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Cheap flights from Asheville to Chicago from $49

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 9/19. 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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Find the cheapest flights from Asheville to Chicago (AVL-MDW)

Cheap round-trip flights

Allegiant Air Logo
11:21 am - 12:00 pmAVL-MDW
1h 39mnonstop
Allegiant Air Logo
5:33 pm - 8:10 pmMDW-AVL
1h 37mnonstop
$109Allegiant Air
Find Deal
Mon, Sep 22 - Fri, Sep 26
Allegiant Air Logo
4:04 pm - 4:43 pmAVL-MDW
1h 39mnonstop
Allegiant Air Logo
12:50 pm - 3:27 pmMDW-AVL
1h 37mnonstop
$128Allegiant Air
Find Deal
Fri, Sep 26 - Mon, Sep 29
Logo
4:21 pm - 5:02 pmAVL-MDW
1h 41mnonstop
Logo
6:06 pm - 8:25 amMDW-AVL
13h 19m1 stop
$165
Find Deal
Fri, Oct 31 - Sun, Nov 2
Logo
6:06 pm - 9:12 amAVL-MDW
16h 06m1 stop
Logo
5:52 pm - 8:29 pmMDW-AVL
1h 37mnonstop
$170
Find Deal
Wed, Oct 29 - Fri, Oct 31
Logo
4:21 pm - 5:02 pmAVL-MDW
1h 41mnonstop
Logo
3:40 pm - 8:45 pmMDW-AVL
28h 05m1 stop
$172
Find Deal
Fri, Oct 31 - Thu, Nov 6
Allegiant Air Logo
4:03 pm - 4:44 pmAVL-MDW
1h 41mnonstop
Allegiant Air Logo
5:23 pm - 8:00 pmMDW-AVL
1h 37mnonstop
$177Allegiant Air
Find Deal
Fri, Oct 10 - Mon, Oct 13
Allegiant Air Logo
4:03 pm - 4:44 pmAVL-MDW
1h 41mnonstop
Allegiant Air Logo
5:23 pm - 8:00 pmMDW-AVL
1h 37mnonstop
$184Allegiant Air
Find Deal
Fri, Oct 10 - Mon, Oct 13
Delta Logo
5:48 am - 9:48 amAVL-MDW
5h 00m1 stop
Delta Logo
6:00 am - 1:50 pmMDW-AVL
6h 50m1 stop
$227Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
5:59 pm - 9:36 pmAVL-MDW
4h 37m1 stop
Delta Logo
6:00 am - 11:36 amMDW-AVL
4h 36m1 stop
$229Delta
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Mon, Sep 22 - Mon, Sep 29
Delta Logo
5:59 pm - 9:36 pmAVL-MDW
4h 37m1 stop
Delta Logo
10:35 am - 3:20 pmMDW-AVL
3h 45m1 stop
$238Delta
Find Deal
Fri, Sep 26 - Tue, Sep 30

Allegiant Air flights from Asheville to Chicago Midway Airport

Our best Allegiant Air deals on Asheville to Chicago Midway Airport flight tickets
Allegiant Air
Sep 22
AVL11:21 amAsheville Regional
1h 39m
MDW12:00 pmChicago Midway
Sep 26
MDW5:33 pmChicago Midway
1h 37m
AVL8:10 pmAsheville Regional
$109
Find similar
Allegiant Air
Sep 26
AVL4:04 pmAsheville Regional
1h 39m
MDW4:43 pmChicago Midway
Sep 29
MDW12:50 pmChicago Midway
1h 37m
AVL3:27 pmAsheville Regional
$128
Find similar
Allegiant Air
Oct 10
AVL4:03 pmAsheville Regional
1h 41m
MDW4:44 pmChicago Midway
Oct 13
MDW5:23 pmChicago Midway
1h 37m
AVL8:00 pmAsheville Regional
$177
Find similar

Delta flights from Asheville to Chicago Midway Airport

Our best Delta deals on Asheville to Chicago Midway Airport flight tickets
Delta
Sep 27
AVL5:48 amAsheville Regional
5h 00m
1 stop
MDW9:48 amChicago Midway
Sep 30
MDW6:00 amChicago Midway
6h 50m
1 stop
AVL1:50 pmAsheville Regional
$227
Find similar
Delta
Sep 22
AVL5:59 pmAsheville Regional
4h 37m
1 stop
MDW9:36 pmChicago Midway
Sep 29
MDW6:00 amChicago Midway
4h 36m
1 stop
AVL11:36 amAsheville Regional
$229
Find similar
Delta
Sep 26
AVL5:59 pmAsheville Regional
4h 37m
1 stop
MDW9:36 pmChicago Midway
Sep 30
MDW10:35 amChicago Midway
3h 45m
1 stop
AVL3:20 pmAsheville Regional
$238
Find similar

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 August 25, 2025.
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

Mon 9/22

11:21 am-12:00 pm

Nonstop1h 39m

Chicago Midway

Fri 9/26

5:33 pm-8:10 pm

Nonstop1h 37m

$109

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 9/26

4:04 pm-4:43 pm

Nonstop1h 39m

Chicago Midway

Mon 9/29

12:50 pm-3:27 pm

Nonstop1h 37m

$128

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 10/31

4:21 pm-5:02 pm

Nonstop1h 41m

Chicago Midway

Sun 11/2

6:06 pm-8:25 am

1 stop13h 19m

$165

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Wed 10/29

6:06 pm-9:12 am

1 stop16h 06m

Chicago Midway

Fri 10/31

5:52 pm-8:29 pm

Nonstop1h 37m

$170

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 10/31

4:21 pm-5:02 pm

Nonstop1h 41m

Chicago Midway

Thu 11/6

3:40 pm-8:45 pm

1 stop28h 05m

$172

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 10/10

4:03 pm-4:44 pm

Nonstop1h 41m

Chicago Midway

Mon 10/13

5:23 pm-8:00 pm

Nonstop1h 37m

$177

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 10/10

4:03 pm-4:44 pm

Nonstop1h 41m

Chicago Midway

Mon 10/13

5:23 pm-8:00 pm

Nonstop1h 37m

$184

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Sat 9/27

5:48 am-9:48 am

1 stop5h 00m

Chicago Midway

Tue 9/30

6:00 am-1:50 pm

1 stop6h 50m

$227

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Mon 9/22

5:59 pm-9:36 pm

1 stop4h 37m

Chicago Midway

Mon 9/29

6:00 am-11:36 am

1 stop4h 36m

$229

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 9/26

5:59 pm-9:36 pm

1 stop4h 37m

Chicago Midway

Tue 9/30

10:35 am-3:20 pm

1 stop3h 45m

$238

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 month to fly to Chicago Midway Airport?

The month of July is, on average, the cheapest month to fly to Chicago Midway Airport from Asheville, with most prices found around $62. If you are unable to visit Chicago Midway Airport during the month of July, then departing from Asheville during the month September is also very affordable. Most momondo users find prices during this month for around $92.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Asheville. The lowest ticket price found for a Thursday departure recently was $60. 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 $122.

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 $93 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 are 1 cabin classes 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.

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

Best Price Found

$55

Fastest flight time

1h 39m

Direct flights

Tue, Thu and Sat
The best one-way flight to Chicago Midway Airport from Asheville in the past 72 hours is $55. The best round-trip flight deal from Asheville to Chicago Midway Airport found on momondo in the last 72 hours is $78.
The fastest flight from Asheville to Chicago Midway Airport takes 1h 39m
Direct flights go from Asheville to Chicago Midway Airport on Tuesday, Thursday and Saturday. The only airline offering direct flights is Allegiant Air.
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  • 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 1h 39m.

  • 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
702 reviews
Search Allegiant Air flights
DeltaPriceFrom $228Free CancellationRating
7.9
7,981 reviews
Search Delta flights

  • Allegiant Air Flights From Asheville to Chicago Midway Airport

    Allegiant Air flight deals from Asheville to Chicago Midway Airport start from $58 round-trip. Over the 1 Allegiant Air flight for this route in a normal week, average airfare is usually $108 round-trip - but some users have found much cheaper deals with momondo.

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 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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