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$49+ Cheap flights from Chicago (CHI) to Kentucky

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Chicago to Kentucky

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kentucky (USKY). 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 November 21, 2024.

Find flight deals from Chicago to Kentucky

Cheapest flights from Chicago to Kentucky
Explore the most affordable flight options available from Chicago to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/133:09 pmORD - BNA
Nonstop1h 37mFrontier
Sun 12/152:54 pmBNA - ORD
Nonstop1h 53mFrontier
Deal found 11/20$82
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/118:45 pmORD - BNA
Nonstop1h 40mAmerican Airlines
Mon 12/165:30 amBNA - ORD
Nonstop1h 54mAmerican Airlines
Deal found 11/20$97
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/117:30 pmMDW - BNA
Nonstop1h 30mSouthwest
Sat 12/144:15 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 11/20$98
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/127:25 amORD - BNA
Nonstop1h 46mUnited Airlines
Thu 12/196:00 amBNA - ORD
Nonstop2h 05mUnited Airlines
Deal found 11/20$117
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/106:37 pmORD - BNA
1 stop24h 23mMultiple Airlines
Wed 12/251:30 pmBNA - ORD
Nonstop1h 53mMultiple Airlines
Deal found 11/20$118
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/117:30 pmMDW - SDF
Nonstop1h 10mSouthwest
Thu 12/127:25 amSDF - MDW
Nonstop1h 20mSouthwest
Deal found 11/20$143
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/147:50 pmORD - SDF
Nonstop1h 36mUnited Airlines
Sun 12/157:00 amSDF - ORD
Nonstop1h 41mUnited Airlines
Deal found 11/20$147
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/156:40 pmORD - SDF
Nonstop1h 43mAmerican Airlines
Mon 12/164:00 pmSDF - ORD
Nonstop1h 34mAmerican Airlines
Deal found 11/20$157
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/223:14 pmMDW - TYS
Nonstop1h 27mAllegiant Air
Mon 11/251:50 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Deal found 11/20$160
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/113:10 pmORD - BNA
1 stop6h 35mSouthwest
Tue 12/178:10 pmBNA - ORD
Nonstop1h 50mSouthwest
Deal found 11/20$167
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/142:15 pmORD - TYS
Nonstop1h 50mUnited Airlines
Wed 12/185:46 pmTYS - ORD
Nonstop2h 09mUnited Airlines
Deal found 11/20$169
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/147:00 amORD - SDF
1 stop6h 27mDelta
Tue 12/177:08 amSDF - ORD
1 stop4h 41mDelta
Deal found 11/19$176

Find flights from Chicago to Kentucky within your budget

Customize your flight search to find flights from Chicago to Kentucky 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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/19

3:50 pm-5:29 pm

Nonstop1h 39m

Nashville Intl

Mon 2/24

2:23 pm-4:21 pm

Nonstop1h 58m

$60

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 12/11

8:45 pm-10:25 pm

Nonstop1h 40m

Nashville Intl

Mon 12/16

5:30 am-7:24 am

Nonstop1h 54m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 12/11

7:30 pm-9:00 pm

Nonstop1h 30m

Nashville Intl

Sat 12/14

4:15 pm-5:50 pm

Nonstop1h 35m

$98

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 1/3

5:45 pm-7:20 pm

Nonstop1h 35m

Nashville Intl

Mon 1/6

8:55 am-6:10 pm

1 stop9h 15m

$107

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 12/12

7:25 am-9:11 am

Nonstop1h 46m

Nashville Intl

Thu 12/19

6:00 am-8:05 am

Nonstop2h 05m

$117

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Tue 12/10

6:37 pm-7:00 pm

1 stop24h 23m

Nashville Intl

Wed 12/25

1:30 pm-3:23 pm

Nonstop1h 53m

$118

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 1/24

7:15 am-1:44 pm

1 stop6h 29m

Nashville Intl

Sun 1/26

5:43 pm-12:17 am

1 stop6h 34m

$126

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 1/14

5:55 pm-8:18 pm

Nonstop1h 23m

Louisville Intl

Sat 1/18

6:35 am-7:14 am

Nonstop1h 39m

$142

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 12/11

7:30 pm-9:40 pm

Nonstop1h 10m

Louisville Intl

Thu 12/12

7:25 am-7:45 am

Nonstop1h 20m

$143

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 12/14

7:50 pm-10:26 pm

Nonstop1h 36m

Louisville Intl

Sun 12/15

7:00 am-7:41 am

Nonstop1h 41m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Kentucky

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

Travel insights for flights from Chicago to Kentucky

Get recent, data-driven insights about flights from Chicago to Kentucky including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $298). Flying from Chicago to Kentucky in April is currently the most expensive (average of $370). 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 CHI to KY?

Find hourly flight availability from Chicago to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

When flying from Chicago to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Kentucky

Explore weekly flight availability from Chicago to Kentucky. 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 November 21, 2024.

The most flights from CHI to USKY are scheduled on a Wednesday (38 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (23 on average).

Rainfall in Kentucky by month

Plan your trip to Kentucky by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

Plan your trip to Kentucky by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kentucky, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated November 21, 2024.
To help decide which airline to fly from Chicago to Kentucky, see what other customers have to say about Frontier, American Airlines and Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,810 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

  • What are the cheapest airlines to fly from Chicago to Kentucky one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $49. However, be on the lookout for offers from Southwest and Frontier, as they are both options that can get you from Chicago to Kentucky for a low price.

  • What are the most popular routes from Chicago to Kentucky?

    The most popular route from Chicago to Kentucky is Chicago O'Hare Intl - Nashville Intl. You may also consider Chicago O'Hare Intl - Knoxville McGhee Tyson or Chicago O'Hare Intl - Cincinnati Cinci./N. Kentucky.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Kentucky on time: SkyWest Airlines (94%), ANA (93%), Envoy Air (92%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $72. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $50 on average our data indicates $299 when flying from Chicago to Kentucky.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $298). Flying from Chicago to Kentucky in April is currently the most expensive (average of $370). 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

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Alternative routes for Chicago to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Kentucky

Discover the top 4 airlines that operate flights from Chicago to Kentucky. 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$140FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$105Average$295FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$119Average$257FlexibilityNo cancel feeOn-time71%
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