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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 37 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 37 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 $177, or $177 for flights within the next 24 hours.

Cheap flights from Kentucky to Chicago in August, September 2020

The best prices found for Kentucky to CHI flights for August, September
15 Aug - 14 Sep
$96pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SDF
Louisville Standiford Field
1 Aug - 3 Aug
$97pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SDF
Louisville Standiford Field
1 Aug - 6 Aug
$100pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SDF
Louisville Standiford Field

Kentucky to Chicago 2020 flight deals

Cheap flights to Chicago from Kentucky found for this year
15 Aug - 14 Sep
$96pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SDF
Louisville Standiford Field
1 Aug - 4 Aug
$97pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SDF
Louisville Standiford Field
1 Aug - 6 Aug
$100pp
SDF
Louisville Standiford Field
Multiple 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
1 Aug - 4 Aug
$97pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SDF
Louisville Standiford Field
2 Aug - 5 Aug
$107pp
SDF
Louisville Standiford Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SDF
Louisville Standiford Field
2 Aug - 2 Aug
$117pp
SDF
Louisville Standiford Field
Multiple 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
29 Jul - 31 Jul
$119pp
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
29 Jul - 31 Jul
$120pp
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
25 Jul - 30 Jul
$122pp
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

One-way flights to Chicago from Kentucky

The cheapest one-way flights from Kentucky to Chicago
9:15 am - 12:40 pm
Delta
1 Stop
4h 25m
LEX - ORD
Delta
$318
Delta
3:30 am - 10:29 am
Multiple Airlines
3 Stops
31h 59m
LEX - ORD
Multiple Airlines
$591
Kiwi.com
11:27 am - 12:45 pm
Linear Air Taxi
Nonstop
2h 18m
LEX - ORD
Linear Air Taxi
$2547
KAYAK

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.

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 Multiple Airlines for just $96, but on average you can expect to pay $115.

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 $636.

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 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 $205 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 $106.

What are the most reliable airlines from Kentucky to Chicago?

The top 3 most reliable airlines when flying from Kentucky to Chicago are Air New Zealand (100%), GoJet (99%) and Aer Lingus (99%).

How long is the flight from Kentucky to Chicago?

Major Airline, Linear Air Taxi, and Delta can get you from Kentucky to Chicago in just under 1h 29m. Your travel time can differ by up to 1h 51m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What is the cheapest airline to fly from Kentucky to Chicago round-trip?

Flying on Delta is currently your cheapest option to Chicago, with prices starting at $112.

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

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $59. Delta is not the only option available. At the moment, Linear Air Taxi is another option, for $2083.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Kentucky to Chicago
Flight duration
1h 29m
Average temperature for August in Chicago
82.4 °F
Avg rainfall for August in Chicago
3.9 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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