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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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
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 December 22, 2024.

Round-trip from

$75
(Gotogate)

One-way from

$49
(Frontier)
From Chicago (CHI) to Kentucky
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One-way flight from Chicago (CHI) to Kentucky
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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 December 22, 2024.

This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/252:45 pmORD - BNA
Nonstop1h 37mFrontier
Wed 1/11:30 pmBNA - ORD
Nonstop1h 53mFrontier
Deal found 12/21$207
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:51 pmMDW - BNA
1 stop3h 34mDelta
Mon 1/66:15 amBNA - MDW
1 stop6h 53mDelta
Deal found 12/20$226
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:30 pmORD - SDF
1 stop3h 57mDelta
Wed 1/11:30 pmSDF - ORD
1 stop4h 10mDelta
Deal found 12/21$244
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/313:47 pmORD - BNA
Nonstop1h 37mAmerican Airlines
Wed 1/15:30 amBNA - ORD
Nonstop1h 55mAmerican Airlines
Deal found 12/21$247
This Southwest deal was found by Cheapflights users on 12/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:30 pmMDW - BNA
Nonstop1h 30mSouthwest
Wed 1/17:30 amBNA - MDW
Nonstop1h 35mSouthwest
Deal found 12/19$248
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:51 pmMDW - CVG
1 stop4h 03mDelta
Wed 1/16:00 amCVG - MDW
1 stop3h 50mDelta
Deal found 12/21$258
This Southwest deal was found by Cheapflights users on 12/21. 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.
Tue 12/316:30 pmMDW - CVG
Nonstop1h 10mSouthwest
Wed 1/17:25 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 12/21$270
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/316:05 pmORD - SDF
Nonstop1h 32mUnited Airlines
Wed 1/18:28 amSDF - ORD
Nonstop1h 45mUnited Airlines
Deal found 12/21$285
This FlightHub deal was found by Cheapflights users on 12/21. 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 12/244:08 pmMDW - CVG
1 stop17h 26mFrontier
Mon 12/304:50 pmCVG - MDW
1 stop7h 24mFrontier
Deal found 12/21$290
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/294:05 pmORD - TYS
1 stop4h 37mAmerican Airlines
Wed 1/15:53 amTYS - ORD
1 stop6h 09mAmerican Airlines
Deal found 12/22$298
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:30 pmORD - BNA
1 stop23h 26mMultiple Airlines
Wed 1/11:30 pmBNA - ORD
Nonstop1h 53mMultiple Airlines
Deal found 12/21$306
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:30 pmORD - BNA
1 stop3h 55mDelta
Fri 1/310:36 amBNA - ORD
1 stop6h 04mDelta
Deal found 12/20$323

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 2,558,603 searches. Data last updated December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 2/7

3:09 pm-4:48 pm

Nonstop1h 39m

Nashville Intl

Sun 2/9

2:44 pm-4:42 pm

Nonstop1h 58m

$75

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/19

3:14 pm-9:55 pm

1 stop6h 41m

Nashville Intl

Wed 2/26

6:29 pm-8:27 pm

Nonstop1h 58m

$112

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 2/24

6:40 am-1:23 pm

1 stop6h 43m

Nashville Intl

Fri 2/28

6:01 pm-12:17 am

1 stop6h 16m

$116

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 1/29

2:12 pm-3:48 pm

Nonstop1h 36m

Nashville Intl

Sat 2/1

5:00 pm-6:49 pm

Nonstop1h 49m

$138

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 2/4

2:55 pm-5:19 pm

Nonstop1h 24m

Louisville Intl

Tue 2/11

6:23 pm-7:00 pm

Nonstop1h 37m

$138

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 1/18

2:12 pm-4:00 pm

Nonstop1h 48m

Nashville Intl

Sat 1/25

12:05 pm-1:56 pm

Nonstop1h 51m

$149

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 2/24

4:20 pm-5:50 pm

Nonstop1h 30m

Nashville Intl

Fri 2/28

9:40 am-11:15 am

Nonstop1h 35m

$158

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 1/18

2:40 pm-5:06 pm

Nonstop1h 26m

Louisville Intl

Sat 1/25

10:35 am-11:10 am

Nonstop1h 35m

$167

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 1/18

3:56 pm-10:52 pm

1 stop6h 56m

Nashville Intl

Sat 1/25

9:29 am-8:13 pm

1 stop10h 44m

$175

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/19

7:05 am-1:02 pm

1 stop5h 57m

Nashville Intl

Wed 2/26

11:20 am-3:43 pm

1 stop4h 23m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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 December 22, 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 December 22, 2024.

The most flights from CHI to USKY are scheduled on a Saturday (35 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 December 22, 2024.
To help decide which airline to fly from Chicago to Kentucky, see what other customers have to say about Delta, Southwest and Frontier. 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
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
823 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, with whom users have recently found tickets for as low as $49. However, be on the lookout for offers from United Airlines and Southwest, 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: Republic Airways (91%), Air Wisconsin (91%), American Airlines (90%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $82 on average our data indicates $323 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 $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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.

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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 2,558,603 searches. Data last updated December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$140FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$105Average$295FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$118Average$260FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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