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Cheap flights from Kentucky to Illinois from $45

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 Illinois departing on 11/13. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Kentucky to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:10 pm - 7:35 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 25m2 stops Baltimore/Washington Greater Rochester Intl
Southwest Logo
8:05 am - 10:25 amMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
1h 20mnonstop
$172Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
7:15 pm - 7:25 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
2:00 pm - 8:55 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
5h 55m2 stops Lambert-St Louis Nashville Intl
$172Southwest
Wed, Sep 16 - Wed, Sep 23
Delta Logo
6:10 am - 9:17 amCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 1:28 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
2h 59m1 stop Detroit Metropolitan Wayne County
$177Delta
Mon, Sep 7 - Thu, Sep 10
Delta Logo
6:04 am - 9:17 amCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
4h 13m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 3:14 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
4h 45m1 stop Detroit Metropolitan Wayne County
$177Delta
Wed, Oct 14 - Sat, Oct 17
United Airlines Logo
9:00 am - 9:35 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 35mnonstop
United Airlines Logo
9:00 am - 11:26 amORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 26mnonstop
$181United Airlines
Thu, Sep 3 - Mon, Sep 7
United Airlines Logo
5:25 am - 5:55 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 30mnonstop
United Airlines Logo
6:59 am - 9:25 amORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 26mnonstop
$181United Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
8:52 am - 9:32 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 40mnonstop
American Airlines Logo
10:15 am - 12:39 pmORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 24mnonstop
$181American Airlines
Mon, Oct 5 - Wed, Oct 7
American Airlines Logo
8:48 am - 9:32 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 44mnonstop
American Airlines Logo
10:15 pm - 12:52 amORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 37mnonstop
$181American Airlines
Mon, Nov 16 - Thu, Nov 19
Contour Logo
8:00 am - 11:40 amBNA  Nashville Intl-ORD Chicago O'Hare Intl
3h 40m1 stop Quincy Regional
Contour Logo
12:30 pm - 4:10 pmORD  Chicago O'Hare Intl-BNA Nashville Intl
3h 40m1 stop Quincy Regional
$213Contour
Fri, Sep 18 - Sun, Sep 20
Contour Logo
8:00 am - 11:40 amBNA  Nashville Intl-ORD Chicago O'Hare Intl
3h 40m1 stop Quincy Regional
Contour Logo
12:30 pm - 4:10 pmORD  Chicago O'Hare Intl-BNA Nashville Intl
3h 40m1 stop Quincy Regional
$213Contour
Fri, Sep 4 - Mon, Sep 7

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Frontier flights from Kentucky to Illinois

Our best Frontier deals on Kentucky to Illinois flight tickets
Frontier
Sep 5
CVG8:30 pmCincinnati Cinci./N. Kentucky
18h 06m
1 stop
ORD1:36 pmChicago O'Hare Intl
Sep 12
ORD6:30 amChicago O'Hare Intl
8h 41m
1 stop
CVG4:11 pmCincinnati Cinci./N. Kentucky
$172
Frontier
Sep 25
CVG5:16 pmCincinnati Cinci./N. Kentucky
8h 07m
1 stop
ORD12:23 amChicago O'Hare Intl
Oct 8
ORD4:49 pmChicago O'Hare Intl
6h 14m
1 stop
CVG12:03 amCincinnati Cinci./N. Kentucky
$178
Frontier
Sep 5
CVG12:26 pmCincinnati Cinci./N. Kentucky
8h 42m
1 stop
ORD8:08 pmChicago O'Hare Intl
Sep 8
ORD5:29 pmChicago O'Hare Intl
25h 07m
1 stop
CVG7:36 pmCincinnati Cinci./N. Kentucky
$179

United Airlines flights from Kentucky to Illinois

Our best United Airlines deals on Kentucky to Illinois flight tickets
United Airlines
Sep 25
CVG5:30 amCincinnati Cinci./N. Kentucky
1h 29m
ORD5:59 amChicago O'Hare Intl
Sep 26
ORD12:53 pmChicago O'Hare Intl
1h 33m
CVG3:26 pmCincinnati Cinci./N. Kentucky
$181
United Airlines
Sep 12
SDF6:15 pmLouisville Intl
1h 49m
ORD7:04 pmChicago O'Hare Intl
Sep 14
ORD7:15 amChicago O'Hare Intl
1h 39m
SDF9:54 amLouisville Intl
$183
United Airlines
Sep 10
SDF11:00 amLouisville Intl
1h 42m
ORD11:42 amChicago O'Hare Intl
Sep 14
ORD9:20 pmChicago O'Hare Intl
1h 36m
SDF11:56 pmLouisville Intl
$195

momondo Fare Finder

 
Customize your flight search to find flights from Kentucky to Illinois 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 August 17, 2026.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 9/10

2:10 pm-7:35 pm

2 stops6h 25m

Chicago Midway

Mon 9/14

8:05 am-10:25 am

Nonstop1h 20m

$172

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 9/16

7:15 pm-7:25 pm

Nonstop1h 10m

Chicago Midway

Wed 9/23

2:00 pm-8:55 pm

2 stops5h 55m

$172

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 9/7

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Thu 9/10

9:29 am-1:28 pm

1 stop2h 59m

$177

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 10/14

6:04 am-9:17 am

1 stop4h 13m

Chicago Midway

Sat 10/17

9:29 am-3:14 pm

1 stop4h 45m

$177

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 9/3

9:00 am-9:35 am

Nonstop1h 35m

Chicago O'Hare Intl

Mon 9/7

9:00 am-11:26 am

Nonstop1h 26m

$181
Quickest round-trip

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 9/10

5:25 am-5:55 am

Nonstop1h 30m

Chicago O'Hare Intl

Thu 9/17

6:59 am-9:25 am

Nonstop1h 26m

$181

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 10/5

8:52 am-9:32 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 10/7

10:15 am-12:39 pm

Nonstop1h 24m

$181

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 11/16

8:48 am-9:32 am

Nonstop1h 44m

Chicago O'Hare Intl

Thu 11/19

10:15 pm-12:52 am

Nonstop1h 37m

$181

NashvilleChicago

BNA Nashville Intl - ORD Chicago O'Hare Intl

BNAORD

Nashville Intl

Fri 9/18

8:00 am-11:40 am

1 stop3h 40m

Chicago O'Hare Intl

Sun 9/20

12:30 pm-4:10 pm

1 stop3h 40m

$213

NashvilleChicago

BNA Nashville Intl - ORD Chicago O'Hare Intl

BNAORD

Nashville Intl

Fri 9/4

8:00 am-11:40 am

1 stop3h 40m

Chicago O'Hare Intl

Mon 9/7

12:30 pm-4:10 pm

1 stop3h 40m

$213

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Kentucky to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Kentucky is in October. Flight prices, which tend to average around $236, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $252.

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

The cheapest day to depart from Kentucky to Illinois is on a Friday when prices can be found for as low as $488. Flights from Kentucky to Illinois on a Sunday will generally be more expensive and average around $645. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Kentucky to Illinois during this time can be as low as $508. Flights at noon are often more expensive with an average ticket price of $921.

What is the cheapest Kentucky to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $328 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Kentucky for as low as $114 on momondo.

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

There are 4 cabin classes available to choose from on Kentucky to Illinois 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 Illinois flights?

You could potentially save up to 39% on your flight if you consider stops on a Kentucky to Illinois flight.

Cheap Kentucky to Illinois flight deals and tips

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

Best Price Found

$45

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Kentucky in the past 72 hours is $45. The best round-trip flight deal from Kentucky to Illinois found on momondo in the last 72 hours is $172.
The fastest flight from Kentucky to Illinois takes 1h 05m
Direct flights go from Kentucky to Illinois every day.
There are 98 airports in Illinois. From Kentucky there are direct flights to Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Kentucky to Illinois

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kentucky to Illinois.

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

    The required travel and health documents for your Illinois 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 Illinois. 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 Illinois?

Best airlines flying from Kentucky to Illinois

Compare and see reviews for airlines that fly from Kentucky to Illinois with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $77Free CancellationRating
8.0
4,218 reviews
Search Southwest flights
ContourPriceFrom $104Free CancellationRating
7.5
43 reviews
Search Contour flights
American AirlinesPriceFrom $152Free CancellationRating
7.1
11,948 reviews
Search American Airlines flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
10,106 reviews
Search United Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Kentucky to Illinois for you.

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

Flights from Kentucky to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Kentucky to Illinois.

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

Yes. momondo can track prices for Kentucky to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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