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$269+ Cheap flights from Kingsport, TN to Chicago (CHI)

This is the cheapest round-trip 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
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:26 pmTRI - ORD
1 stop4h 33mAmerican Airlines
Sat 12/276:38 pmORD - TRI
1 stop4h 21mAmerican Airlines
Deal found 12/16$374
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:53 pmTRI - ORD
1 stop6h 09mDelta
Sat 12/276:45 amORD - TRI
1 stop5h 24mDelta
Deal found 12/17$534
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:53 pmTRI - MDW
1 stop4h 29mDelta
Sat 12/274:25 pmMDW - TRI
1 stop5h 24mDelta
Deal found 12/17$694

Find flight deals from Kingsport to Chicago

Keep the following information in mind while searching for Kingsport to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Delta)

Popular in

May

Cheapest in

September

Average price

$298
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
Highest demand for flights based on searches. 28% potential increase in price ($152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 18, 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

Fri 1/16

1:45 pm-4:29 pm

1 stop3h 44m

Chicago Midway

Fri 1/23

6:00 am-12:26 pm

1 stop5h 26m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Fri 1/16

4:33 pm-10:18 pm

1 stop6h 45m

Chicago O'Hare Intl

Fri 1/23

8:12 am-3:06 pm

1 stop5h 54m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 1/1

8:26 pm-11:42 pm

1 stop4h 16m

Chicago O'Hare Intl

Mon 1/5

7:36 am-3:43 pm

1 stop7h 07m

$329

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Fri 5/22

8:38 pm-11:57 pm

1 stop4h 19m

Chicago O'Hare Intl

Mon 5/25

5:29 am-10:14 am

1 stop3h 45m

$439

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Mon 5/4

6:55 pm-11:55 pm

1 stop6h 00m

Chicago O'Hare Intl

Fri 5/8

7:10 am-12:06 pm

1 stop3h 56m

$468

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Mon 5/4

8:34 pm-11:50 pm

1 stop4h 16m

Chicago O'Hare Intl

Fri 5/8

4:45 pm-11:44 pm

1 stop5h 59m

$577

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Thu 1/1

6:00 am-9:05 am

1 stop4h 05m

Chicago Midway

Mon 1/5

6:45 am-2:21 pm

1 stop6h 36m

$799

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December 18, 2025.

It’s optimal to fly from Kingsport to Chicago in the afternoon. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight at noon.

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 December 13, 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 December 18, 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
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 3h 44m. Fly via Delta or American Airlines to get the fastest option. There are 465 mi between Kingsport and Chicago. This flight may include one or multiple stops.

  • 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 (100%), ANA (74%), United Airlines( 70%).

  • What are the cheapest flights from Kingsport to Chicago?

    Looking at all options, your cheapest flight can be booked for $162. While the most popular route (Blountville Tri Cities TN/VA - Chicago O'Hare Intl) can be booked for $269 on average, our data indicates $979 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$58Average$94FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$189Average$324FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$290FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$333FlexibilityNo cancel feeOn-timeN/A

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