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$88+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
TYS — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 am
TRI
-
ORD
Nonstop2h 00m
United Airlines
Tue 6/239:15 pm
ORD
-
TRI
Nonstop1h 44m
United Airlines
Deal found 1/27$189
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
TRI
-
ORD
Nonstop2h 00m
United Airlines
Sat 7/259:15 pm
ORD
-
TRI
Nonstop1h 44m
United Airlines
Deal found 1/28$204
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 4/177:15 pm
TRI
-
MDW
1 stop4h 13m
Delta
Mon 4/2010:43 am
MDW
-
TRI
1 stop6h 52m
Delta
Deal found 1/28$209
This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 2/187:13 pm
TRI
-
ORD
1 stop5h 43m
Delta
Sun 2/226:45 am
ORD
-
TRI
1 stop4h 37m
Delta
Deal found 1/27$209
This Delta deal was found by Cheapflights users on 1/26. 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 2/111:11 pm
TRI
-
MDW
1 stop5h 18m
Delta
Sun 2/156:00 am
MDW
-
TRI
1 stop5h 22m
Delta
Deal found 1/26$239
This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 2/111:11 pm
TRI
-
ORD
1 stop7h 10m
Delta
Sun 2/155:25 am
ORD
-
TRI
1 stop5h 57m
Delta
Deal found 1/27$239
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
TRI
-
ORD
Nonstop2h 00m
United Airlines
Mon 7/69:15 pm
ORD
-
TRI
Nonstop1h 44m
United Airlines
Deal found 1/28$244
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 7/223:50 pm
TRI
-
MDW
1 stop6h 56m
Delta
Sat 7/256:00 am
MDW
-
TRI
1 stop5h 06m
Delta
Deal found 1/28$249
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 7/226:55 pm
TRI
-
ORD
1 stop6h 02m
Delta
Sat 7/256:00 am
ORD
-
TRI
1 stop5h 06m
Delta
Deal found 1/28$253
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 2/51:11 pm
TRI
-
MDW
1 stop5h 18m
Delta
Mon 2/96:00 am
MDW
-
TRI
1 stop5h 26m
Delta
Deal found 1/26$269
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 2/51:11 pm
TRI
-
ORD
1 stop6h 38m
Delta
Mon 2/95:30 am
ORD
-
TRI
1 stop5h 56m
Delta
Deal found 1/26$269
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/123:33 pm
TRI
-
ORD
1 stop17h 44m
Multiple Airlines
Thu 4/1612:25 pm
ORD
-
TRI
1 stop27h 03m
Multiple Airlines
Deal found 1/28$272

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$88
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$269
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. 31% potential increase in price ($169 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 - ORD

TRIORD

Blountville Tri Cities TN/VA

Sat 6/20

6:00 am-7:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Tue 6/23

9:15 pm-11:59 pm

Nonstop1h 44m

$189

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Wed 7/22

6:00 am-7:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Sat 7/25

9:15 pm-11:59 pm

Nonstop1h 44m

$204

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Fri 4/17

7:15 pm-10:28 pm

1 stop4h 13m

Chicago Midway

Mon 4/20

10:43 am-6:35 pm

1 stop6h 52m

$209

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 4/16

4:04 pm-9:25 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 4/20

7:14 am-3:22 pm

1 stop7h 08m

$209

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Fri 4/17

4:04 pm-8:16 pm

1 stop5h 12m

Chicago O'Hare Intl

Mon 4/20

8:15 am-3:22 pm

1 stop6h 07m

$209

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Wed 2/18

7:13 pm-11:56 pm

1 stop5h 43m

Chicago O'Hare Intl

Sun 2/22

6:45 am-12:22 pm

1 stop4h 37m

$209

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Wed 2/11

1:11 pm-5:29 pm

1 stop5h 18m

Chicago Midway

Sun 2/15

6:00 am-12:22 pm

1 stop5h 22m

$239

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 2/12

3:33 pm-6:49 pm

1 stop4h 16m

Chicago O'Hare Intl

Mon 2/16

6:45 am-2:48 pm

1 stop7h 03m

$239

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Wed 2/11

1:11 pm-7:21 pm

1 stop7h 10m

Chicago O'Hare Intl

Sun 2/15

5:25 am-12:22 pm

1 stop5h 57m

$239

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Wed 7/22

3:50 pm-9:46 pm

1 stop6h 56m

Chicago Midway

Sat 7/25

6:00 am-12:06 pm

1 stop5h 06m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 27 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 January 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 January 29, 2026.

It’s optimal to fly from Kingsport to Chicago in the afternoon. By choosing this option you can save up to 32% 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 January 24, 2026.

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.

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 January 29, 2026.

The most flights from K1N to CHI are scheduled on a Thursday (24 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

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 January 29, 2026.
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
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

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
8,128 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

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
11,205 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

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 2h. Fly via United Airlines or Delta to get the fastest option. There are 480 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 (79%), Envoy Air (75%), ANA( 73%).

  • What are the cheapest flights from Kingsport to Chicago?

    Looking at all options, your cheapest flight can be booked for $138. While the most popular route (Blountville Tri Cities TN/VA - Chicago O'Hare Intl) can be booked for $189 on average, our data indicates $1,013 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 January 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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Alternative routes for Kingsport to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$58Average$94FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$189Average$320FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$294FlexibilityNo cancel feeOn-time71%
DeltaCheapest$233Average$387FlexibilityNo cancel feeOn-timeN/A

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