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$169+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
TYS — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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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 August 18, 2025.

Round-trip from

$269
(Delta)

One-way from

$169
(American Airlines)

Popular in

May

Cheapest in

November

Average price

$442
From Kingsport to Chicago (CHI)
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One-way flight from Kingsport to Chicago (CHI)
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Highest demand for flights based on searches. 26% potential increase in price ($144 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($45 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 18, 2025.

This Delta deal was found by Cheapflights users on 8/18. 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.
Wed 10/157:17 pmTRI - MDW
1 stop3h 57mDelta
Wed 10/226:00 amMDW - TRI
1 stop5h 43mDelta
Deal found 8/18$269
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:25 pmTRI - ORD
1 stop6h 47mAmerican Airlines
Sun 10/55:00 amORD - TRI
1 stop4h 47mAmerican Airlines
Deal found 8/17$269
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:13 amTRI - ORD
1 stop4h 17mAmerican Airlines
Sun 9/75:00 amORD - TRI
1 stop4h 47mAmerican Airlines
Deal found 8/17$274
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/27:22 pmTRI - ORD
1 stop4h 37mAmerican Airlines
Sat 9/65:00 amORD - TRI
1 stop3h 53mAmerican Airlines
Deal found 8/18$279
This Delta deal was found by Cheapflights users on 8/17. 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.
Fri 11/213:50 pmTRI - MDW
1 stop6h 54mDelta
Mon 12/16:00 amMDW - TRI
1 stop5h 05mDelta
Deal found 8/17$288
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 10/178:08 pmTRI - ORD
1 stop4h 45mAmerican Airlines
Sun 10/195:22 amORD - TRI
1 stop4h 23mAmerican Airlines
Deal found 8/18$288
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/186:05 amTRI - ORD
2 stops6h 01mAmerican Airlines
Sun 10/195:22 amORD - TRI
1 stop4h 23mAmerican Airlines
Deal found 8/18$293
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/42:50 pmTRI - ORD
1 stop4h 44mAmerican Airlines
Sat 10/115:20 amORD - TRI
1 stop4h 25mAmerican Airlines
Deal found 8/17$294
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sun 8/316:30 amTRI - ORD
1 stop5h 13mAmerican Airlines
Sun 9/75:00 amORD - TRI
1 stop4h 47mAmerican Airlines
Deal found 8/16$303
This Delta deal was found by Cheapflights users on 8/18. 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.
Tue 9/210:57 amTRI - MDW
1 stop3h 39mDelta
Sat 9/66:00 amMDW - TRI
1 stop5h 41mDelta
Deal found 8/18$304
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:12 pmTRI - ORD
1 stop6h 41mAmerican Airlines
Sun 10/125:22 amORD - TRI
1 stop4h 23mAmerican Airlines
Deal found 8/17$307
This Delta deal was found by Cheapflights users on 8/18. 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.
Wed 10/156:10 amTRI - ORD
1 stop7h 06mDelta
Tue 10/2110:30 amORD - TRI
2 stops10h 51mDelta
Deal found 8/18$313

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 August 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

Wed 10/15

7:17 pm-10:14 pm

1 stop3h 57m

Chicago Midway

Tue 10/21

6:00 am-12:43 pm

1 stop5h 43m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Fri 9/12

5:25 pm-11:12 pm

1 stop6h 47m

Chicago O'Hare Intl

Mon 9/15

5:00 am-9:53 am

1 stop3h 53m

$269

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Wed 10/15

7:17 pm-10:14 pm

1 stop3h 57m

Chicago Midway

Wed 10/22

6:00 am-12:43 pm

1 stop5h 43m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Mon 9/22

4:31 pm-11:17 pm

1 stop7h 46m

Chicago O'Hare Intl

Sat 9/27

5:00 am-9:53 am

1 stop3h 53m

$269

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Wed 10/15

7:17 pm-10:14 pm

1 stop3h 57m

Chicago Midway

Sat 10/18

6:00 am-12:43 pm

1 stop5h 43m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Mon 9/15

7:02 pm-11:12 pm

1 stop5h 10m

Chicago O'Hare Intl

Mon 9/22

7:02 am-2:25 pm

1 stop6h 23m

$269

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Sat 10/18

4:10 pm-10:14 pm

1 stop7h 04m

Chicago Midway

Tue 10/21

6:00 am-12:43 pm

1 stop5h 43m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 9/18

8:12 pm-11:39 pm

1 stop4h 27m

Chicago O'Hare Intl

Sun 9/21

5:00 am-10:47 am

1 stop4h 47m

$269

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Sat 10/18

4:10 pm-10:14 pm

1 stop7h 04m

Chicago Midway

Wed 10/22

6:00 am-12:43 pm

1 stop5h 43m

$269

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 10/16

8:08 pm-11:53 pm

1 stop4h 45m

Chicago O'Hare Intl

Sat 10/18

5:20 am-10:45 am

1 stop4h 25m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 26 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 $245). Flying from Kingsport to Chicago in March is currently the most expensive (average of $321). 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 August 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kingsport to Chicago as you normally would.

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 August 17, 2025.

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

Weekly flight availability from Kingsport to Chicago

Explore weekly flight availability from Kingsport 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 August 18, 2025.

The most flights from K1N to CHI are scheduled on a Monday (34 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 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 August 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
8.0
Very good
7,981 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 57m. 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: Avianca (93%), Envoy Air (89%), Republic Airways( 86%).

  • What are the cheapest flights from Kingsport to Chicago?

    Looking at all options, your cheapest flight can be booked for $180. While the most popular route (Blountville Tri Cities TN/VA - Chicago O'Hare Intl) can be booked for $269 on average our data indicates $1,137 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 $245). Flying from Kingsport to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$58Average$97FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$179Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$318FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$365FlexibilityNo cancel feeOn-timeN/A

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