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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 48% 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 $213, or $293 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, August can be a great choice for travel to Chicago. Flights to Chicago from Kentucky in August are about $182 on average during August, but can be found for as low as $64.

Cheap flights from Kentucky to Chicago in November, December 2020

The best prices found for Kentucky to CHI flights for November, December
14 Dec - 15 Dec
$126pp
SDF
Louisville Standiford Field
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SDF
Louisville Standiford Field
10 Dec - 16 Dec
$137pp
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
10 Dec - 17 Dec
$140pp
SDF
Louisville Standiford Field
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SDF
Louisville Standiford Field

Kentucky to Chicago 2021 flight deals

Cheap flights to Chicago from Kentucky found for next year
14 Dec - 15 Dec
$126pp
SDF
Louisville Standiford Field
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SDF
Louisville Standiford Field
10 Dec - 16 Dec
$137pp
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
10 Dec - 17 Dec
$140pp
SDF
Louisville Standiford Field
American Airlines
Non-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

Save time with Kentucky to Chicago direct flight deals
13 Feb - 27 Feb
$117pp
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
10 Dec - 16 Dec
$137pp
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
10 Mar - 26 Mar
$142pp
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

Last minute flights from Kentucky to Chicago

Late deals on round-trip flights to Chicago from Kentucky, departing today and this week
4 Dec - 11 Dec
$157pp
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
4 Dec - 11 Dec
$166pp
SDF
Louisville Standiford Field
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
SDF
Louisville Standiford Field
4 Dec - 11 Dec
$166pp
SDF
Louisville Standiford Field
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SDF
Louisville Standiford Field

One-way flights to Chicago from Kentucky

The cheapest one-way flights from Kentucky to Chicago
4:25 pm - 3:30 pm
Frontier
1 Stop
24h 05m
SDF - ORD
Frontier
$81
Kiwi.com
6:56 am - 4:43 am
Allegiant Air
1 Stop
22h 47m
SDF - MDW
Allegiant Air
$102
Kiwi.com
12:22 pm - 4:41 pm
American Airlines
1 Stop
5h 19m
SDF - ORD
American Airlines

Related info for your journey

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

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 $200 on Cheapflights?

Yes, there are multiple flights from Kentucky to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $117, but on average you can expect to pay $139.

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 $620.

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, Thursday, 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 Louisville Standiford Field - Chicago O'Hare Intl. You may also consider Lexington Blue Grass - Chicago O'Hare Intl or Lexington Blue Grass - Chicago Midway.

What are the cheapest Flights from Kentucky to Chicago?

On average you can expect to pay $205 for a flight from Kentucky to Chicago. The cheapest flight overall is $92 while the most popular route, (Louisville Standiford Field - Chicago O'Hare Intl) is currently priced at $126.

What are the most reliable airlines from Kentucky to Chicago?

The top 3 most reliable airlines when flying from Kentucky to Chicago are Qatar Airways (100%), Japan Airlines (100%) and Aer Lingus (100%).

How long is the flight from Kentucky to Chicago?

American Airlines, United Airlines, and Delta can get you from Kentucky to Chicago in just under 1h 26m. Your travel time can differ by up to 2h 29m. 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 $117. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $126 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 $59. Delta flights start at $63 while deals on Frontier start at $64 one-way.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Kentucky to Chicago
Flight duration
1h 27m
Average temperature for November in Chicago
51.8 °F
Avg rainfall for November in Chicago
2.4 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines 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.

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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