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$51+ Cheap flights from Asheville (AVL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
AVL — CHI
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
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Cheapflights Tip: The best prices from Asheville Regional to Chicago are usually found in October or August, booked 85 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap flight deals from Asheville to Chicago

Cheapest flights from Asheville to Chicago
Explore the most affordable flight options available from Asheville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:53 pm
AVL
-
ORD
1 stop17h 34m
Multiple Airlines
Mon 5/115:05 am
ORD
-
AVL
1 stop16h 14m
Multiple Airlines
Deal found 4/16$204
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:53 pm
AVL
-
ORD
1 stop17h 34m
Multiple Airlines
Tue 5/123:55 pm
ORD
-
AVL
1 stop18h 59m
Multiple Airlines
Deal found 4/16$205
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:35 pm
AVL
-
ORD
1 stop7h 49m
Multiple Airlines
Mon 5/41:27 pm
ORD
-
AVL
1 stop7h 52m
Multiple Airlines
Deal found 4/17$206
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:30 am
AVL
-
MDW
2 stops37h 56m
Multiple Airlines
Sun 5/38:39 am
MDW
-
AVL
1 stop6h 47m
Multiple Airlines
Deal found 4/17$208
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:57 pm
AVL
-
ORD
1 stop11h 41m
Multiple Airlines
Sun 5/106:50 am
ORD
-
AVL
2 stops15h 26m
Multiple Airlines
Deal found 4/16$208
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:26 pm
AVL
-
MDW
1 stop26h 07m
Allegiant Air
Mon 6/158:20 pm
MDW
-
AVL
Nonstop1h 39m
Allegiant Air
Deal found 4/17$209
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:14 pm
AVL
-
ORD
1 stop12h 45m
Multiple Airlines
Sun 5/103:44 pm
ORD
-
AVL
1 stop29h 35m
Multiple Airlines
Deal found 4/17$211
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:15 am
AVL
-
ORD
2 stops14h 24m
Multiple Airlines
Mon 5/41:27 pm
ORD
-
AVL
1 stop7h 52m
Multiple Airlines
Deal found 4/17$212
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:57 pm
AVL
-
ORD
1 stop11h 41m
Multiple Airlines
Fri 5/86:55 am
ORD
-
AVL
2 stops14h 24m
Multiple Airlines
Deal found 4/16$215
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:30 am
AVL
-
MDW
2 stops39h 32m
Multiple Airlines
Fri 5/224:28 pm
MDW
-
AVL
Nonstop1h 34m
Multiple Airlines
Deal found 4/19$216
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:57 pm
AVL
-
ORD
1 stop11h 41m
Multiple Airlines
Sat 5/168:30 am
ORD
-
AVL
1 stop9h 18m
Multiple Airlines
Deal found 4/20$217
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:15 am
AVL
-
MDW
2 stops14h 11m
Multiple Airlines
Sun 5/38:39 am
MDW
-
AVL
1 stop6h 47m
Multiple Airlines
Deal found 4/17$220

Find flight deals from Asheville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Asheville (AVL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$204
(Kiwi.com)

One-way from

$51
(Cheapflightsfares)

Popular in

January

Cheapest in

October

Average price

$299

Good round-trip deal

$138 or less

Good one-way deal

$279 or less
Provider with most accurate pricing for Asheville Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Asheville Regional-Chicago (CHI) flights.
Search Deals
From Asheville Regional to Chicago (CHI)
Search Deals
One-way flight from Asheville Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Asheville Regional to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Asheville Regional to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Asheville to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated April 21, 2026.
Use the filters below to find and compare flights from Asheville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AshevilleChicago

AVL - ORD

AVLORD

Asheville Regional

Mon 5/18

6:45 am-8:00 am

Nonstop2h 15m

Chicago O'Hare Intl

Mon 5/25

5:55 pm-9:00 pm

Nonstop2h 05m

$269

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Tue 6/16

5:35 am-10:07 am

1 stop5h 32m

Chicago Midway

Sat 6/20

6:05 am-11:10 am

1 stop4h 05m

$287

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Sat 6/13

11:56 am-3:40 pm

1 stop4h 44m

Chicago Midway

Tue 6/16

6:05 am-11:10 am

1 stop4h 05m

$287

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Sat 8/1

1:14 pm-5:52 pm

1 stop5h 38m

Chicago Midway

Sat 8/8

4:22 pm-11:46 pm

1 stop6h 24m

$287

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Wed 9/2

6:15 pm-9:46 pm

1 stop4h 31m

Chicago Midway

Sat 9/5

6:00 am-10:42 am

1 stop3h 42m

$287

AshevilleChicago

AVL - ORD

AVLORD

Asheville Regional

Wed 9/2

7:45 am-12:08 pm

1 stop5h 23m

Chicago O'Hare Intl

Sat 9/5

5:30 am-10:42 am

1 stop4h 12m

$287

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Thu 8/13

5:40 am-9:50 am

1 stop5h 10m

Chicago Midway

Sat 8/15

6:00 am-10:42 am

1 stop3h 42m

$288

AshevilleChicago

AVL - MDW

AVLMDW

Asheville Regional

Fri 7/10

1:14 pm-6:18 pm

1 stop6h 04m

Chicago Midway

Tue 7/14

6:05 am-11:08 am

1 stop4h 03m

$288

AshevilleChicago

AVL - ORD

AVLORD

Asheville Regional

Fri 7/24

5:04 pm-10:08 pm

1 stop6h 04m

Chicago O'Hare Intl

Tue 7/28

1:44 pm-8:51 pm

1 stop6h 07m

$288

AshevilleChicago

AVL - ORD

AVLORD

Asheville Regional

Fri 9/4

3:50 pm-9:20 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 9/8

7:10 am-1:31 pm

1 stop5h 21m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/18

Showing 1-10 of 37 resultsSorted by cheapest first
1
2
3
4

Compare providers for flights from Asheville to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Asheville to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Asheville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Asheville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Asheville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Asheville-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Asheville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Asheville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Asheville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Asheville to Chicago

How far ahead should I book a flight from Asheville to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Asheville to Chicago. Price data was last updated on April 17, 2026.

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Asheville to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Asheville to Chicago?

Currently, August is the cheapest month in which you can book a flight from Asheville to Chicago (average of $58). Flying from Asheville to Chicago in January is currently the most expensive (average of $209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from AVL to CHI?

Find hourly flight availability from Asheville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 21, 2026.

One of the essential ways to save on airfare from Asheville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 17% on airfare.

Weekly flight availability from Asheville to Chicago

Explore weekly flight availability from Asheville to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 21, 2026.

The most flights from AVL to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Asheville to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 21, 2026.
Peruse reviews from past customers who have flown with United Airlines,Allegiant Air, andAmerican Airlines from Asheville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,613 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,613 reviews
United Airlines
7.4
Good
9,613 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Allegiant Air
7.3
Good
706 reviews
United Airlines
7.4
Good
9,613 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,645 reviews
United Airlines
7.4
Good
9,613 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Asheville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Asheville to Chicago?

    If you book a flight to Chicago from Asheville, you will be flying from Asheville Regional, which is the city’s only airport. Asheville Regional (AVL) is located 10.9 mi from the center of Asheville. There are 11 flights from Asheville Regional to Chicago per day from 3 different airlines.

  • How long is the flight from Asheville to Chicago?

    There are many flights that can get you from Asheville to Chicago in 2h 15m. Fly via United Airlines or Delta to get the fastest option. Asheville and Chicago are separated by a distance of 536 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Asheville to Chicago round-trip?

    Flying on Allegiant Air is currently your cheapest option to Chicago, with prices starting at $58. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $207 and $208, respectively. You may be able to fly from Asheville to Chicago for 79% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Asheville to Chicago?

    The top 3 most reliable airlines when flying from Asheville to Chicago are Envoy Air (69%), American Airlines (68%) and Republic Airways (63%).

  • What are the cheapest flights from Asheville to Chicago?

    Looking at all options, your cheapest flight can be booked for $173. While the most popular route (Asheville Regional - Chicago O'Hare Intl) can be booked for $177 on average, our data indicates $1,190 when flying from Asheville to Chicago.

  • Can I find deals for flights from Asheville to Chicago that include hotel bookings?

    Yes. In addition to deals on Asheville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Asheville to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Asheville to Chicago.

  • Can I find deals for business class flights from Asheville to Chicago?

    Yes. Cheapflights offers flight deals from Asheville to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Asheville to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Asheville to Chicago (average of $58). Flying from Asheville to Chicago in January is currently the most expensive (average of $209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 3 airlines flying from Asheville to Chicago

Discover the top 3 airlines that operate flights from Asheville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$58Average$91FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$207Average$275FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$208Average$307FlexibilityNo cancel feeOn-time69%

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