Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Roanoke to Chicago from $152

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Roanoke to Chicago departing on 9/25. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Roanoke to Chicago

Cheap round-trip flights

Delta Logo
3:42 pm - 10:14 pmROA-MDW
7h 32m1 stop
Delta Logo
5:34 pm - 12:21 amMDW-ROA
5h 47m1 stop
$229Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
6:00 am - 9:51 amROA-MDW
4h 51m1 stop
Delta Logo
5:34 pm - 12:21 amMDW-ROA
5h 47m1 stop
$239Delta
Find Deal
Sun, Nov 16 - Tue, Nov 25
Logo
9:49 pm - 9:47 amROA-MDW
12h 58m1 stop
Logo
5:20 am - 8:30 pmMDW-ROA
14h 10m1 stop
$246
Find Deal
Wed, Oct 8 - Sun, Oct 12
Logo
9:49 pm - 4:42 pmROA-MDW
19h 53m2 stops
Logo
5:20 am - 8:30 pmMDW-ROA
14h 10m1 stop
$265
Find Deal
Wed, Oct 8 - Sun, Oct 12
Delta Logo
7:59 pm - 8:40 amROA-MDW
13h 41m2 stops
Delta Logo
5:34 pm - 12:21 amMDW-ROA
5h 47m1 stop
$267Delta
Find Deal
Mon, Nov 3 - Tue, Nov 11
Delta Logo
6:00 am - 9:40 amROA-MDW
4h 40m1 stop
Delta Logo
4:23 pm - 12:09 amMDW-ROA
6h 46m1 stop
$269Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
Delta Logo
3:42 pm - 10:14 pmROA-MDW
7h 32m1 stop
Delta Logo
9:35 am - 10:45 pmMDW-ROA
12h 10m2 stops
$277Delta
Find Deal
Sat, Oct 11 - Tue, Oct 14
Delta Logo
3:31 pm - 9:10 pmROA-MDW
6h 39m1 stop
Delta Logo
6:30 pm - 12:25 amMDW-ROA
4h 55m1 stop
$279Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
6:00 am - 6:25 pmROA-MDW
13h 25m2 stops
Delta Logo
4:23 pm - 12:09 amMDW-ROA
6h 46m1 stop
$287Delta
Find Deal
Tue, Nov 4 - Sat, Nov 8
Delta Logo
3:42 pm - 10:14 pmROA-MDW
7h 32m1 stop
Delta Logo
9:35 am - 10:45 pmMDW-ROA
12h 10m2 stops
$297Delta
Find Deal
Sat, Oct 11 - Wed, Oct 15

Delta flights from Roanoke to Chicago Midway Airport

Our best Delta deals on Roanoke to Chicago Midway Airport flight tickets
Delta
Nov 8
ROA3:42 pmRoanoke
7h 32m
1 stop
MDW10:14 pmChicago Midway
Nov 11
MDW5:34 pmChicago Midway
5h 47m
1 stop
ROA12:21 amRoanoke
$229
Find similar
Delta
Nov 16
ROA6:00 amRoanoke
4h 51m
1 stop
MDW9:51 amChicago Midway
Nov 25
MDW5:34 pmChicago Midway
5h 47m
1 stop
ROA12:21 amRoanoke
$239
Find similar
Delta
Nov 3
ROA7:59 pmRoanoke
13h 41m
2 stops
MDW8:40 amChicago Midway
Nov 11
MDW5:34 pmChicago Midway
5h 47m
1 stop
ROA12:21 amRoanoke
$267
Find similar

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 September 15, 2025.
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

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 11/8

3:42 pm-10:14 pm

1 stop7h 32m

Chicago Midway

Tue 11/11

5:34 pm-12:21 am

1 stop5h 47m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sun 11/16

6:00 am-9:51 am

1 stop4h 51m

Chicago Midway

Tue 11/25

5:34 pm-12:21 am

1 stop5h 47m

$239

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 10/8

9:49 pm-9:47 am

1 stop12h 58m

Chicago Midway

Sun 10/12

5:20 am-8:30 pm

1 stop14h 10m

$246

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 10/8

9:49 pm-4:42 pm

2 stops19h 53m

Chicago Midway

Sun 10/12

5:20 am-8:30 pm

1 stop14h 10m

$265

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Mon 11/3

7:59 pm-8:40 am

2 stops13h 41m

Chicago Midway

Tue 11/11

5:34 pm-12:21 am

1 stop5h 47m

$267

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 10/7

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sat 10/11

4:23 pm-12:09 am

1 stop6h 46m

$269

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 10/11

3:42 pm-10:14 pm

1 stop7h 32m

Chicago Midway

Tue 10/14

9:35 am-10:45 pm

2 stops12h 10m

$277

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 9/27

3:31 pm-9:10 pm

1 stop6h 39m

Chicago Midway

Tue 9/30

6:30 pm-12:25 am

1 stop4h 55m

$279

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 11/4

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

Sat 11/8

4:23 pm-12:09 am

1 stop6h 46m

$287

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 10/11

3:42 pm-10:14 pm

1 stop7h 32m

Chicago Midway

Wed 10/15

9:35 am-10:45 pm

2 stops12h 10m

$297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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?

Allegiant Air and Delta are the most popular carriers 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

Direct flights

None
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 19m, 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
7,954 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 10/15
Wed 10/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago