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Cheap flights from Kentucky to Chicago from $68

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 7/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 10:50 pm
CVG
-
ORD
17h 50m
1 stop
Frontier Logo
6:08 pm - 5:33 pm
ORD
-
CVG
22h 25m
1 stop
$174Frontier
Thu, Apr 9 - Wed, Apr 15
United Airlines Logo
10:10 am - 10:46 am
CVG
-
ORD
1h 36mnonstop
United Airlines Logo
6:05 pm - 8:29 pm
ORD
-
CVG
1h 24mnonstop
$175United Airlines
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
7:35 pm - 7:50 pm
CVG
-
MDW
1h 15mnonstop
Southwest Logo
6:10 pm - 8:20 pm
MDW
-
CVG
1h 10mnonstop
$176Southwest
Tue, Jun 2 - Wed, Jun 3
Multiple Airlines Logo
6:00 am - 10:50 pm
CVG
-
ORD
17h 50m
1 stop
Multiple Airlines Logo
12:45 pm - 3:52 pm
ORD
-
CVG
26h 07m
1 stop
$184Multiple Airlines
Thu, Apr 9 - Tue, Apr 14
Southwest Logo
7:35 pm - 7:50 pm
CVG
-
MDW
1h 15mnonstop
Southwest Logo
3:00 pm - 9:15 pm
MDW
-
CVG
5h 15m
1 stop
$185Southwest
Wed, Apr 22 - Wed, Apr 29
Multiple Airlines Logo
3:05 pm - 11:17 pm
CVG
-
ORD
9h 12m
1 stop
Multiple Airlines Logo
6:08 pm - 3:52 pm
ORD
-
CVG
20h 44m
2 stops
$189Multiple Airlines
Sat, Apr 11 - Tue, Apr 14
Allegiant Air Logo
2:22 pm - 9:17 am
BNA
-
RFD
18h 55m
1 stop
Allegiant Air Logo
9:19 am - 10:44 am
RFD
-
BNA
1h 25mnonstop
$194Allegiant Air
Fri, Jun 5 - Sun, Jun 7
Spirit Airlines Logo
3:27 pm - 12:24 am
BNA
-
ORD
8h 57m
1 stop
Spirit Airlines Logo
7:15 pm - 8:35 am
ORD
-
BNA
13h 20m
1 stop
$194Spirit Airlines
Fri, Apr 17 - Tue, Apr 28
Spirit Airlines Logo
3:27 pm - 12:24 am
BNA
-
ORD
8h 57m
1 stop
Spirit Airlines Logo
7:15 pm - 8:35 am
ORD
-
BNA
13h 20m
1 stop
$195Spirit Airlines
Tue, Apr 21 - Tue, Apr 28
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
Allegiant Air Logo
2:47 pm - 5:13 pm
MDW
-
TYS
1h 26mnonstop
$199Allegiant Air
Thu, May 21 - Sun, May 24

Spirit Airlines flights from Kentucky to Chicago

Our best Spirit Airlines deals on Kentucky to Chicago flight tickets
Spirit Airlines
Apr 17
BNA3:27 pmNashville Intl
8h 57m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 28
ORD7:15 pmChicago O'Hare Intl
13h 20m
1 stop
BNA8:35 amNashville Intl
$194
Spirit Airlines
Apr 21
BNA3:27 pmNashville Intl
8h 57m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 28
ORD7:15 pmChicago O'Hare Intl
13h 20m
1 stop
BNA8:35 amNashville Intl
$195
Spirit Airlines
Apr 7
BNA7:44 amNashville Intl
9h 31m
1 stop
ORD5:15 pmChicago O'Hare Intl
Apr 9
ORD9:06 amChicago O'Hare Intl
10h 40m
1 stop
BNA7:46 pmNashville Intl
$199

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets
Frontier
Apr 9
CVG6:00 amCincinnati Cinci./N. Kentucky
17h 50m
1 stop
ORD10:50 pmChicago O'Hare Intl
Apr 15
ORD6:08 pmChicago O'Hare Intl
22h 25m
1 stop
CVG5:33 pmCincinnati Cinci./N. Kentucky
$174
Frontier
May 1
CVG3:32 pmCincinnati Cinci./N. Kentucky
9h 22m
1 stop
ORD11:54 pmChicago O'Hare Intl
May 3
ORD5:50 amChicago O'Hare Intl
11h 26m
1 stop
CVG6:16 pmCincinnati Cinci./N. Kentucky
$180
Frontier
Apr 16
CVG8:38 pmCincinnati Cinci./N. Kentucky
10h 30m
1 stop
ORD6:08 amChicago O'Hare Intl
Apr 19
ORD5:59 amChicago O'Hare Intl
10h 49m
1 stop
CVG5:48 pmCincinnati Cinci./N. Kentucky
$181

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 March 26, 2026.
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

Cheapest round-trip

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 4/9

6:00 am-10:50 pm

1 stop17h 50m

Chicago O'Hare Intl

Wed 4/15

6:08 pm-5:33 pm

1 stop22h 25m

$174

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Wed 4/22

10:10 am-10:46 am

Nonstop1h 36m

Chicago O'Hare Intl

Wed 4/29

6:05 pm-8:29 pm

Nonstop1h 24m

$175
Quickest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 6/2

7:35 pm-7:50 pm

Nonstop1h 15m

Chicago Midway

Wed 6/3

6:10 pm-8:20 pm

Nonstop1h 10m

$176

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 4/9

6:00 am-10:50 pm

1 stop17h 50m

Chicago O'Hare Intl

Tue 4/14

12:45 pm-3:52 pm

1 stop26h 07m

$184

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 4/22

7:35 pm-7:50 pm

Nonstop1h 15m

Chicago Midway

Wed 4/29

3:00 pm-9:15 pm

1 stop5h 15m

$185

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 4/11

3:05 pm-11:17 pm

1 stop9h 12m

Chicago O'Hare Intl

Tue 4/14

6:08 pm-3:52 pm

2 stops20h 44m

$189

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Fri 6/5

2:22 pm-9:17 am

1 stop18h 55m

Chicago Greater Rockford

Sun 6/7

9:19 am-10:44 am

Nonstop1h 25m

$194

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 4/17

3:27 pm-12:24 am

1 stop8h 57m

Chicago O'Hare Intl

Tue 4/28

7:15 pm-8:35 am

1 stop13h 20m

$194

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 4/21

3:27 pm-12:24 am

1 stop8h 57m

Chicago O'Hare Intl

Tue 4/28

7:15 pm-8:35 am

1 stop13h 20m

$195

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Sun 5/24

2:47 pm-5:13 pm

Nonstop1h 26m

$199

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 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 October is your next best option. Flight prices from Kentucky to Chicago during October average around $225.

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 $501. 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 $656.

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 $490. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $887.

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 $276 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 $141 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?

You could potentially save up to 31% on your flight if you consider stops on a Kentucky to Chicago flight.

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

$175

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Kentucky in the past 72 hours is $175. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $104.
The fastest flight from Kentucky to Chicago takes 1h 05m
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), Chicago Greater Rockford (RFD).
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
7.1
11,502 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,331 reviews
Search Southwest flights
ContourPriceFrom $104Free CancellationRating
7.6
42 reviews
Search Contour flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
9,493 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
Saint Joseph
Benton Harbor
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.

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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