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$147+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$209
(Delta)

One-way from

$147
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$261
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 ($8 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 September 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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 12/65:35 pmLEX - MDW
1 stop6h 57mDelta
Mon 12/81:14 pmMDW - LEX
1 stop3h 17mDelta
Deal found 9/14$209
This Delta deal was found by Cheapflights users on 9/15. 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 10/187:45 amLEX - MDW
1 stop5h 46mDelta
Mon 10/205:04 pmMDW - LEX
1 stop6h 00mDelta
Deal found 9/15$271
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 9/166:00 amLEX - MDW
1 stop4h 40mDelta
Tue 9/236:00 amMDW - LEX
1 stop5h 15mDelta
Deal found 9/15$272
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 11/17:45 amLEX - MDW
1 stop5h 46mDelta
Mon 11/310:30 amMDW - LEX
1 stop5h 42mDelta
Deal found 9/14$324
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/175:20 pmLEX - MDW
1 stop5h 54mDelta
Sat 10/186:00 amMDW - LEX
1 stop5h 18mDelta
Deal found 9/16$333
This Delta deal was found by Cheapflights users on 9/16. 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 10/17:55 amLEX - MDW
1 stop5h 33mDelta
Sun 10/126:00 amMDW - LEX
1 stop5h 18mDelta
Deal found 9/16$378
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 9/2010:24 amLEX - MDW
1 stop3h 04mDelta
Sun 9/286:00 amMDW - LEX
1 stop5h 15mDelta
Deal found 9/16$379
This Mytrip deal was found by Cheapflights users on 9/17. 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 10/164:19 pmLEX - MDW
2 stops19h 57mAllegiant Air
Fri 10/175:24 pmMDW - LEX
2 stops13h 34mAllegiant Air
Deal found 9/17$380
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 9/195:56 pmLEX - MDW
1 stop4h 40mDelta
Wed 9/246:00 amMDW - LEX
1 stop5h 15mDelta
Deal found 9/15$414
This Delta deal was found by Cheapflights users on 9/17. 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 9/246:15 pmLEX - MDW
1 stop4h 21mDelta
Sat 9/2711:00 amMDW - LEX
1 stop5h 05mDelta
Deal found 9/17$439
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/111:29 amLEX - MDW
1 stop29h 27mAllegiant Air
Sun 10/54:46 pmMDW - LEX
1 stop26h 23mAllegiant Air
Deal found 9/16$442

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 September 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

Thu 3/12

7:30 am-12:35 pm

1 stop6h 05m

Chicago Midway

Mon 3/16

1:00 pm-5:13 pm

1 stop3h 13m

$234

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 10/18

7:45 am-12:31 pm

1 stop5h 46m

Chicago Midway

Mon 10/20

5:04 pm-12:04 am

1 stop6h 00m

$271

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 11/14

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Sat 11/15

11:05 am-4:40 pm

1 stop4h 35m

$271

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 11/6

7:45 am-12:28 pm

1 stop5h 43m

Chicago Midway

Sun 11/9

1:14 pm-5:32 pm

1 stop3h 18m

$271

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 3/14

5:49 pm-9:46 pm

1 stop4h 57m

Chicago Midway

Sat 3/21

1:00 pm-5:13 pm

1 stop3h 13m

$284

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 11/1

7:45 am-12:31 pm

1 stop5h 46m

Chicago Midway

Mon 11/3

10:30 am-5:12 pm

1 stop5h 42m

$324

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 10/17

5:20 pm-10:14 pm

1 stop5h 54m

Chicago Midway

Sat 10/18

6:00 am-12:18 pm

1 stop5h 18m

$333

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 10/23

10:25 am-12:28 pm

1 stop3h 03m

Chicago Midway

Mon 10/27

1:08 pm-5:14 pm

1 stop3h 06m

$379

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 3/13

5:49 pm-9:46 pm

1 stop4h 57m

Chicago Midway

Mon 3/16

1:00 pm-5:13 pm

1 stop3h 13m

$379

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 10/1

7:55 am-12:28 pm

1 stop5h 33m

Chicago Midway

Sun 10/12

6:00 am-12:18 pm

1 stop5h 18m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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.

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

    For as low as $234, Delta can have you in Chicago Midway Airport from Lexington in 6h 05m. Airlines will cover a distance of 308 mi.

  • 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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