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$141+ Cheap flights from Kingsport, TN 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
TYS — CHI
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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Find flight deals from Kingsport to Chicago

Cheapest flights from Kingsport to Chicago
Explore the most affordable flight options available from Kingsport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octobre 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/216:05 amTRI - MDW
1 stop4h 47mDelta
lun. 12/16:00 amMDW - TRI
1 stop5h 05mDelta
Deal found 10/29$269
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/2112:50 pmTRI - ORD
1 stop4h 56mDelta
lun. 12/15:23 amORD - TRI
1 stop5h 42mDelta
Deal found 10/28$269
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/126:05 amTRI - ORD
1 stop5h 32mDelta
dim. 11/165:23 amORD - TRI
1 stop5h 42mDelta
Deal found 10/27$279
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/137:32 pmTRI - MDW
1 stop5h 08mDelta
lun. 11/1710:47 amMDW - TRI
1 stop7h 00mDelta
Deal found 10/30$299
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/136:05 amTRI - ORD
1 stop7h 14mDelta
lun. 11/171:04 pmORD - TRI
1 stop4h 43mDelta
Deal found 10/28$299
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/134:13 pmTRI - ORD
1 stop8h 18mAmerican Airlines
lun. 11/173:50 pmORD - TRI
2 stops6h 37mAmerican Airlines
Deal found 10/30$304
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/216:25 amTRI - ORD
1 stop5h 17mAmerican Airlines
dim. 11/3012:52 amORD - TRI
1 stop6h 26mAmerican Airlines
Deal found 10/28$332
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/193:36 pmTRI - ORD
1 stop4h 47mDelta
jeu. 11/206:45 amORD - TRI
1 stop4h 20mDelta
Deal found 10/29$337
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/1912:50 pmTRI - MDW
1 stop4h 49mDelta
jeu. 11/2012:47 pmMDW - TRI
1 stop5h 00mDelta
Deal found 10/29$368
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/118:25 pmTRI - ORD
1 stop4h 21mAmerican Airlines
ven. 12/123:52 pmORD - TRI
2 stops6h 35mAmerican Airlines
Deal found 10/29$392
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/116:05 amTRI - MDW
1 stop6h 50mDelta
ven. 12/126:00 amMDW - TRI
1 stop5h 07mDelta
Deal found 10/29$398
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/14:10 pmTRI - MDW
1 stop7h 04mDelta
lun. 11/36:00 amMDW - TRI
1 stop5h 43mDelta
Deal found 10/29$424

Cheap flight deals from Kingsport to Chicago

Keep the following information in mind while searching for Kingsport to Chicago flight deals. Data was last updated octobre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Delta)

One-way from

$141
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$380
Provider with most accurate pricing for Blountville Tri Cities TN/VA-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Blountville Tri Cities TN/VA-Chicago (CHI) flights.
Search Deals
From Kingsport to Chicago (CHI)
Search Deals
One-way flight from Kingsport to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kingsport 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 octobre 30, 2025.
Use the filters below to find and compare flights from Kingsport to Chicago that are best for you.

Fly from

Kingsport

Fly to

Chicago

Route

Depart

Return

Price

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

ven. 11/21

6:05 am-9:52 am

1 stop4h 47m

Chicago Midway

lun. 12/1

6:00 am-12:05 pm

1 stop5h 05m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

ven. 1/23

10:17 am-1:39 pm

1 stop4h 22m

Chicago O'Hare Intl

ven. 1/30

5:33 am-12:26 pm

1 stop5h 53m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

jeu. 1/8

1:42 pm-4:43 pm

1 stop4h 01m

Chicago O'Hare Intl

mer. 1/14

7:05 am-1:02 pm

1 stop4h 57m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

ven. 11/21

12:50 pm-4:46 pm

1 stop4h 56m

Chicago O'Hare Intl

lun. 12/1

5:23 am-12:05 pm

1 stop5h 42m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

jeu. 1/22

3:18 pm-6:49 pm

1 stop4h 31m

Chicago O'Hare Intl

ven. 1/30

5:33 am-12:26 pm

1 stop5h 53m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

mar. 1/27

3:18 pm-7:21 pm

1 stop5h 03m

Chicago O'Hare Intl

lun. 2/2

7:05 am-12:26 pm

1 stop4h 21m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

mer. 1/7

1:42 pm-4:44 pm

1 stop4h 02m

Chicago O'Hare Intl

mar. 1/13

7:05 am-1:02 pm

1 stop4h 57m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

dim. 1/25

3:18 pm-6:49 pm

1 stop4h 31m

Chicago O'Hare Intl

sam. 1/31

7:05 am-12:26 pm

1 stop4h 21m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

mer. 1/14

1:42 pm-4:44 pm

1 stop4h 02m

Chicago O'Hare Intl

mer. 1/21

7:05 am-12:26 pm

1 stop4h 21m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

mar. 1/6

1:42 pm-4:43 pm

1 stop4h 01m

Chicago O'Hare Intl

mer. 1/14

7:05 am-1:02 pm

1 stop4h 57m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 25 results
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Best time to book a flight from Kingsport to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kingsport 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 Kingsport to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Kingsport to Chicago (average of $58). Flying from Kingsport to Chicago in February is currently the most expensive (average of $189). 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 K1N to CHI?

Find hourly flight availability from Kingsport 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 octobre 30, 2025.

It’s optimal to fly from Kingsport to Chicago in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Kingsport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kingsport to Chicago. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Kingsport to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Kingsport 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 octobre 30, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Kingsport 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.
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

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

  • How long is the flight from Kingsport to Chicago?

    There are many flights that can get you from Kingsport to Chicago in 4h 47m. Fly via Delta to get the fastest option. There are 465 mi between Kingsport and Chicago.

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

    Before booking your flight to Chicago from Kingsport, check out the most reliable airlines to get you to your destination on time: Republic Airways (96%), Avianca (92%), GoJet( 91%).

  • What are the cheapest flights from Kingsport to Chicago?

    Looking at all options, your cheapest flight can be booked for $134. While the most popular route (Blountville Tri Cities TN/VA - Chicago O'Hare Intl) can be booked for $269 on average, our data indicates $935 when flying from Kingsport to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kingsport 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 Kingsport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Kingsport to Chicago (average of $58). Flying from Kingsport to Chicago in February is currently the most expensive (average of $189). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Kingsport to Chicago

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Top 4 airlines flying from Kingsport to Chicago

Discover the top 4 airlines that operate flights from Kingsport 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 octobre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$58Average$97FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$189Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$289FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$333FlexibilityNo cancel feeOn-timeN/A

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