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Cheap flights from Kentucky to Chicago from $71

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 8/2. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
1:22 pm - 1:58 pm
TYS
-
MDW
1h 36mnonstop
Allegiant Air Logo
2:48 pm - 5:18 pm
MDW
-
TYS
1h 30mnonstop
$155Allegiant Air
Thu, Jul 9 - Thu, Jul 16
Allegiant Air Logo
1:22 pm - 1:58 pm
TYS
-
MDW
1h 36mnonstop
Allegiant Air Logo
2:48 pm - 5:18 pm
MDW
-
TYS
1h 30mnonstop
$159Allegiant Air
Thu, Jul 9 - Thu, Jul 16
Southwest Logo
6:10 pm - 11:20 pm
CVG
-
MDW
6h 10m
1 stop
Southwest Logo
5:30 pm - 11:10 pm
MDW
-
CVG
4h 40m
1 stop
$177Southwest
Sat, Jul 25 - Wed, Jul 29
American Airlines Logo
10:30 am - 11:10 am
CVG
-
ORD
1h 40mnonstop
American Airlines Logo
10:00 pm - 12:24 am
ORD
-
CVG
1h 24mnonstop
$177American Airlines
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
2:50 pm - 8:30 pm
CVG
-
MDW
6h 40m
1 stop
Southwest Logo
8:05 am - 10:25 am
MDW
-
CVG
1h 20mnonstop
$178Southwest
Sat, Aug 8 - Mon, Aug 10
Delta Logo
6:05 am - 9:18 am
CVG
-
MDW
4h 13m
1 stop
Delta Logo
1:28 pm - 7:14 pm
MDW
-
CVG
4h 46m
1 stop
$187Delta
Tue, Oct 20 - Thu, Oct 22
Delta Logo
3:30 pm - 8:30 pm
CVG
-
ORD
6h 00m
1 stop
Delta Logo
5:20 pm - 10:40 pm
ORD
-
CVG
4h 20m
1 stop
$187Delta
Sat, Aug 8 - Mon, Aug 10
Multiple Airlines Logo
7:30 am - 12:50 pm
CVG
-
ORD
30h 20m
1 stop
Multiple Airlines Logo
8:05 am - 9:38 pm
ORD
-
CVG
12h 33m
1 stop
$189Multiple Airlines
Mon, Aug 31 - Thu, Sep 3
Multiple Airlines Logo
8:30 am - 12:50 pm
CVG
-
ORD
29h 20m
1 stop
Multiple Airlines Logo
8:05 am - 9:32 pm
ORD
-
CVG
12h 27m
1 stop
$200Multiple Airlines
Mon, Aug 24 - Thu, Aug 27
American Airlines Logo
8:58 am - 9:35 am
CVG
-
ORD
1h 37mnonstop
American Airlines Logo
6:46 pm - 9:20 pm
ORD
-
CVG
1h 34mnonstop
$215American Airlines
Sat, Jul 25 - Mon, Jul 27

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Delta flights from Kentucky to Chicago

Our best Delta deals on Kentucky to Chicago flight tickets
Delta
Aug 26
CVG10:53 amCincinnati Cinci./N. Kentucky
3h 15m
1 stop
ORD1:08 pmChicago O'Hare Intl
Aug 29
ORD5:18 pmChicago O'Hare Intl
4h 22m
1 stop
CVG10:40 pmCincinnati Cinci./N. Kentucky
$177
Delta
Aug 8
CVG3:30 pmCincinnati Cinci./N. Kentucky
6h 00m
1 stop
ORD8:30 pmChicago O'Hare Intl
Aug 10
ORD5:20 pmChicago O'Hare Intl
4h 20m
1 stop
CVG10:40 pmCincinnati Cinci./N. Kentucky
$187
Delta
Aug 8
CVG3:30 pmCincinnati Cinci./N. Kentucky
6h 00m
1 stop
ORD8:30 pmChicago O'Hare Intl
Aug 10
ORD5:20 pmChicago O'Hare Intl
4h 20m
1 stop
CVG10:40 pmCincinnati Cinci./N. Kentucky
$196

United Airlines flights from Kentucky to Chicago

Our best United Airlines deals on Kentucky to Chicago flight tickets
United Airlines
Aug 20
CVG12:29 pmCincinnati Cinci./N. Kentucky
1h 34m
ORD1:03 pmChicago O'Hare Intl
Aug 24
ORD4:38 pmChicago O'Hare Intl
1h 34m
CVG7:12 pmCincinnati Cinci./N. Kentucky
$195
United Airlines
Aug 15
SDF9:00 amLouisville Intl
1h 41m
ORD9:41 amChicago O'Hare Intl
Aug 19
ORD6:56 amChicago O'Hare Intl
1h 42m
SDF9:38 amLouisville Intl
$223
United Airlines
Aug 8
SDF7:55 pmLouisville Intl
1h 45m
ORD8:40 pmChicago O'Hare Intl
Aug 10
ORD9:25 pmChicago O'Hare Intl
1h 34m
SDF11:59 pmLouisville Intl
$224

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 June 29, 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

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 7/9

1:22 pm-1:58 pm

Nonstop1h 36m

Chicago Midway

Thu 7/16

2:48 pm-5:18 pm

Nonstop1h 30m

$155

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 7/9

1:22 pm-1:58 pm

Nonstop1h 36m

Chicago Midway

Thu 7/16

2:48 pm-5:18 pm

Nonstop1h 30m

$159

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 7/25

6:10 pm-11:20 pm

1 stop6h 10m

Chicago Midway

Wed 7/29

5:30 pm-11:10 pm

1 stop4h 40m

$177
Quickest round-trip

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 10/1

10:30 am-11:10 am

Nonstop1h 40m

Chicago O'Hare Intl

Mon 10/5

10:00 pm-12:24 am

Nonstop1h 24m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 8/8

2:50 pm-8:30 pm

1 stop6h 40m

Chicago Midway

Mon 8/10

8:05 am-10:25 am

Nonstop1h 20m

$178

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 10/20

6:05 am-9:18 am

1 stop4h 13m

Chicago Midway

Thu 10/22

1:28 pm-7:14 pm

1 stop4h 46m

$187

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 8/8

3:30 pm-8:30 pm

1 stop6h 00m

Chicago O'Hare Intl

Mon 8/10

5:20 pm-10:40 pm

1 stop4h 20m

$187

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 8/31

7:30 am-12:50 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 9/3

8:05 am-9:38 pm

1 stop12h 33m

$189

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 8/24

8:30 am-12:50 pm

1 stop29h 20m

Chicago O'Hare Intl

Thu 8/27

8:05 am-9:32 pm

1 stop12h 27m

$200

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 7/25

8:58 am-9:35 am

Nonstop1h 37m

Chicago O'Hare Intl

Mon 7/27

6:46 pm-9:20 pm

Nonstop1h 34m

$215

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 April is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $58. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Kentucky to Chicago during January average around $67.

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 Friday 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 $650.

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 $503. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $906.

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 from Kentucky 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 $308 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 $114 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 60% 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

$160

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 $160. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $164.
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).
Search flight deals

Frequently asked questions about flying from Kentucky to Chicago

  • 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
11,770 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
7.9
4,246 reviews
Search Southwest flights
ContourPriceFrom $108Free CancellationRating
7.7
42 reviews
Search Contour flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,894 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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