Cheap flights from Chicago (CHI) to Kentucky from $56

This is the cheapest one-way flight price, found on 9/27. Prices may vary by date and flight preferences.
CHI — SDF
Oct 3 — Oct 101

How far in advance should I book a flight from Chicago to Kentucky?

Find a great deal and save up to 43% by booking at least 54 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Kentucky within the next two weeks, with the cheapest ticket starting at $364.

What is the cheapest month to fly from Chicago to Kentucky?

January is one of the best times of the year to fly to Kentucky from Chicago. Prices for January average $323 per person but you can even find prices for as low as $131. The most expensive prices can be found in the month of June. Opting for a January flight can save you 38% on your journey compared to booking in June

When is the cheapest time to fly from Chicago to Kentucky (CHI - KY)?

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.

Cheap Spirit Airlines flights from Chicago to Kentucky

Peruse some of the lowest-priced Spirit Airlines flights we've found from Chicago to Kentucky. Come back soon if you're not finding the exact deal you're looking for.

Cheap Delta flights from Chicago to Kentucky

To aid your search, here are some of the cheapest Delta flights we've found from Chicago to Kentucky. Deals frequently update to provide users with more options.

Cheap Chicago to Kentucky flights in September & October 2023

The best prices found for CHI to Kentucky flights for September, October
The lowest fares we've come across on flights traveling from Chicago to Kentucky in September and October 2023. More deals are always being added, so be sure to check back regularly.

Chicago to Kentucky 2023 flight deals

Cheap flights to Kentucky from Chicago found for this year
The lowest fares we've come across on flights traveling from Chicago to Kentucky in September and October 2023. More deals are always being added, so be sure to check back regularly.

Non-stop flights to Kentucky from Chicago

Save time with Chicago to Kentucky direct flight deals
If you're seeking options on non-stop flights from Chicago to Kentucky, check out these fares. Users seeking other options on flights from Chicago to Kentucky should update the search form at the top of the page.

Chicago to Kentucky flights leaving soon

Late deals on return flights to Kentucky from Chicago, departing today and this week
Consider one of these great deals we found on last-minute flights from Chicago to Kentucky. Tip: verify your flight details before completing your reservation.

One-way flights to Kentucky from Chicago

The cheapest one-way flights from Chicago to Kentucky
Take a look at some of the one-way flights we've detected from Chicago to Kentucky. For those needing a return trip from Chicago, there is a search form available above.

Find flights from Chicago to Kentucky within your budget

Use the slider to find flights from Chicago to Kentucky that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$121 - $177

Route

Depart

Return

Price

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 10/24

1 stop14h 59m

Louisville Intl

Thu 10/26

1 stop7h 13m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Thu 10/26

1 stop13h 42m

Louisville Intl

Sat 10/28

1 stop13h 28m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 11/8

Nonstop1h 27m

Louisville Intl

Sun 11/12

Nonstop1h 32m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sun 10/22

1 stop13h 42m

Louisville Intl

Wed 10/25

1 stop8h 32m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Fri 11/3

1 stop13h 42m

Louisville Intl

Sun 11/5

1 stop13h 22m

Chicago O'Hare IntlOwensboro Daviess County

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 12/11

Nonstop1h 30m

Owensboro Daviess County

Wed 12/13

Nonstop1h 35m

Chicago O'Hare IntlLexington Blue Grass

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 12/5

Nonstop1h 25m

Lexington Blue Grass

Wed 12/6

Nonstop1h 45m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 11/7

1 stop5h 01m

Louisville Intl

Wed 11/8

Nonstop1h 35m

Chicago O'Hare IntlLouisville Intl

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Fri 11/10

1 stop4h 50m

Louisville Intl

Sun 11/12

1 stop4h 25m

Flights are sorted by cheapest first

Deals found on 9/28

Reviews of airlines servicing Kentucky

To help decide which airline to fly from Chicago to Kentucky, see what other customers have to say about Spirit Airlines, Delta and United Airlines. 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
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

Delta
7.9
Good
3,023 reviews
Delta
7.9
Good
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

Allegiant Air
7.5
Good
103 reviews
Delta
7.9
Good
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

United Airlines
7.4
Good
1,890 reviews
Delta
7.9
Good
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

American Airlines
7.2
Good
2,635 reviews
Delta
7.9
Good
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

Spirit Airlines
6.3
Okay
1,483 reviews
Delta
7.9
Good
3,023 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.2

Boarding

8.0

Entertainment

7.8

Reviews

1 / 10

Most importantly it was on time, then great crew, great service and comfortable.

Related info for your journey

Useful info, stats and facts about Chicago to Kentucky flights.

Can I find flights from Chicago to Kentucky for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Kentucky for under $200. The cheapest flight booked recently is on Spirit Airlines for just $121, but on average you can expect to pay $154.

Are there nonstop flights from Chicago to Kentucky for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Kentucky under $200. A good price for a nonstop flight from Chicago to Kentucky is less than $215.

Are there last-minute flights available from Chicago to Kentucky for under $300?

There are currently 20+ open flights from Chicago to Kentucky within the next 7 days for less than $300.

What days are nonstop flights available from Chicago to Kentucky?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Chicago to Kentucky on average per day?

On average, you can expect to see 59 flights from Chicago to Kentucky a day.
Morning (6am - Noon) - 27% of flight departures
Afternoon (Noon - 6pm) - 22% of flight departures
Evening (6pm - Midnight) - 51% of flight departures

How long is the flight from Chicago to Kentucky?

Departing from Chicago to Kentucky will take you 1h 27m. The distance from Chicago to Kentucky is about 288 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $56. However, be on the lookout for offers from United Airlines and Contour, 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?

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: ANA (87%), Envoy Air (87%), GoJet (85%).

What are the cheapest flights from Chicago to Kentucky?

Looking at all options, your cheapest flight can be booked for $69. While the most popular route (Chicago O'Hare Intl - Lexington Blue Grass) can be booked for $177 on average our data indicates $208 when flying from Chicago to Kentucky.

What does ORD to SDF mean?

Great question - ORD to SDF just means Chicago O'Hare Intl Airport to Louisville Intl Airport. Now you’ll know what these unique codes when you look for flights! Lexington Blue Grass Airport (LEX), Paducah Barkley Regional Airport (PAH), Owensboro Daviess County Airport (OWB) are some additional IATA codes for airports related to your trip.

Destination points for flights from Chicago to Kentucky

Select to see more specific information for flights from Chicago to all places in Kentucky

Top 3 airlines flying from Chicago to Kentucky

The chart below displays the airlines Cheapflights users traveling from Chicago to Kentucky choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$130Average$264FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$134Average$237FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$166Average$226FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Hourly flight availability from Chicago to Kentucky

See what time of day planes typically take off from Chicago to Kentucky
1%of flight departuresEarly morningMidnight to 6 am
22%of flight departuresMorning6 am to noon
45%of flight departuresAfternoonNoon to 6 pm
32%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Fly with Cheapflights

What makes Cheapflights the go-to destination for all your flight needs

How does Cheapflights help users find flights from Chicago to Kentucky?

Cheapflights helps you search for flights from Chicago to Kentucky via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Kentucky?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Kentucky from Chicago.

Can Cheapflights find flights from Chicago to Kentucky with no change fees?

Yes! Cheapflights helps users easily find flights from Chicago to Kentucky with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Kentucky become cheaper?

Yes, Cheapflights has a feature called Price Alert, which essentially offers users the ability to be notified when flight prices change. Track prices for your flight to Kentucky from Chicago today and book when you’re ready!

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