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$148+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LEX
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Delta)

One-way from

$148
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$327
Provider with most accurate pricing for Chicago Midway-Lexington Blue Grass flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Lexington Blue Grass flights.
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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. 14% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 13, 2025.

This Delta deal was found by Cheapflights users on 11/13. 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.
Thu 12/46:00 amMDW - LEX
1 stop5h 23mDelta
Sun 12/76:05 amLEX - MDW
1 stop6h 50mDelta
Deal found 11/13$209
This Delta deal was found by Cheapflights users on 11/11. 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 12/121:14 pmMDW - LEX
1 stop3h 07mDelta
Sun 12/147:45 amLEX - MDW
1 stop5h 49mDelta
Deal found 11/11$224
This Delta deal was found by Cheapflights users on 11/12. 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 12/276:08 pmMDW - LEX
1 stop3h 59mDelta
Sat 1/36:20 amLEX - MDW
1 stop3h 29mDelta
Deal found 11/12$242
This Delta deal was found by Cheapflights users on 11/12. 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.
Sun 12/216:08 pmMDW - LEX
1 stop3h 59mDelta
Sun 1/46:20 amLEX - MDW
1 stop3h 29mDelta
Deal found 11/12$257
This Delta deal was found by Cheapflights users on 11/11. 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 11/215:34 pmMDW - LEX
1 stop5h 30mDelta
Mon 11/246:00 amLEX - MDW
1 stop6h 52mDelta
Deal found 11/11$267
This Delta deal was found by Cheapflights users on 11/11. 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 11/1410:47 amMDW - LEX
1 stop5h 08mDelta
Tue 11/187:45 amLEX - MDW
1 stop5h 49mDelta
Deal found 11/11$331
This Delta deal was found by Cheapflights users on 11/11. 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 11/145:34 pmMDW - LEX
1 stop5h 30mDelta
Sat 11/155:39 pmLEX - MDW
1 stop7h 01mDelta
Deal found 11/11$334
This Delta deal was found by Cheapflights users on 11/12. 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 11/1412:47 pmMDW - LEX
1 stop5h 27mDelta
Mon 11/175:40 pmLEX - MDW
1 stop7h 00mDelta
Deal found 11/12$363
This Delta deal was found by Cheapflights users on 11/11. 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 12/191:14 pmMDW - LEX
1 stop3h 07mDelta
Mon 12/226:20 amLEX - MDW
1 stop3h 29mDelta
Deal found 11/11$397
This Delta deal was found by Cheapflights users on 11/10. 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 12/91:14 pmMDW - LEX
1 stop3h 07mDelta
Fri 12/127:45 amLEX - MDW
1 stop5h 49mDelta
Deal found 11/10$447
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/212:11 pmMDW - LEX
2 stops21h 01mAllegiant Air
Mon 11/248:57 pmLEX - MDW
1 stop13h 35mAllegiant Air
Deal found 11/11$487
This Delta deal was found by Cheapflights users on 11/12. 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.
Wed 11/261:15 pmMDW - LEX
1 stop3h 17mDelta
Sat 11/296:00 amLEX - MDW
1 stop4h 52mDelta
Deal found 11/12$494

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 November 13, 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

Sat 12/6

1:14 pm-5:31 pm

1 stop3h 17m

Lexington Blue Grass

Mon 12/8

7:59 pm-11:47 pm

1 stop4h 48m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 12/4

5:13 pm-12:08 am

1 stop5h 55m

Lexington Blue Grass

Wed 12/10

7:10 am-11:55 am

1 stop5h 45m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 12/4

6:00 am-12:23 pm

1 stop5h 23m

Lexington Blue Grass

Sun 12/7

6:05 am-11:55 am

1 stop6h 50m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 2/5

9:34 am-4:55 pm

1 stop6h 21m

Lexington Blue Grass

Sun 2/8

7:26 am-12:48 pm

1 stop6h 22m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 12/12

1:14 pm-5:21 pm

1 stop3h 07m

Lexington Blue Grass

Sun 12/14

7:45 am-12:34 pm

1 stop5h 49m

$224

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 12/27

6:08 pm-11:07 pm

1 stop3h 59m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$242

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sun 12/28

6:08 pm-11:07 pm

1 stop3h 59m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$242

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sun 12/21

6:08 pm-11:07 pm

1 stop3h 59m

Lexington Blue Grass

Sun 1/4

6:20 am-8:49 am

1 stop3h 29m

$257

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 2/5

10:17 am-8:44 am

1 stop21h 27m

Lexington Blue Grass

Sun 2/8

11:51 am-10:19 pm

2 stops11h 28m

$264

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 12/19

1:14 pm-5:21 pm

1 stop3h 07m

Lexington Blue Grass

Mon 12/22

6:20 am-8:49 am

1 stop3h 29m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 20 results
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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Lexington flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Lexington (average of $124). Flying from Chicago Midway Airport to Lexington in March is currently the most expensive (average of $404). 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.

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

    For as low as $209, Delta can have you in Lexington from Chicago Midway Airport in 3h 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.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Lexington (average of $124). Flying from Chicago Midway Airport to Lexington in March is currently the most expensive (average of $404). 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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