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$105+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LEX
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$209
(Delta)

One-way from

$105
(Delta)

Popular in

February

Cheapest in

January

Average price

$250
From Chicago Midway to Lexington Blue Grass
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One-way flight from Chicago Midway to Lexington Blue Grass
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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 9/151:08 pmMDW - LEX
1 stop3h 00mDelta
Tue 9/166:00 amLEX - MDW
1 stop6h 48mDelta
Deal found 8/13$209
This Delta deal was found by Cheapflights users on 8/14. 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 8/276:17 pmMDW - LEX
1 stop3h 19mDelta
Sat 8/303:40 pmLEX - MDW
1 stop6h 32mDelta
Deal found 8/14$244
This Delta deal was found by Cheapflights users on 8/14. 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 8/226:17 pmMDW - LEX
1 stop3h 19mDelta
Sun 8/246:00 amLEX - MDW
1 stop4h 36mDelta
Deal found 8/14$269
This Delta deal was found by Cheapflights users on 8/11. 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 8/156:42 pmMDW - LEX
1 stop4h 08mDelta
Mon 8/185:54 pmLEX - MDW
1 stop4h 50mDelta
Deal found 8/11$301
This Delta deal was found by Cheapflights users on 8/13. 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 8/151:08 pmMDW - LEX
1 stop3h 02mDelta
Sat 8/163:40 pmLEX - MDW
1 stop6h 32mDelta
Deal found 8/13$304
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:46 pmMDW - LEX
1 stop14h 31mMultiple Airlines
Sun 10/59:41 pmLEX - MDW
1 stop10h 42mMultiple Airlines
Deal found 8/14$311
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:46 pmMDW - LEX
1 stop14h 31mAllegiant Air
Sun 10/57:25 pmLEX - MDW
2 stops22h 08mAllegiant Air
Deal found 8/14$322
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:48 amMDW - LEX
1 stop10h 11mMultiple Airlines
Sun 10/59:41 pmLEX - MDW
1 stop10h 42mMultiple Airlines
Deal found 8/12$326
This Delta deal was found by Cheapflights users on 8/12. 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 9/59:30 amMDW - LEX
1 stop7h 37mDelta
Mon 9/87:10 pmLEX - MDW
1 stop24h 27mDelta
Deal found 8/12$383
This Delta deal was found by Cheapflights users on 8/11. 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 8/281:08 pmMDW - LEX
1 stop3h 59mDelta
Mon 9/17:45 amLEX - MDW
1 stop5h 43mDelta
Deal found 8/11$384
This Delta deal was found by Cheapflights users on 8/12. 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 10/256:00 amMDW - LEX
1 stop5h 18mDelta
Mon 10/275:57 pmLEX - MDW
1 stop5h 17mDelta
Deal found 8/12$387
This Delta deal was found by Cheapflights users on 8/12. 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 9/41:08 pmMDW - LEX
1 stop3h 59mDelta
Mon 9/86:10 pmLEX - MDW
1 stop4h 16mDelta
Deal found 8/12$404

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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Lexington that are best for you.

Fly from

Midway

Fly to

Lexington

Route

Depart

Return

Price

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Mon 9/15

1:08 pm-5:08 pm

1 stop3h 00m

Lexington Blue Grass

Tue 9/16

6:00 am-11:48 am

1 stop6h 48m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 8/27

6:17 pm-10:36 pm

1 stop3h 19m

Lexington Blue Grass

Sat 8/30

3:40 pm-9:12 pm

1 stop6h 32m

$244

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 8/23

6:04 am-12:18 pm

1 stop5h 14m

Lexington Blue Grass

Sun 8/24

6:00 am-11:48 am

1 stop6h 48m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 8/22

6:42 pm-11:50 pm

1 stop4h 08m

Lexington Blue Grass

Sun 8/24

6:00 am-9:36 am

1 stop4h 36m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 9/26

9:48 am-8:15 pm

1 stop9h 27m

Lexington Blue Grass

Sun 9/28

4:36 pm-12:44 pm

1 stop21h 08m

$301

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Mon 8/18

6:17 pm-10:36 pm

1 stop3h 19m

Lexington Blue Grass

Sun 8/24

6:00 am-9:36 am

1 stop4h 36m

$301

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/2

4:46 pm-8:17 am

1 stop14h 31m

Lexington Blue Grass

Sun 10/5

9:41 pm-7:23 am

1 stop10h 42m

$311

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/2

4:46 pm-8:17 am

1 stop14h 31m

Lexington Blue Grass

Sun 10/5

7:25 pm-4:33 pm

2 stops22h 08m

$322

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 10/3

9:48 am-8:59 pm

1 stop10h 11m

Lexington Blue Grass

Sun 10/5

9:41 pm-7:23 am

1 stop10h 42m

$326

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 9/5

9:30 am-6:07 pm

1 stop7h 37m

Lexington Blue Grass

Mon 9/8

7:10 pm-6:37 pm

1 stop24h 27m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 20 results
1
2

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Lexington

What is the cheapest month to book a flight from Chicago Midway Airport to Lexington?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Lexington (average of $303). Flying from Chicago Midway Airport to Lexington in April is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Lexington?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Lexington (average of $303). Flying from Chicago Midway Airport to Lexington in April is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Lexington?

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