoke to Chicago Midway Airport

Compare and see reviews for airlines that fly from Roanoke to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $228Free CancellationRating
7.9
8,291 reviews
Search Delta flights

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Why use momondo?

Why should I use momondo to find a flight deal from Roanoke to Chicago?

Finding the right flight to Chicago from Roanoke is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Roanoke to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Roanoke to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Roanoke to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Roanoke.

I’m not ready to book a flight from Roanoke to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Roanoke are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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