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$145+ Cheap flights from Lexington (LEX) to Midway (MDW)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — MDW
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Lexington to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Lexington (LEX) to Midway (MDW). 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 17, 2025.

Round-trip from

$209
(Delta)

One-way from

$145
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$281
From Lexington Blue Grass to Chicago Midway
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One-way flight from Lexington Blue Grass to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 Lexington to Midway

Cheapest flights from Lexington to Midway
Explore the most affordable flight options available from Lexington to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Delta deal was found by Cheapflights users on 8/16. 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 9/106:10 pmLEX - MDW
1 stop4h 16mDelta
Tue 9/166:00 amMDW - LEX
1 stop5h 15mDelta
Deal found 8/16$209
This Delta deal was found by Cheapflights users on 8/15. 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 9/37:45 amLEX - MDW
1 stop5h 43mDelta
Tue 9/94:25 pmMDW - LEX
1 stop6h 25mDelta
Deal found 8/15$214
This Delta deal was found by Cheapflights users on 8/15. 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 8/303:40 pmLEX - MDW
1 stop6h 32mDelta
Wed 9/36:17 pmMDW - LEX
1 stop3h 19mDelta
Deal found 8/15$227
This Delta deal was found by Cheapflights users on 8/15. 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 9/106:10 pmLEX - MDW
1 stop4h 16mDelta
Sat 9/131:08 pmMDW - LEX
1 stop3h 00mDelta
Deal found 8/15$234
This Delta deal was found by Cheapflights users on 8/15. 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 8/2710:24 amLEX - MDW
1 stop3h 04mDelta
Tue 9/26:17 pmMDW - LEX
1 stop3h 19mDelta
Deal found 8/15$244
This Delta deal was found by Cheapflights users on 8/16. 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 10/225:57 pmLEX - MDW
1 stop5h 17mDelta
Wed 10/296:00 amMDW - LEX
1 stop5h 18mDelta
Deal found 8/16$271
This Delta deal was found by Cheapflights users on 8/15. 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 8/217:45 amLEX - MDW
1 stop5h 43mDelta
Tue 9/26:17 pmMDW - LEX
1 stop3h 19mDelta
Deal found 8/15$276
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Sun 10/59:41 pmLEX - MDW
1 stop10h 42mMultiple Airlines
Fri 10/105:28 pmMDW - LEX
1 stop14h 39mMultiple Airlines
Deal found 8/16$283
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.
Thu 9/410:24 amLEX - MDW
1 stop3h 04mDelta
Tue 9/91:08 pmMDW - LEX
1 stop4h 01mDelta
Deal found 8/14$324
This Delta deal was found by Cheapflights users on 8/15. 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 9/117:55 amLEX - MDW
1 stop11h 40mDelta
Mon 9/156:30 pmMDW - LEX
1 stop4h 17mDelta
Deal found 8/15$332
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/39:49 pmLEX - MDW
1 stop13h 02mMultiple Airlines
Sun 10/510:13 amMDW - LEX
1 stop9h 38mMultiple Airlines
Deal found 8/16$361

Cheapflights Fare Finder

 
Customize your flight search to find flights from Lexington to Midway 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 17, 2025.
Use the filters below to find and compare flights from Lexington to Chicago Midway Airport that are best for you.

Fly from

Lexington

Fly to

Midway

Route

Depart

Return

Price

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 9/10

6:10 pm-9:26 pm

1 stop4h 16m

Chicago Midway

Tue 9/16

6:00 am-12:15 pm

1 stop5h 15m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 9/3

7:45 am-12:28 pm

1 stop5h 43m

Chicago Midway

Wed 9/10

6:00 am-12:18 pm

1 stop5h 18m

$214

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 9/3

7:45 am-12:28 pm

1 stop5h 43m

Chicago Midway

Tue 9/9

4:25 pm-11:50 pm

1 stop6h 25m

$214

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 8/30

3:40 pm-9:12 pm

1 stop6h 32m

Chicago Midway

Wed 9/3

6:17 pm-10:36 pm

1 stop3h 19m

$227

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 9/10

6:10 pm-9:26 pm

1 stop4h 16m

Chicago Midway

Sat 9/13

1:08 pm-5:08 pm

1 stop3h 00m

$234

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 8/27

10:24 am-12:28 pm

1 stop3h 04m

Chicago Midway

Tue 9/2

6:17 pm-10:36 pm

1 stop3h 19m

$244

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 11/20

7:30 am-12:32 pm

1 stop6h 02m

Chicago Midway

Thu 11/27

4:25 pm-10:30 pm

1 stop5h 05m

$271

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 10/22

5:57 pm-10:14 pm

1 stop5h 17m

Chicago Midway

Wed 10/29

6:00 am-12:18 pm

1 stop5h 18m

$271

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sun 10/5

9:41 pm-7:23 am

1 stop10h 42m

Chicago Midway

Fri 10/10

5:28 pm-9:07 am

1 stop14h 39m

$283

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 9/4

10:24 am-12:28 pm

1 stop3h 04m

Chicago Midway

Tue 9/9

1:08 pm-6:09 pm

1 stop4h 01m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 21 results
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Best time to book a flight from Lexington to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Lexington 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 Lexington to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $160). Flying from Lexington to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Lexington to Midway. 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 from for flights from Lexington to Chicago Midway?

    Most people fly from Lexington Blue Grass (LEX) if they book a flight from Lexington to Chicago Midway. On average, Blue Grass has 0 outbound flights to Chicago Midway per day from 0 airlines. Lexington Blue Grass is conveniently located just 5.6 mi from Lexington’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Lexington to Midway 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 Lexington to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $160). Flying from Lexington to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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