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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 12/25. 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
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Find the cheapest flights from Chicago Midway Airport to Kentucky

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:05 am - 12:30 pmMDW-SDF
1h 25mnonstop
Southwest Logo
3:20 pm - 9:05 pmSDF-MDW
6h 45m1 stop
$111Southwest
Find Deal
qua, dez 3 - qua, dez 3
Southwest Logo
6:40 am - 1:15 pmMDW-SDF
5h 35m1 stop
Southwest Logo
3:20 pm - 9:05 pmSDF-MDW
6h 45m1 stop
$121Southwest
Find Deal
qua, dez 3 - qua, dez 3
Multiple Airlines Logo
9:07 pm - 6:17 pmMDW-BNA
21h 10m1 stop
Multiple Airlines Logo
9:47 pm - 9:13 amBNA-MDW
11h 26m1 stop
$144Multiple Airlines
Find Deal
qui, jan 8 - dom, jan 11
Delta Logo
5:29 pm - 11:59 pmMDW-SDF
5h 30m1 stop
Delta Logo
6:00 am - 11:55 amSDF-MDW
6h 55m1 stop
$157Delta
Find Deal
ter, dez 9 - qua, dez 10
Frontier Logo
9:07 pm - 6:17 pmMDW-BNA
21h 10m1 stop
Frontier Logo
7:12 pm - 9:13 amBNA-MDW
14h 01m2 stops
$162Frontier
Find Deal
qui, jan 8 - dom, jan 11
Delta Logo
9:29 am - 1:28 pmMDW-BNA
3h 59m1 stop
Delta Logo
6:25 am - 11:55 amBNA-MDW
5h 30m1 stop
$168Delta
Find Deal
sáb, dez 13 - seg, dez 15
Multiple Airlines Logo
6:00 am - 6:17 pmMDW-BNA
12h 17m2 stops
Multiple Airlines Logo
9:47 pm - 9:13 amBNA-MDW
11h 26m1 stop
$173Multiple Airlines
Find Deal
qui, jan 8 - dom, jan 11
Frontier Logo
10:12 am - 12:19 pmMDW-BNA
26h 07m1 stop
Frontier Logo
3:42 pm - 11:30 amBNA-MDW
19h 48m1 stop
$190Frontier
Find Deal
qui, nov 13 - sáb, nov 15
Allegiant Air Logo
4:12 pm - 6:37 pmMDW-TYS
1h 25mnonstop
Allegiant Air Logo
5:49 pm - 6:46 pmTYS-MDW
25h 57m2 stops
$211Allegiant Air
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seg, nov 17 - qui, nov 20
Allegiant Air Logo
12:52 pm - 11:14 pmMDW-TYS
9h 22m2 stops
Allegiant Air Logo
12:45 pm - 1:21 pmTYS-MDW
1h 36mnonstop
$227Allegiant Air
Find Deal
seg, nov 17 - sex, nov 21

Frontier flights from Chicago Midway Airport to Kentucky

Our best Frontier deals on Chicago Midway Airport to Kentucky flight tickets
Frontier
Jan 8
MDW9:07 pmChicago Midway
21h 10m
1 stop
BNA6:17 pmNashville Intl
Jan 11
BNA7:12 pmNashville Intl
14h 01m
2 stops
MDW9:13 amChicago Midway
$162
Find similar
Frontier
Nov 13
MDW10:12 amChicago Midway
26h 07m
1 stop
BNA12:19 pmNashville Intl
Nov 15
BNA3:42 pmNashville Intl
19h 48m
1 stop
MDW11:30 amChicago Midway
$190
Find similar
Frontier
Dec 4
MDW6:15 amChicago Midway
31h 46m
2 stops
BNA2:01 pmNashville Intl
Dec 7
BNA6:45 pmNashville Intl
16h 23m
1 stop
MDW11:08 amChicago Midway
$199
Find similar

Delta flights from Chicago Midway Airport to Kentucky

Our best Delta deals on Chicago Midway Airport to Kentucky flight tickets
Delta
Dec 9
MDW5:29 pmChicago Midway
5h 30m
1 stop
SDF11:59 pmLouisville Intl
Dec 10
SDF6:00 amLouisville Intl
6h 55m
1 stop
MDW11:55 amChicago Midway
$157
Find similar
Delta
Dec 13
MDW9:29 amChicago Midway
3h 59m
1 stop
BNA1:28 pmNashville Intl
Dec 15
BNA6:25 amNashville Intl
5h 30m
1 stop
MDW11:55 amChicago Midway
$168
Find similar
Delta
Dec 4
MDW5:13 pmChicago Midway
4h 31m
1 stop
BNA9:44 pmNashville Intl
Dec 7
BNA7:33 amNashville Intl
4h 22m
1 stop
MDW11:55 amChicago Midway
$177
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Kentucky 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 novembro 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

qua 12/3

10:05 am-12:30 pm

Nonstop1h 25m

Louisville Intl

qua 12/3

3:20 pm-9:05 pm

1 stop6h 45m

$111

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

qua 12/3

6:40 am-1:15 pm

1 stop5h 35m

Louisville Intl

qua 12/3

3:20 pm-9:05 pm

1 stop6h 45m

$121

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

qui 1/8

9:07 pm-6:17 pm

1 stop21h 10m

Nashville Intl

dom 1/11

9:47 pm-9:13 am

1 stop11h 26m

$144

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

ter 12/9

5:29 pm-11:59 pm

1 stop5h 30m

Louisville Intl

qua 12/10

6:00 am-11:55 am

1 stop6h 55m

$157

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

qui 1/8

9:07 pm-6:17 pm

1 stop21h 10m

Nashville Intl

dom 1/11

7:12 pm-9:13 am

2 stops14h 01m

$162

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

sáb 12/13

9:29 am-1:28 pm

1 stop3h 59m

Nashville Intl

seg 12/15

6:25 am-11:55 am

1 stop5h 30m

$168

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

qui 1/8

6:00 am-6:17 pm

2 stops12h 17m

Nashville Intl

dom 1/11

9:47 pm-9:13 am

1 stop11h 26m

$173

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

qui 11/13

10:12 am-12:19 pm

1 stop26h 07m

Nashville Intl

sáb 11/15

3:42 pm-11:30 am

1 stop19h 48m

$190

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

seg 11/17

4:12 pm-6:37 pm

Nonstop1h 25m

Knoxville McGhee Tyson

qui 11/20

5:49 pm-6:46 pm

2 stops25h 57m

$211

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

seg 11/17

12:52 pm-11:14 pm

2 stops9h 22m

Knoxville McGhee Tyson

sex 11/21

12:45 pm-1:21 pm

Nonstop1h 36m

$227

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 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 month to fly to Kentucky?

If you’re not able to fly to Kentucky in September, then August is your next best option. Flight prices from Chicago Midway Airport to Kentucky during August average around $213.

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

Our data shows that Thursday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $241. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $582. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.

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

According to our data, the cheapest time of day to fly to Kentucky is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Kentucky in the afternoon for as low as $276. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Kentucky is in the morning when prices are around $350.

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 is only 1 cabin class 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Kentucky.

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

$147

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Kentucky

2 airports
The best one-way flight to Kentucky from Chicago Midway Airport in the past 72 hours is $147. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $263.
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 2 airports near Kentucky: Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG)
Search flight deals

  • 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 $129Free CancellationRating
8.0
4,239 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.

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qui 12/4
qui 12/11
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