Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Kentucky to Chicago from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kentucky to Chicago departing on 2/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:32 pm - 2:20 pm
SDF
-
ORD
1h 48mnonstop
American Airlines Logo
8:49 pm - 11:19 pm
ORD
-
SDF
1h 30mnonstop
$133American Airlines
Tue, Feb 3 - Tue, Feb 3
Multiple Airlines Logo
8:12 pm - 10:36 pm
BNA
-
ORD
26h 24m1 stop
Multiple Airlines Logo
5:32 pm - 8:29 pm
ORD
-
BNA
26h 57m1 stop
$138Multiple Airlines
Wed, Jan 21 - Wed, Jan 28
Multiple Airlines Logo
2:51 pm - 10:36 pm
BNA
-
ORD
7h 45m1 stop
Multiple Airlines Logo
3:00 pm - 7:25 am
ORD
-
BNA
16h 25m1 stop
$142Multiple Airlines
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
9:00 am - 4:40 pm
CVG
-
ORD
8h 40m1 stop
Frontier Logo
9:25 am - 10:20 pm
ORD
-
CVG
11h 55m1 stop
$145Frontier
Sat, Jan 24 - Sat, Jan 31
Frontier Logo
7:14 pm - 2:26 pm
CVG
-
MDW
20h 12m1 stop
Frontier Logo
9:22 pm - 9:25 pm
MDW
-
CVG
23h 03m1 stop
$152Frontier
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
2:05 pm - 2:48 pm
SDF
-
ORD
1h 43mnonstop
United Airlines Logo
7:52 pm - 10:30 pm
ORD
-
SDF
1h 38mnonstop
$152United Airlines
Sat, Jan 17 - Tue, Jan 20
Spirit Airlines Logo
8:12 pm - 11:22 am
BNA
-
ORD
15h 10m1 stop
Spirit Airlines Logo
7:20 am - 7:43 pm
ORD
-
BNA
12h 23m1 stop
$152Spirit Airlines
Fri, Jan 23 - Tue, Jan 27
Delta Logo
10:41 am - 1:13 pm
SDF
-
ORD
3h 32m1 stop
Delta Logo
5:59 pm - 11:50 pm
ORD
-
SDF
4h 51m1 stop
$157Delta
Tue, Feb 3 - Tue, Feb 3
Spirit Airlines Logo
8:40 am - 9:03 pm
BNA
-
ORD
12h 23m1 stop
Spirit Airlines Logo
7:20 am - 7:43 pm
ORD
-
BNA
12h 23m1 stop
$160Spirit Airlines
Sat, Jan 17 - Sat, Jan 24
United Airlines Logo
6:45 am - 7:47 am
TYS
-
ORD
2h 02mnonstop
United Airlines Logo
7:35 am - 10:19 am
ORD
-
TYS
1h 44mnonstop
$189United Airlines
Fri, Feb 13 - Sun, Feb 15

United Airlines flights from Kentucky to Chicago

Our best United Airlines deals on Kentucky to Chicago flight tickets
United Airlines
Jan 17
SDF2:05 pmLouisville Intl
1h 43m
ORD2:48 pmChicago O'Hare Intl
Jan 20
ORD7:52 pmChicago O'Hare Intl
1h 38m
SDF10:30 pmLouisville Intl
$152
Find similar
United Airlines
Feb 13
TYS6:45 amKnoxville McGhee Tyson
2h 02m
ORD7:47 amChicago O'Hare Intl
Feb 15
ORD7:35 amChicago O'Hare Intl
1h 44m
TYS10:19 amKnoxville McGhee Tyson
$189
Find similar
United Airlines
Jan 21
CVG7:00 amCincinnati Cinci./N. Kentucky
1h 33m
ORD7:33 amChicago O'Hare Intl
Jan 21
ORD2:20 pmChicago O'Hare Intl
1h 23m
CVG4:43 pmCincinnati Cinci./N. Kentucky
$193
Find similar

Spirit Airlines flights from Kentucky to Chicago

Our best Spirit Airlines deals on Kentucky to Chicago flight tickets
Spirit Airlines
Jan 23
BNA8:12 pmNashville Intl
15h 10m
1 stop
ORD11:22 amChicago O'Hare Intl
Jan 27
ORD7:20 amChicago O'Hare Intl
12h 23m
1 stop
BNA7:43 pmNashville Intl
$152
Find similar
Spirit Airlines
Jan 17
BNA8:40 amNashville Intl
12h 23m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jan 24
ORD7:20 amChicago O'Hare Intl
12h 23m
1 stop
BNA7:43 pmNashville Intl
$160
Find similar
Spirit Airlines
Jan 17
BNA8:40 amNashville Intl
12h 23m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jan 25
ORD8:43 pmChicago O'Hare Intl
10h 42m
1 stop
BNA7:25 amNashville Intl
$161
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 26, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 2/3

1:32 pm-2:20 pm

Nonstop1h 48m

Chicago O'Hare Intl

Tue 2/3

8:49 pm-11:19 pm

Nonstop1h 30m

$133

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 1/21

8:12 pm-10:36 pm

1 stop26h 24m

Chicago O'Hare Intl

Wed 1/28

5:32 pm-8:29 pm

1 stop26h 57m

$138

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 2/5

2:51 pm-10:36 pm

1 stop7h 45m

Chicago O'Hare Intl

Sun 2/8

3:00 pm-7:25 am

1 stop16h 25m

$142

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 1/24

9:00 am-4:40 pm

1 stop8h 40m

Chicago O'Hare Intl

Sat 1/31

9:25 am-10:20 pm

1 stop11h 55m

$145

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/19

7:14 pm-2:26 pm

1 stop20h 12m

Chicago Midway

Mon 2/23

9:22 pm-9:25 pm

1 stop23h 03m

$152

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 1/17

2:05 pm-2:48 pm

Nonstop1h 43m

Chicago O'Hare Intl

Tue 1/20

7:52 pm-10:30 pm

Nonstop1h 38m

$152

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 1/23

8:12 pm-11:22 am

1 stop15h 10m

Chicago O'Hare Intl

Tue 1/27

7:20 am-7:43 pm

1 stop12h 23m

$152

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 2/3

10:41 am-1:13 pm

1 stop3h 32m

Chicago O'Hare Intl

Tue 2/3

5:59 pm-11:50 pm

1 stop4h 51m

$157

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 1/17

8:40 am-9:03 pm

1 stop12h 23m

Chicago O'Hare Intl

Sat 1/24

7:20 am-7:43 pm

1 stop12h 23m

$160

KnoxvilleChicago

TYS - ORD

TYSORD

Knoxville McGhee Tyson

Fri 2/13

6:45 am-7:47 am

Nonstop2h 02m

Chicago O'Hare Intl

Sun 2/15

7:35 am-10:19 am

Nonstop1h 44m

$189

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Kentucky to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $196. If you’re not able to fly to Chicago in November, then April is your next best option. Flight prices from Kentucky to Chicago during April average around $207.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $496. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Kentucky to Chicago for around $713.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Kentucky to Chicago during this time can be as low as $508. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $871.

What is the cheapest Kentucky to Chicago flight route?

Fly from Owensboro Daviess County to Chicago O'Hare Intl for the best Kentucky - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $302 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Kentucky for as low as $182 on momondo.

What cabin class options are available on Kentucky to Chicago flights?

There are 4 cabin classes available to choose from on Kentucky to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Kentucky to Chicago flights?

No. A direct flight is the cheapest option for a flight between Kentucky to Chicago.

Cheap Kentucky to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kentucky to Chicago

Best Price Found

$44

Fastest flight time

1h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Kentucky in the past 72 hours is $44. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $100.
The fastest flight from Kentucky to Chicago takes 1h 10m
Direct flights go from Kentucky to Chicago every day.
There are 3 airports in Chicago. From Kentucky there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from Kentucky to Chicago?

    Prices for flights from Kentucky to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Kentucky to Chicago?

  • How old do you have to be to fly from Kentucky to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Kentucky to Chicago?

Best airlines flying from Kentucky to Chicago

Compare and see reviews for airlines that fly from Kentucky to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $97Free CancellationRating
7.2
11,064 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
ContourPriceFrom $109Free CancellationRating
7.6
43 reviews
Search Contour flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
9,115 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Kentucky to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Kentucky to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Kentucky to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Kentucky which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Kentucky to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kentucky.

I’m not ready to book a flight from Kentucky to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Kentucky to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 1/25
Sun 2/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport