Cheap flights from Kentucky to Chicago (CHI)

SDF — CHI
Aug 13 — Aug 201

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

Users have found that booking a flight from Kentucky to Chicago at least 42 days early can save you up to 83% on average compared to booking a flight this week. If booking 42 days before your flight isn’t an option for you, users have found flights from Kentucky to Chicago for as little as $262 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $363 for flights departing within the next 3 days.

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

February is one of the best times of the year to fly to Chicago from Kentucky. Prices for February average $239 per person but you can even find prices for as low as $107. The most expensive prices can be found in the month of June. Opting for a February flight can save you 58% on your journey compared to booking in June

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

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

Cheap flights from Kentucky to Chicago in August, September 2022

The best prices found for Kentucky to CHI flights for August, September
Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 32m
$175

United Airlines

Pick Dates

Deal found 8/6/22

Sep 3 - Sep 10
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 34m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$180

United Airlines

Pick Dates

Deal found 8/7/22

Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

1 stop

3h 56m
$182

Multiple Airlines

Pick Dates

Deal found 8/6/22

Kentucky to Chicago 2022 flight deals

Cheap flights to Chicago from Kentucky found for this year
Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 32m
$175

United Airlines

Pick Dates

Deal found 8/6/22

Sep 3 - Sep 10
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 34m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$180

United Airlines

Pick Dates

Deal found 8/7/22

Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

1 stop

3h 56m
$182

Multiple Airlines

Pick Dates

Deal found 8/6/22

Cheap United Airlines flights from Kentucky to Chicago

Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 32m
$175

United Airlines

Pick Dates

Deal found 8/6/22

Sep 3 - Sep 10
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 34m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$180

United Airlines

Pick Dates

Deal found 8/7/22

Sep 2 - Sep 4
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 29m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 26m
$186

United Airlines

Pick Dates

Deal found 8/7/22

Cheap American Airlines flights from Kentucky to Chicago

Aug 26 - Aug 28
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 29m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$189

American Airlines

Pick Dates

Deal found 8/5/22

Aug 26 - Aug 28
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

1 stop

6h 52m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$195

American Airlines

Pick Dates

Deal found 8/6/22

Aug 26 - Aug 28
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

1 stop

4h 30m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$196

American Airlines

Pick Dates

Deal found 8/5/22

Non-stop flights to Chicago from Kentucky

Save time with Kentucky to Chicago direct flight deals
Sep 3 - Sep 20
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 39m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 32m
$175

United Airlines

Pick Dates

Deal found 8/6/22

Sep 3 - Sep 10
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 34m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 24m
$180

United Airlines

Pick Dates

Deal found 8/7/22

Sep 2 - Sep 4
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

Nonstop

1h 29m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

Nonstop

1h 26m
$186

United Airlines

Pick Dates

Deal found 8/7/22

Last minute flights from Kentucky to Chicago

Late deals on return flights to Chicago from Kentucky, departing today and this week
Aug 13 - Sep 5
LEX

Lexington Blue Grass

MDW

Chicago Midway

1 stop

3h 22m
MDW

Chicago Midway

LEX

Lexington Blue Grass

1 stop

2h 59m
$281

Delta

Pick Dates

Deal found 8/6/22

Aug 17 - Aug 19
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

1 stop

7h 27m
ORD

Chicago O'Hare Intl

SDF

Louisville Standiford Field

1 stop

22h 08m
$292

Spirit Airlines

Pick Dates

Deal found 8/5/22

Aug 13 - Sep 5
LEX

Lexington Blue Grass

ORD

Chicago O'Hare Intl

Nonstop

1h 43m
ORD

Chicago O'Hare Intl

LEX

Lexington Blue Grass

Nonstop

1h 25m
$293

United Airlines

Pick Dates

Deal found 8/6/22

One-way flights to Chicago from Kentucky

The cheapest one-way flights from Kentucky to Chicago
Aug 29
SDF

Louisville Standiford Field

MDW

Chicago Midway

1 stop

13h 04m
$78

Multiple Airlines

Pick Dates

Deal found 8/5/22

Sep 11
SDF

Louisville Standiford Field

MDW

Chicago Midway

1 stop

19h 48m
$84

Multiple Airlines

Pick Dates

Deal found 8/8/22

Sep 11
SDF

Louisville Standiford Field

ORD

Chicago O'Hare Intl

1 stop

29h 43m
$91

Multiple Airlines

Pick Dates

Deal found 8/5/22

Related info for your journey

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

Which airlines flying from Kentucky to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, American Airlines, and Delta flying from Kentucky to Chicago have implemented new flexible cancellation policies.

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

Yes, there are multiple flights from Kentucky to Chicago for under $200. The cheapest flight booked recently is on United Airlines for just $175, but on average you can expect to pay $196.

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

Cheapflights has at least 20 direct flights from Kentucky to Chicago under $200. A good price for a nonstop flight from Kentucky to Chicago is less than $223.

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

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

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

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $106. United Airlines flights start at $109 while deals on American Airlines start at $117 one-way.

What are the most popular routes from Kentucky to Chicago?

The most popular flight routes from Kentucky to Chicago are Lexington Blue Grass - Chicago O'Hare Intl, Louisville Standiford Field - Chicago O'Hare Intl and Louisville Standiford Field - Chicago Midway.

What are the most popular airlines that fly from Kentucky to Chicago?

Consider American Airlines, Juneyao Airlines or SilkAir when booking your flight. These represent the most popular airlines when flying from Kentucky to Chicago.

What are the most reliable airlines from Kentucky to Chicago?

Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Aer Lingus (100%), GoJet (100%), Lufthansa( 98%).

What are the cheapest flights from Kentucky to Chicago?

On average you can expect to pay $283 for a flight from Kentucky to Chicago. The cheapest flight overall is $109 while the most popular route, (Lexington Blue Grass - Chicago O'Hare Intl) is currently priced at $206.

Departure points for flights from Kentucky to Chicago

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

Top 4 airlines flying from Kentucky to Chicago

The chart below displays the airlines Cheapflights users traveling from Kentucky to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
United AirlinesCheapest$97Average$247FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$117Average$295FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$132Average$283FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
Linear Air TaxiCheapest$1,926Average$4,781FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Linear Air Taxi flights

Hourly flight availability from Kentucky to Chicago

See what time of day planes typically take off from Kentucky to Chicago
38%of flight departuresEarly morningMidnight to 6 am
24%of flight departuresMorning6 am to noon
37%of flight departuresAfternoonNoon to 6 pm
1%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM