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Lexington

$214+ Cheap flights from Midway (MDW) to Lexington (LEX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LEX
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
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Cheap flight deals from Midway to Lexington

Cheapest flights from Midway to Lexington
Explore the most affordable flight options available from Midway to Lexington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.

This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Sun 7/197:35 am
LEX
-
MDW
1 stop6h 03m
Delta
Deal found 6/22$269
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Tue 7/285:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 6/23$284
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Sat 7/115:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 6/21$299
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2011:05 am
MDW
-
LEX
1 stop5h 05m
Delta
Mon 7/275:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 6/22$314
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:10 pm
MDW
-
LEX
1 stop5h 45m
Delta
Sun 8/25:56 pm
LEX
-
MDW
1 stop5h 20m
Delta
Deal found 6/21$354
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:05 am
MDW
-
LEX
1 stop5h 06m
Delta
Sun 7/56:00 am
LEX
-
MDW
1 stop5h 09m
Delta
Deal found 6/21$359
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:25 pm
MDW
-
LEX
1 stop6h 42m
Delta
Mon 7/65:56 pm
LEX
-
MDW
1 stop5h 21m
Delta
Deal found 6/22$379
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:05 am
MDW
-
LEX
1 stop7h 09m
Delta
Sun 7/197:35 am
LEX
-
MDW
1 stop6h 03m
Delta
Deal found 6/23$394
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:10 pm
MDW
-
LEX
1 stop5h 45m
Delta
Mon 7/275:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 6/21$404
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Sun 7/197:35 am
LEX
-
MDW
1 stop6h 03m
Delta
Deal found 6/23$409
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:11 pm
MDW
-
LEX
1 stop5h 56m
Delta
Mon 7/135:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 6/22$439
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
MDW
-
LEX
1 stop5h 19m
Delta
Sun 6/287:35 am
LEX
-
MDW
1 stop6h 11m
Delta
Deal found 6/20$449

Find flight deals from Midway to Lexington

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Lexington (LEX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(Delta)

One-way from

$214
(Kiwi.com)

Popular in

June

Cheapest in

July

Average price

$487
Provider with most accurate pricing for Chicago Midway-Lexington Blue Grass flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Lexington Blue Grass flights.
Search Deals
From Chicago Midway to Lexington Blue Grass
Search Deals
One-way flight from Chicago Midway to Lexington Blue Grass
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Lexington 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, Cheapflights users made 2,558,603 searches. Data last updated June 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Lexington that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 8/13

10:54 am-5:11 pm

1 stop5h 17m

Lexington Blue Grass

Sun 8/16

6:00 am-9:59 am

1 stop4h 59m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 7/15

6:00 am-12:17 pm

1 stop5h 17m

Lexington Blue Grass

Wed 7/22

5:56 pm-10:15 pm

1 stop5h 19m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/22

10:35 am-5:10 pm

1 stop5h 35m

Lexington Blue Grass

Sun 10/25

6:00 am-9:52 am

1 stop4h 52m

$269
Quickest round-trip

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 8/29

6:05 am-12:11 pm

1 stop5h 06m

Lexington Blue Grass

Sun 8/30

6:00 am-9:59 am

1 stop4h 59m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 7/21

6:00 am-12:17 pm

1 stop5h 17m

Lexington Blue Grass

Tue 7/28

5:56 pm-10:15 pm

1 stop5h 19m

$284

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 7/8

6:00 am-12:17 pm

1 stop5h 17m

Lexington Blue Grass

Sat 7/11

5:56 pm-10:15 pm

1 stop5h 19m

$299

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Mon 7/20

11:05 am-5:10 pm

1 stop5h 05m

Lexington Blue Grass

Mon 7/27

5:56 pm-10:15 pm

1 stop5h 19m

$314

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 7/31

5:10 pm-11:55 pm

1 stop5h 45m

Lexington Blue Grass

Sun 8/2

5:56 pm-10:16 pm

1 stop5h 20m

$354

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 7/14

11:05 am-7:14 pm

1 stop7h 09m

Lexington Blue Grass

Sun 7/19

7:35 am-12:38 pm

1 stop6h 03m

$394

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 7/24

5:10 pm-11:55 pm

1 stop5h 45m

Lexington Blue Grass

Mon 7/27

5:56 pm-10:15 pm

1 stop5h 19m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Midway to Lexington

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Lexington in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Lexington flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Lexington flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Lexington flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Lexington flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Lexington flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Lexington

Have a flexible travel schedule? Discover the best time to fly to Lexington from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Lexington. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Lexington from Chicago Midway?

    For a flight from Chicago Midway to Lexington, you will be flying into Blue Grass. Lexington Blue Grass (LEX) is just 5.6 mi from the center of the city. Blue Grass is the only Lexington airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Lexington Blue Grass from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Lexington?

    For as low as $269, Delta can have you in Lexington from Chicago Midway Airport in 5h 17m. Chicago Midway Airport and Lexington are separated by a distance of 308 mi.

  • Can I find deals for flights from Midway to Lexington that include hotel bookings?

    Yes. In addition to deals on Midway to Lexington flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Lexington?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Lexington.

  • Can I find deals for business class flights from Midway to Lexington?

    Yes. Cheapflights offers flight deals from Midway to Lexington by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Somerset
Richmond
Danville
Berea
Frankfort
Georgetown

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