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Cheap flights from Asheville to Chicago from $103

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Asheville to Chicago departing on 4/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 9:54 am
AVL
-
MDW
4h 54m
1 stop
Delta Logo
6:00 am - 1:18 pm
MDW
-
AVL
6h 18m
1 stop
$229Delta
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 2:26 pm
AVL
-
MDW
9h 26m
1 stop
Multiple Airlines Logo
7:30 am - 9:27 pm
MDW
-
AVL
12h 57m
2 stops
$243Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
6:00 am - 2:26 pm
AVL
-
MDW
9h 26m
1 stop
Multiple Airlines Logo
8:00 am - 10:17 pm
MDW
-
AVL
13h 17m
1 stop
$248Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Delta Logo
5:40 am - 9:56 am
AVL
-
MDW
5h 16m
1 stop
Delta Logo
6:00 am - 11:03 am
MDW
-
AVL
4h 03m
1 stop
$249Delta
Sat, Apr 11 - Sun, Apr 19
Multiple Airlines Logo
6:00 am - 2:26 pm
AVL
-
MDW
9h 26m
1 stop
Multiple Airlines Logo
7:30 am - 9:27 pm
MDW
-
AVL
12h 57m
2 stops
$253Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
6:30 am - 2:26 pm
AVL
-
MDW
8h 56m
1 stop
Multiple Airlines Logo
9:04 pm - 11:36 pm
MDW
-
AVL
25h 32m
2 stops
$254Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
6:30 am - 2:26 pm
AVL
-
MDW
8h 56m
1 stop
Multiple Airlines Logo
6:00 am - 11:06 pm
MDW
-
AVL
16h 06m
2 stops
$263Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
2:23 pm - 5:45 pm
AVL
-
MDW
4h 22m
1 stop
Delta Logo
6:00 am - 1:36 pm
MDW
-
AVL
6h 36m
1 stop
$269Delta
Fri, Feb 20 - Sun, Feb 22
Delta Logo
5:40 am - 9:56 am
AVL
-
MDW
5h 16m
1 stop
Delta Logo
7:16 pm - 12:16 pm
MDW
-
AVL
16h 00m
1 stop
$274Delta
Sat, Apr 11 - Mon, Apr 20
Delta Logo
2:08 pm - 5:22 pm
AVL
-
MDW
4h 14m
1 stop
Delta Logo
6:00 am - 11:03 am
MDW
-
AVL
4h 03m
1 stop
$284Delta
Thu, Apr 9 - Mon, Apr 13

Delta flights from Asheville to Chicago Midway Airport

Our best Delta deals on Asheville to Chicago Midway Airport flight tickets
Delta
Mar 5
AVL6:00 amAsheville Regional
4h 54m
1 stop
MDW9:54 amChicago Midway
Mar 9
MDW6:00 amChicago Midway
6h 18m
1 stop
AVL1:18 pmAsheville Regional
$229
Delta
Apr 11
AVL5:40 amAsheville Regional
5h 16m
1 stop
MDW9:56 amChicago Midway
Apr 19
MDW6:00 amChicago Midway
4h 03m
1 stop
AVL11:03 amAsheville Regional
$249
Delta
Feb 19
AVL6:00 amAsheville Regional
4h 54m
1 stop
MDW9:54 amChicago Midway
Feb 23
MDW12:45 pmChicago Midway
4h 21m
1 stop
AVL6:06 pmAsheville Regional
$269

Allegiant Air flights from Asheville to Chicago Midway Airport

Our best Allegiant Air deals on Asheville to Chicago Midway Airport flight tickets
Allegiant Air
Jun 5
AVL2:04 pmAsheville Regional
1h 44m
MDW2:48 pmChicago Midway
Jun 8
MDW3:38 pmChicago Midway
1h 39m
AVL6:17 pmAsheville Regional
$120
Allegiant Air
Jun 15
AVL6:46 pmAsheville Regional
1h 44m
MDW7:30 pmChicago Midway
Jun 19
MDW8:20 pmChicago Midway
1h 39m
AVL10:59 pmAsheville Regional
$130
Allegiant Air
Jun 15
AVL6:46 pmAsheville Regional
1h 44m
MDW7:30 pmChicago Midway
Jun 19
MDW9:23 pmChicago Midway
15h 55m
2 stops
AVL2:18 pmAsheville Regional
$394

momondo Fare Finder

 
Customize your flight search to find flights from Asheville 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 February 5, 2026.
Use the filters below to find and compare flights from Asheville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 3/5

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 3/9

6:00 am-1:18 pm

1 stop6h 18m

$229

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 3/5

6:00 am-2:26 pm

1 stop9h 26m

Chicago Midway

Sun 3/8

7:30 am-9:27 pm

2 stops12h 57m

$243

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 3/5

6:00 am-2:26 pm

1 stop9h 26m

Chicago Midway

Sun 3/8

8:00 am-10:17 pm

1 stop13h 17m

$248

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Sat 4/11

5:40 am-9:56 am

1 stop5h 16m

Chicago Midway

Sun 4/19

6:00 am-11:03 am

1 stop4h 03m

$249

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 3/5

6:00 am-2:26 pm

1 stop9h 26m

Chicago Midway

Sun 3/8

7:30 am-9:27 pm

2 stops12h 57m

$253

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 2/26

6:30 am-2:26 pm

1 stop8h 56m

Chicago Midway

Sun 3/1

9:04 pm-11:36 pm

2 stops25h 32m

$254

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 2/19

6:30 am-2:26 pm

1 stop8h 56m

Chicago Midway

Mon 2/23

6:00 am-11:06 pm

2 stops16h 06m

$263

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 2/20

2:23 pm-5:45 pm

1 stop4h 22m

Chicago Midway

Sun 2/22

6:00 am-1:36 pm

1 stop6h 36m

$269

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Sat 4/11

5:40 am-9:56 am

1 stop5h 16m

Chicago Midway

Mon 4/20

7:16 pm-12:16 pm

1 stop16h 00m

$274

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 4/9

2:08 pm-5:22 pm

1 stop4h 14m

Chicago Midway

Mon 4/13

6:00 am-11:03 am

1 stop4h 03m

$284

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Asheville 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 day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Asheville. The lowest ticket price found for a Wednesday departure recently was $56. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Asheville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $109.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Asheville in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $90 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $127. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Asheville Regional to Chicago Midway flight route?

Fly from Asheville Regional to Chicago Midway for the best Asheville Regional - Chicago Midway flight prices

What cabin class options are available on Asheville Regional to Chicago Midway flights?

There is only 1 cabin class available to choose from on Asheville Regional to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Asheville to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Asheville to Chicago Midway Airport.

When to book flights from Asheville to Chicago Midway Airport

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

Cheap Asheville to Chicago Midway Airport (AVL to MDW) flight deals and tips

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

Fastest flight time

4h 14m

Direct flights

Tue and Sat
The fastest flight from Asheville to Chicago Midway Airport takes 4h 14m
Direct flights go from Asheville to Chicago Midway Airport on Tuesday and Saturday. There are no airlines offering direct flights.
Search flight deals

  • How far is Asheville Regional to Chicago Midway by plane?

    The distance between Asheville Regional and Chicago Midway is about 510.7 mi. A reasonable flight in good conditions will take 4h 14m.

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

    Prices for flights from Asheville Regional Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Asheville Regional Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Asheville to Chicago Midway Airport?

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

Best airlines flying from Asheville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Asheville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $58Free CancellationRating
7.2
709 reviews
Search Allegiant Air 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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Asheville to Chicago. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search for Asheville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Asheville and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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