HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Lexington

$147+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LEX
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Lexington with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Delta)

One-way from

$147
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$316
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. 10% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 25, 2025.

This Delta deal was found by Cheapflights users on 9/23. 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 11/811:10 amMDW - LEX
1 stop4h 58mDelta
Sun 11/98:07 pmLEX - MDW
1 stop4h 33mDelta
Deal found 9/23$209
This Delta deal was found by Cheapflights users on 9/24. 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 11/196:00 amMDW - LEX
1 stop5h 20mDelta
Sun 11/236:00 amLEX - MDW
1 stop4h 52mDelta
Deal found 9/24$333
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/64:33 pmMDW - LEX
1 stop21h 37mMultiple Airlines
Sun 11/910:05 pmLEX - MDW
2 stops14h 25mMultiple Airlines
Deal found 9/25$364
This Mytrip deal was found by Cheapflights users on 9/25. 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.
Fri 10/175:24 pmMDW - LEX
2 stops13h 34mAllegiant Air
Sun 10/197:25 pmLEX - MDW
2 stops22h 08mAllegiant Air
Deal found 9/25$384
This Delta deal was found by Cheapflights users on 9/24. 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 10/114:23 pmMDW - LEX
1 stop6h 41mDelta
Mon 10/135:57 pmLEX - MDW
1 stop5h 17mDelta
Deal found 9/24$389
This Delta deal was found by Cheapflights users on 9/24. 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 10/306:00 amMDW - LEX
1 stop5h 18mDelta
Mon 11/37:45 amLEX - MDW
1 stop5h 43mDelta
Deal found 9/24$398
This Delta deal was found by Cheapflights users on 9/25. 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 11/610:40 amMDW - LEX
1 stop5h 32mDelta
Sun 11/98:07 pmLEX - MDW
1 stop4h 33mDelta
Deal found 9/25$404
This Delta deal was found by Cheapflights users on 9/24. 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 10/114:23 pmMDW - LEX
1 stop6h 41mDelta
Tue 10/145:57 pmLEX - MDW
1 stop5h 17mDelta
Deal found 9/24$419
This Delta deal was found by Cheapflights users on 9/23. 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 12/21:14 pmMDW - LEX
1 stop3h 17mDelta
Wed 12/37:15 amLEX - MDW
1 stop5h 40mDelta
Deal found 9/23$447
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 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 10/510:33 pmLEX - MDW
2 stops18h 52mMultiple Airlines
Deal found 9/23$450
This Delta deal was found by Cheapflights users on 9/24. 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 10/2310:35 amMDW - LEX
1 stop5h 37mDelta
Mon 10/275:57 pmLEX - MDW
2 stops24h 46mDelta
Deal found 9/24$466

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 September 25, 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 11/8

11:10 am-5:08 pm

1 stop4h 58m

Lexington Blue Grass

Sun 11/9

8:07 pm-11:40 pm

1 stop4h 33m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 11/19

6:00 am-12:20 pm

1 stop5h 20m

Lexington Blue Grass

Sun 11/23

6:00 am-9:52 am

1 stop4h 52m

$333

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/30

6:00 am-12:18 pm

1 stop5h 18m

Lexington Blue Grass

Mon 11/3

7:45 am-12:28 pm

1 stop5h 43m

$398

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 11/6

10:40 am-5:12 pm

1 stop5h 32m

Lexington Blue Grass

Sun 11/9

8:07 pm-11:40 pm

1 stop4h 33m

$404

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 11/7

5:09 pm-12:05 am

1 stop5h 56m

Lexington Blue Grass

Sun 11/9

8:07 pm-11:40 pm

1 stop4h 33m

$404

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 10/11

4:23 pm-12:04 am

1 stop6h 41m

Lexington Blue Grass

Tue 10/14

5:57 pm-10:14 pm

1 stop5h 17m

$419

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 12/2

1:14 pm-5:31 pm

1 stop3h 17m

Lexington Blue Grass

Wed 12/3

7:15 am-11:55 am

1 stop5h 40m

$447

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/23

10:35 am-5:12 pm

1 stop5h 37m

Lexington Blue Grass

Mon 10/27

5:57 pm-5:43 pm

2 stops24h 46m

$466

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

$472

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 10/3

6:30 pm-11:47 pm

1 stop4h 17m

Lexington Blue Grass

Sat 10/4

10:26 am-3:26 pm

1 stop6h 00m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 21 results
1
2
3

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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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.

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.

  • 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 4h 58m. 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, 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?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.