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Cheap flights from Chicago Midway Airport to Kentucky from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Kentucky departing on 12/11. 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 Chicago Midway Airport to Kentucky

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Kentucky 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 Chicago Midway Airport to Kentucky.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Kentucky? 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 Kentucky, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Kentucky

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

All round-trip flight deals to Kentucky

The cheapest plane tickets to Kentucky found on KAYAK recently.
7:30 pm - 9:00 pmMDW-BNA
1h 30mnonstop
4:15 pm - 5:50 pmBNA-MDW
1h 35mnonstop
$98Southwest
Find Deal
Wed, Dec 11 - Sat, Dec 14
7:30 pm - 9:00 pmMDW-BNA
1h 30mnonstop
7:00 am - 11:45 amBNA-MDW
4h 45m1 stop
$107Southwest
Find Deal
Wed, Dec 11 - Sun, Dec 15
7:25 am - 8:30 pmMDW-CVG
12h 05m1 stop
8:00 am - 3:21 pmCVG-MDW
8h 21m1 stop
$118Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
7:15 am - 1:44 pmMDW-BNA
6h 29m1 stop
5:43 pm - 12:17 amBNA-MDW
6h 34m1 stop
$126Frontier
Find Deal
Fri, Jan 24 - Sun, Jan 26
6:00 am - 11:59 amMDW-CVG
4h 59m1 stop
6:30 am - 12:46 pmCVG-MDW
7h 16m1 stop
$176Delta
Find Deal
Wed, Jan 8 - Wed, Jan 15
9:34 am - 1:49 pmMDW-CVG
3h 15m1 stop
10:30 am - 5:47 pmCVG-MDW
8h 17m2 stops
$181Delta
Find Deal
Wed, Jan 8 - Wed, Jan 15
12:05 pm - 12:34 amMDW-BNA
12h 29m2 stops
4:14 pm - 5:51 pmBNA-MDW
25h 37m3 stops
Wed, Dec 18 - Wed, Dec 25
1:05 pm - 1:07 pmMDW-BNA
24h 02m3 stops
12:55 pm - 8:45 amBNA-MDW
19h 50m2 stops
Mon, Jan 13 - Mon, Jan 20
7:14 pm - 10:15 pmMDW-LEX
26h 01m3 stops
5:54 pm - 6:32 pmLEX-MDW
25h 38m3 stops
$1,067WestJet
Find Deal
Fri, Dec 6 - Tue, Dec 10
9:30 am - 11:42 amMDW-SDF
25h 12m3 stops
6:35 pm - 6:32 pmSDF-MDW
24h 57m3 stops
$1,130WestJet
Find Deal
Wed, Dec 4 - Thu, Dec 5
7:30 pm - 9:00 pmMDW-BNA
1h 30mnonstop
$49Southwest
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Wed, Dec 11
5:24 pm - 11:59 pmMDW-CVG
5h 35m1 stop
$54Frontier
Find Deal
Tue, Jan 7
6:40 am - 1:23 pmMDW-BNA
6h 43m1 stop
$54Frontier
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Mon, Feb 24
6:55 pm - 8:25 pmMDW-BNA
1h 30mnonstop
$59Southwest
Find Deal
Tue, Feb 18
5:51 pm - 10:54 pmMDW-CVG
4h 03m1 stop
$88Delta
Find Deal
Tue, Dec 24
12:44 pm - 6:14 pmMDW-BNA
5h 30m1 stop
$88Delta
Find Deal
Wed, Dec 11
6:16 pm - 8:43 pmMDW-TYS
1h 27mnonstop
$93Allegiant Air
Find Deal
Wed, Nov 27
2:22 pm - 11:00 pmMDW-CVG
7h 38m1 stop
$133Allegiant Air
Find Deal
Sun, Mar 9
10:19 am - 11:34 amMDW-SDF
24h 15m3 stops
$375WestJet
Find Deal
Fri, Jan 10
1:26 pm - 11:34 amMDW-SDF
21h 08m3 stops
$376WestJet
Find Deal
Mon, Jan 20
3:14 pm - 5:41 pmMDW-TYS
1h 27mnonstop
1:50 pm - 2:24 pmTYS-MDW
1h 34mnonstop
$160Allegiant Air
Find Deal
Fri, Nov 22 - Mon, Nov 25
3:14 pm - 5:41 pmMDW-TYS
1h 27mnonstop
11:12 am - 11:46 amTYS-MDW
1h 34mnonstop
$252Allegiant Air
Find Deal
Mon, Nov 25 - Sun, Dec 1
3:14 pm - 5:41 pmMDW-TYS
1h 27mnonstop
7:08 pm - 1:10 pmTYS-MDW
19h 02m1 stop
Fri, Nov 22 - Mon, Nov 25
7:00 am - 7:42 pmMDW-BNA
12h 42m1 stop
10:06 am - 4:27 pmBNA-MDW
6h 21m1 stop
$353Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
12:43 pm - 7:14 pmMDW-LEX
5h 31m1 stop
6:24 am - 8:50 amLEX-MDW
3h 26m1 stop
$361Delta
Find Deal
Tue, Nov 26 - Thu, Nov 28
4:20 pm - 1:50 amMDW-CVG
8h 30m1 stop
6:00 am - 11:10 amCVG-MDW
6h 10m1 stop
$378Frontier
Find Deal
Fri, Nov 22 - Mon, Nov 25
1:20 pm - 2:45 pmMDW-BNA
1h 25mnonstop
7:20 am - 1:00 pmBNA-MDW
5h 40m1 stop
$429Southwest
Find Deal
Tue, Nov 26 - Sat, Nov 30
1:20 pm - 6:00 pmMDW-BNA
4h 40m1 stop
7:45 am - 11:55 amBNA-MDW
4h 10m1 stop
$438Southwest
Find Deal
Tue, Nov 26 - Sat, Nov 30
10:41 am - 3:00 pmMDW-TYS
3h 19m1 stop
5:30 am - 9:32 amTYS-MDW
5h 02m1 stop
$443Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
12:39 pm - 1:27 pmMDW-TYS
23h 48m1 stop
7:26 pm - 1:10 pmTYS-MDW
18h 44m1 stop
Tue, Nov 26 - Wed, Nov 27
9:00 am - 10:30 amMDW-BNA
1h 30mnonstop
1:05 pm - 2:40 pmBNA-MDW
1h 35mnonstop
$98Southwest
Find Deal
Wed, Dec 18 - Sat, Jan 11
7:30 pm - 9:40 pmMDW-SDF
1h 10mnonstop
7:25 am - 7:45 amSDF-MDW
1h 20mnonstop
$143Southwest
Find Deal
Wed, Dec 11 - Thu, Dec 12
6:20 am - 7:55 amMDW-BNA
1h 35mnonstop
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
$148Southwest
Find Deal
Thu, Dec 12 - Sun, Dec 15
5:00 pm - 6:25 pmMDW-BNA
1h 25mnonstop
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
$154Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
6:25 am - 8:00 amMDW-BNA
1h 35mnonstop
9:25 pm - 10:55 pmBNA-MDW
1h 30mnonstop
$158Southwest
Find Deal
Thu, Jan 23 - Sun, Jan 26
1:30 pm - 2:55 pmMDW-BNA
1h 25mnonstop
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
$168Southwest
Find Deal
Mon, Dec 9 - Fri, Dec 13
10:00 am - 12:15 pmMDW-SDF
1h 15mnonstop
6:35 pm - 6:50 pmSDF-MDW
1h 15mnonstop
$173Southwest
Find Deal
Wed, Dec 11 - Wed, Dec 11
6:25 am - 8:00 amMDW-BNA
1h 35mnonstop
7:30 am - 9:05 amBNA-MDW
1h 35mnonstop
$198Southwest
Find Deal
Sun, Dec 29 - Wed, Jan 1
7:05 pm - 9:15 pmMDW-CVG
1h 10mnonstop
7:15 am - 7:20 amCVG-MDW
1h 05mnonstop
$208Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
4:50 pm - 7:00 pmMDW-SDF
1h 10mnonstop
7:05 am - 7:20 amSDF-MDW
1h 15mnonstop
$208Southwest
Find Deal
Fri, Jan 24 - Sun, Jan 26

Southwest flights from Chicago Midway Airport to Kentucky

Our best Southwest deals on Chicago Midway Airport to Kentucky flight tickets
Southwest
Dec 11
MDW7:30 pmChicago Midway
1h 30m
BNA9:00 pmNashville Intl
Dec 14
BNA4:15 pmNashville Intl
1h 35m
MDW5:50 pmChicago Midway
Southwest
Dec 11
MDW7:30 pmChicago Midway
1h 30m
BNA9:00 pmNashville Intl
Dec 15
BNA7:00 amNashville Intl
4h 45m
1 stop
MDW11:45 amChicago Midway
Southwest
Dec 18
MDW5:30 pmChicago Midway
1h 30m
BNA7:00 pmNashville Intl
Dec 25
BNA8:45 pmNashville Intl
1h 35m
MDW10:20 pmChicago Midway

Frontier flights from Chicago Midway Airport to Kentucky

Our best Frontier deals on Chicago Midway Airport to Kentucky flight tickets
Frontier
Jan 23
MDW7:25 amChicago Midway
12h 05m
1 stop
CVG8:30 pmCincinnati Cinci./N. Kentucky
Jan 26
CVG8:00 amCincinnati Cinci./N. Kentucky
8h 21m
1 stop
MDW3:21 pmChicago Midway
Frontier
Jan 24
MDW7:15 amChicago Midway
6h 29m
1 stop
BNA1:44 pmNashville Intl
Jan 26
BNA5:43 pmNashville Intl
6h 34m
1 stop
MDW12:17 amChicago Midway
Frontier
Feb 7
MDW5:30 amChicago Midway
8h 32m
1 stop
CVG3:02 pmCincinnati Cinci./N. Kentucky
Feb 9
CVG8:00 amCincinnati Cinci./N. Kentucky
8h 21m
1 stop
MDW3:21 pmChicago Midway

See travel insights to Kentucky from

How to get the cheapest flight ticket from Chicago Midway Airport to Kentucky

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 day to depart on your flight to Kentucky?

Our data shows that Tuesday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $0. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $696. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.

What is the cheapest Chicago Midway to Kentucky flight route?

Fly from Chicago Midway to Louisville Intl for the best Chicago Midway - Kentucky flight prices

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

There are 1 cabin classes available to choose from on Chicago Midway to Kentucky 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 Chicago Midway Airport to Kentucky flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago Midway Airport to Kentucky flight.

Cheap Chicago Midway Airport to Kentucky flight deals and tips

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

Best Price Found

$49

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Kentucky

3 airports
The best one-way flight to Kentucky from Chicago Midway Airport in the past 72 hours is $49. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $98.
The fastest flight from Chicago Midway Airport to Kentucky takes 1h 05m
Direct flights go from Chicago Midway Airport to Kentucky every day.
There are 3 airports near Kentucky: Nashville Intl (BNA), Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG)

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Kentucky.

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

    The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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


Best airlines flying from Chicago Midway Airport to Kentucky

Compare and see reviews for airlines that fly from Chicago Midway Airport to Kentucky with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $118Free CancellationRating
8.1
5,005 reviews
Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to Kentucky flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Kentucky that suits you.

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

Yes. momondo allows you to filter the results for Chicago to Kentucky flights to just show those with flexible booking policies.

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

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 Chicago to Kentucky.

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

Price alerts on flights to Kentucky from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Kentucky trip

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Popular cities in Kentucky

Popular flights according to clicks in the last 7 days on momondo