Cheap flights from Kentucky (KY) to Chicago (CHI)

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How to find the cheapest flight from
Kentucky to Chicago (CHI)

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

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Kentucky to Chicago 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Kentucky in April are about $135 on average during April, but can be found for as low as $33.

Cheap flights from Kentucky to Chicago in February, March 2021

18 Mar - 1 Apr
$99pp
SDF
Louisville Standiford Field
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
18 Mar - 1 Apr
$107pp
SDF
Louisville Standiford Field
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
18 Mar - 21 Mar
$119pp
SDF
Louisville Standiford Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SDF
Louisville Standiford Field

Kentucky to Chicago 2021 flight deals

18 Mar - 1 Apr
$99pp
SDF
Louisville Standiford Field
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
18 Mar - 1 Apr
$107pp
SDF
Louisville Standiford Field
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
15 Apr - 19 Apr
$114pp
SDF
Louisville Standiford Field
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SDF
Louisville Standiford Field

Non-stop flights to Chicago from Kentucky

18 Mar - 1 Apr
$99pp
SDF
Louisville Standiford Field
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
18 Mar - 21 Mar
$119pp
SDF
Louisville Standiford Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SDF
Louisville Standiford Field
17 Mar - 24 Mar
$139pp
LEX
Lexington Blue Grass
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
LEX
Lexington Blue Grass

Last minute flights from Kentucky to Chicago

3 Mar - 9 Mar
$194pp
SDF
Louisville Standiford Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SDF
Louisville Standiford Field
3 Mar - 6 Mar
$198pp
SDF
Louisville Standiford Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SDF
Louisville Standiford Field
4 Mar - 7 Mar
$216pp
SDF
Louisville Standiford Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SDF
Louisville Standiford Field

One-way flights to Chicago from Kentucky

6:11 am - 4:40 am
Allegiant Air
1 Stop
23h 29m
LEX - MDW
Allegiant Air
$123
Kiwi.com
4:56 am - 9:09 am
Multiple Airlines
1 Stop
29h 13m
LEX - ORD
Multiple Airlines
$143
Kiwi.com
8:33 am - 12:55 pm
American Airlines
1 Stop
5h 22m
SDF - ORD
American Airlines

Related info for your journey

Flight FAQs

From Kentucky to Chicago

Are flight prices decreasing from Kentucky to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Kentucky and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Kentucky to Chicago to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Kentucky to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 American Airlines, United Airlines, and Delta flying from Kentucky to Chicago have implemented new flexible cancellation policies.

Can I find flights from Kentucky to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Kentucky to Chicago for under $100. The cheapest flight booked recently is on American Airlines for just $99, but on average you can expect to pay $135.

Are there nonstop flights from Kentucky to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Kentucky to Chicago under $100. A good price for a nonstop flight from Kentucky to Chicago is less than $306.

Are there last-minute flights available from Kentucky to Chicago for under $200?

There are currently 20+ open flights from Kentucky to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Kentucky to Chicago?

You can find nonstop flights on the following days: Sunday, Tuesday, Friday, Saturday.

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

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

What are the most popular routes from Kentucky to Chicago?

The most popular route from Kentucky to Chicago is Lexington Blue Grass - Chicago O'Hare Intl. You may also consider Louisville Standiford Field - Chicago O'Hare Intl or Louisville Standiford Field - Chicago Midway.

What are the cheapest Flights from Kentucky to Chicago?

On average you can expect to pay $200 for a flight from Kentucky to Chicago. The cheapest flight overall is $92 while the most popular route, (Lexington Blue Grass - Chicago O'Hare Intl) is currently priced at $157.

What are the most reliable airlines from Kentucky to Chicago?

The top 3 most reliable airlines when flying from Kentucky to Chicago are Aer Lingus (96%), ANA (83%) and Air Canada (82%).

How long is the flight from Kentucky to Chicago?

United Airlines, American Airlines, and Delta can get you from Kentucky to Chicago in just under 1h 26m. Your travel time can differ by up to 1h 56m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Kentucky to Chicago round-trip?

Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $99. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $119 and $137, respectively.

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

To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $50. Delta flights start at $73 while deals on United Airlines start at $115 one-way.

Destination information for Chicago

Flight duration
1h 26m
Average temperature for February in Chicago
39.2 °F
Avg rainfall for February in Chicago
1.0 ″

Airports servicing

Owensboro (OWB)
Paducah (PAH)
Standiford Field (SDF)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Kentucky to Chicago

Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
$99 $266 No cancel fee 71%
United Airlines
$94 $269 No cancel fee 69%
Delta
$66 $322 No cancel fee N/A
Linear Air Taxi
$1,926 $4,781 No cancel fee N/A

We couldn't confirm the COVID-19 safety measures taken by Linear Air Taxi. Please check directly on their website for additional information.

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