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Cheap flights from Kentucky to Chicago from $41

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 2/21. 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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Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Kentucky to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Kentucky to Chicago.

Cheap last minute flights

Planning a quick getaway from Kentucky to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Kentucky to Chicago

Find recent round-trip train or bus tickets from Kentucky to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
2:23 pm - 4:21 pmBNA-ORD
1h 58mnonstop
3:50 pm - 5:29 pmORD-BNA
1h 39mnonstop
$63Frontier
Find Deal
Mon, Mar 3 - Wed, Mar 5
1:30 pm - 3:23 pmBNA-ORD
1h 53mnonstop
2:45 pm - 4:22 pmORD-BNA
1h 37mnonstop
$68Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
5:43 pm - 7:36 pmBNA-ORD
1h 53mnonstop
5:50 am - 11:47 amORD-BNA
5h 57m1 stop
Thu, Jan 9 - Sat, Jan 11
2:45 pm - 4:20 pmBNA-MDW
1h 35mnonstop
3:15 pm - 4:45 pmMDW-BNA
1h 30mnonstop
$129Southwest
Find Deal
Sat, Feb 8 - Tue, Feb 11
10:58 am - 12:47 pmBNA-ORD
1h 49mnonstop
8:20 pm - 10:08 pmORD-BNA
1h 48mnonstop
$137American Airlines
Find Deal
Thu, Jan 23 - Tue, Feb 4
6:00 am - 4:06 pmBNA-ORD
10h 06m1 stop
2:45 pm - 4:22 pmORD-BNA
1h 37mnonstop
Wed, Dec 18 - Wed, Dec 25
2:30 pm - 4:05 pmBNA-MDW
1h 35mnonstop
2:05 pm - 3:35 pmMDW-BNA
1h 30mnonstop
$149Southwest
Find Deal
Thu, Jan 9 - Sat, Jan 11
10:58 am - 12:47 pmBNA-ORD
1h 49mnonstop
2:12 pm - 3:48 pmORD-BNA
1h 36mnonstop
$158American Airlines
Find Deal
Wed, Jan 8 - Mon, Jan 13
7:00 am - 8:02 amTYS-ORD
2h 02mnonstop
2:10 pm - 4:59 pmORD-TYS
1h 49mnonstop
$169United Airlines
Find Deal
Thu, Jan 16 - Thu, Jan 23
9:35 am - 2:34 pmTYS-ORD
5h 59m1 stop
2:10 pm - 4:59 pmORD-TYS
1h 49mnonstop
$179United Airlines
Find Deal
Thu, Jan 16 - Thu, Jan 23
2:23 pm - 4:21 pmBNA-ORD
1h 58mnonstop
$41Frontier
Find Deal
Fri, Feb 21
2:54 pm - 4:47 pmBNA-ORD
1h 53mnonstop
$42Frontier
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Sun, Dec 15
12:00 pm - 1:35 pmBNA-MDW
1h 35mnonstop
$59Southwest
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Wed, Feb 19
12:40 pm - 2:35 pmBNA-ORD
1h 55mnonstop
$59United Airlines
Find Deal
Tue, Jan 7
2:40 pm - 4:15 pmBNA-MDW
1h 35mnonstop
$70Southwest
Find Deal
Sat, Jan 11
6:00 am - 8:05 amBNA-ORD
2h 05mnonstop
$70United Airlines
Find Deal
Sat, Jan 11
11:45 am - 10:59 pmBNA-ORD
11h 14m1 stop
$71Spirit Airlines
Find Deal
Tue, Dec 17
11:43 am - 12:37 pmTYS-ORD
1h 54mnonstop
$85American Airlines
Find Deal
Sat, Jan 25
9:14 pm - 7:19 pmBNA-ORD
22h 05m2 stops
$91Spirit Airlines
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Tue, Jan 7
6:25 am - 7:05 amLEX-ORD
1h 40mnonstop
$95American Airlines
Find Deal
Wed, Dec 18
3:46 pm - 5:37 pmBNA-ORD
1h 51mnonstop
1:20 pm - 2:56 pmORD-BNA
1h 36mnonstop
$244Frontier
Find Deal
Tue, Nov 26 - Fri, Nov 29
3:46 pm - 5:37 pmBNA-ORD
1h 51mnonstop
1:20 pm - 2:56 pmORD-BNA
1h 36mnonstop
$248Frontier
Find Deal
Thu, Nov 28 - Fri, Nov 29
8:05 pm - 8:21 amBNA-ORD
12h 16m1 stop
1:20 pm - 2:56 pmORD-BNA
1h 36mnonstop
Wed, Nov 27 - Fri, Nov 29
6:48 pm - 7:50 pmTYS-ORD
2h 02mnonstop
6:35 pm - 9:27 pmORD-TYS
1h 52mnonstop
$294American Airlines
Find Deal
Wed, Nov 27 - Mon, Dec 2
11:26 am - 4:02 pmTYS-ORD
5h 36m1 stop
6:35 pm - 9:27 pmORD-TYS
1h 52mnonstop
$304American Airlines
Find Deal
Wed, Nov 27 - Mon, Dec 2
5:30 am - 8:15 amTYS-ORD
3h 45m1 stop
5:45 pm - 11:50 pmORD-TYS
5h 05m1 stop
$313Delta
Find Deal
Wed, Nov 27 - Mon, Dec 2
6:00 am - 7:53 amBNA-ORD
1h 53mnonstop
10:35 am - 6:15 pmORD-BNA
7h 40m2 stops
$313United Airlines
Find Deal
Thu, Nov 28 - Thu, Nov 28
4:52 pm - 5:26 pmTYS-MDW
1h 34mnonstop
7:00 am - 6:15 pmMDW-TYS
10h 15m1 stop
Wed, Nov 27 - Fri, Nov 29
2:35 pm - 7:43 amSDF-ORD
18h 08m2 stops
10:35 am - 1:08 pmORD-SDF
1h 33mnonstop
$348United Airlines
Find Deal
Wed, Nov 27 - Thu, Nov 28
12:23 pm - 5:02 pmTYS-MDW
5h 39m1 stop
12:43 pm - 6:54 pmMDW-TYS
5h 11m1 stop
$353Delta
Find Deal
Wed, Nov 27 - Mon, Dec 2
1:30 pm - 3:23 pmBNA-ORD
1h 53mnonstop
2:45 pm - 4:22 pmORD-BNA
1h 37mnonstop
$53Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
1:30 pm - 3:23 pmBNA-ORD
1h 53mnonstop
2:45 pm - 4:22 pmORD-BNA
1h 37mnonstop
$55Frontier
Find Deal
Wed, Dec 18 - Wed, Dec 25
5:43 pm - 7:36 pmBNA-ORD
1h 53mnonstop
3:09 pm - 4:46 pmORD-BNA
1h 37mnonstop
$57Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
2:43 pm - 4:36 pmBNA-ORD
1h 53mnonstop
3:09 pm - 4:46 pmORD-BNA
1h 37mnonstop
$58Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
2:45 pm - 4:20 pmBNA-MDW
1h 35mnonstop
3:15 pm - 4:45 pmMDW-BNA
1h 30mnonstop
$129Southwest
Find Deal
Sat, Feb 8 - Tue, Feb 11
10:58 am - 12:47 pmBNA-ORD
1h 49mnonstop
8:20 pm - 10:08 pmORD-BNA
1h 48mnonstop
$137American Airlines
Find Deal
Thu, Jan 23 - Tue, Feb 4
7:13 am - 9:08 amBNA-ORD
1h 55mnonstop
8:20 pm - 10:08 pmORD-BNA
1h 48mnonstop
$148American Airlines
Find Deal
Thu, Jan 9 - Sat, Jan 11
2:30 pm - 4:05 pmBNA-MDW
1h 35mnonstop
2:05 pm - 3:35 pmMDW-BNA
1h 30mnonstop
$149Southwest
Find Deal
Thu, Jan 9 - Sat, Jan 11
7:00 am - 8:01 amTYS-ORD
2h 01mnonstop
10:35 am - 1:23 pmORD-TYS
1h 48mnonstop
$184United Airlines
Find Deal
Fri, Dec 13 - Mon, Dec 16
6:05 pm - 6:54 pmLEX-ORD
1h 49mnonstop
8:00 pm - 10:29 pmORD-LEX
1h 29mnonstop
$189United Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21

Delta flights from Kentucky to Chicago

Our best Delta deals on Kentucky to Chicago flight tickets
Delta
Jan 23
BNA6:15 amNashville Intl
6h 40m
1 stop
ORD12:55 pmChicago O'Hare Intl
Feb 4
ORD5:15 pmChicago O'Hare Intl
5h 27m
1 stop
BNA10:42 pmNashville Intl
Delta
Jan 9
TYS5:45 amKnoxville McGhee Tyson
5h 10m
1 stop
ORD9:55 amChicago O'Hare Intl
Jan 13
ORD12:35 pmChicago O'Hare Intl
6h 58m
1 stop
TYS8:33 pmKnoxville McGhee Tyson
Delta
Dec 10
BNA2:07 pmNashville Intl
6h 21m
1 stop
ORD8:28 pmChicago O'Hare Intl
Dec 17
ORD7:00 amChicago O'Hare Intl
4h 44m
1 stop
BNA11:44 amNashville Intl

United Airlines flights from Kentucky to Chicago

Our best United Airlines deals on Kentucky to Chicago flight tickets
United Airlines
Jan 16
TYS7:00 amKnoxville McGhee Tyson
2h 02m
ORD8:02 amChicago O'Hare Intl
Jan 23
ORD2:10 pmChicago O'Hare Intl
1h 49m
TYS4:59 pmKnoxville McGhee Tyson
United Airlines
Jan 16
TYS9:35 amKnoxville McGhee Tyson
5h 59m
1 stop
ORD2:34 pmChicago O'Hare Intl
Jan 23
ORD2:10 pmChicago O'Hare Intl
1h 49m
TYS4:59 pmKnoxville McGhee Tyson
United Airlines
Dec 13
TYS7:00 amKnoxville McGhee Tyson
2h 01m
ORD8:01 amChicago O'Hare Intl
Dec 16
ORD10:35 amChicago O'Hare Intl
1h 48m
TYS1:23 pmKnoxville McGhee Tyson

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 August is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $191. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Kentucky to Chicago during January average around $216.

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 Tuesday when prices can be found for as low as $177. 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 $295.

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 $244. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $281.

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?

The best time to book a flight to Chicago from Kentucky is 39 days out, which is when prices tend to be around $249. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $116.

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 208% 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

$41

Fastest flight time

1h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Kentucky in the past 72 hours is $41. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $63.
The fastest flight from Kentucky to Chicago takes 1h 00m
Direct flights go from Kentucky to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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
United AirlinesPriceFrom $110Free CancellationRating
7.4
9,156 reviews
Search United Airlines flights
American AirlinesPriceFrom $111Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
ContourPriceFrom $117Free CancellationRating
7.3
27 reviews
Search Contour flights
DeltaPriceFrom $135Free CancellationRating
8.0
8,734 reviews
Search Delta flights
SouthwestPriceFrom $156Free CancellationRating
8.1
4,984 reviews
Search Southwest flights

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