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$155+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 4/167:30 am
LEX
-
MDW
1 stop6h 13m
Delta
Tue 4/216:00 am
MDW
-
LEX
1 stop6h 34m
Delta
Deal found 1/28$209
This Delta deal was found by Cheapflights users on 1/28. 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 3/147:45 am
LEX
-
MDW
1 stop5h 44m
Delta
Tue 3/1712:47 pm
MDW
-
LEX
1 stop5h 23m
Delta
Deal found 1/28$224
This Delta deal was found by Cheapflights users on 1/27. 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 2/255:47 pm
LEX
-
MDW
1 stop5h 44m
Delta
Sat 2/289:34 am
MDW
-
LEX
1 stop6h 19m
Delta
Deal found 1/27$284
This Delta deal was found by Cheapflights users on 1/28. 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 4/187:30 am
LEX
-
MDW
1 stop6h 13m
Delta
Sat 4/186:38 pm
MDW
-
LEX
1 stop14h 30m
Delta
Deal found 1/28$294
This Delta deal was found by Cheapflights users on 1/28. 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 4/37:45 am
LEX
-
MDW
1 stop5h 44m
Delta
Sun 4/56:00 am
MDW
-
LEX
1 stop4h 54m
Delta
Deal found 1/28$314
This Delta deal was found by Cheapflights users on 1/28. 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 4/167:30 am
LEX
-
MDW
1 stop6h 13m
Delta
Fri 4/176:38 pm
MDW
-
LEX
1 stop14h 30m
Delta
Deal found 1/28$326
This Delta deal was found by Cheapflights users on 1/28. 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 4/1512:44 pm
LEX
-
MDW
1 stop4h 45m
Delta
Thu 4/236:00 am
MDW
-
LEX
1 stop4h 46m
Delta
Deal found 1/28$334
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/229:35 am
LEX
-
MDW
2 stops13h 44m
Multiple Airlines
Tue 3/244:33 pm
MDW
-
LEX
1 stop26h 03m
Multiple Airlines
Deal found 1/28$339
This Delta deal was found by Cheapflights users on 1/27. 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 2/66:40 pm
LEX
-
MDW
1 stop4h 42m
Delta
Mon 2/99:33 am
MDW
-
LEX
1 stop6h 17m
Delta
Deal found 1/27$341
This Delta deal was found by Cheapflights users on 1/28. 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 4/167:30 am
LEX
-
MDW
1 stop6h 13m
Delta
Sun 4/191:23 pm
MDW
-
LEX
1 stop7h 37m
Delta
Deal found 1/28$345
This Delta deal was found by Cheapflights users on 1/28. 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 2/127:26 am
LEX
-
MDW
1 stop6h 20m
Delta
Mon 2/166:40 pm
MDW
-
LEX
1 stop4h 08m
Delta
Deal found 1/28$349
This Delta deal was found by Cheapflights users on 1/27. 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 1/285:00 pm
LEX
-
MDW
1 stop6h 22m
Delta
Mon 2/212:46 pm
MDW
-
LEX
1 stop4h 05m
Delta
Deal found 1/27$354

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Delta)

One-way from

$155
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$268
Provider with most accurate pricing for Lexington Blue Grass-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lexington Blue Grass-Chicago Midway flights.
Search Deals
From Lexington Blue Grass to Chicago Midway
Search Deals
One-way flight from Lexington Blue Grass to Chicago Midway
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Fri 2/20

7:26 am-12:46 pm

1 stop6h 20m

Chicago Midway

Sun 2/22

9:34 am-4:51 pm

1 stop6h 17m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/15

12:44 pm-4:29 pm

1 stop4h 45m

Chicago Midway

Tue 4/21

6:00 am-1:34 pm

1 stop6h 34m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 4/17

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Mon 4/20

6:00 am-1:34 pm

1 stop6h 34m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/16

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Mon 4/20

6:00 am-1:34 pm

1 stop6h 34m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/15

12:44 pm-4:29 pm

1 stop4h 45m

Chicago Midway

Sat 4/18

6:00 am-11:46 am

1 stop4h 46m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 4/18

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Wed 4/22

6:00 am-11:46 am

1 stop4h 46m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/16

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Tue 4/21

6:00 am-1:34 pm

1 stop6h 34m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/16

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Sat 4/18

6:00 am-11:46 am

1 stop4h 46m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 2/18

7:26 am-12:46 pm

1 stop6h 20m

Chicago Midway

Sat 2/21

9:34 am-4:53 pm

1 stop6h 19m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/15

4:53 pm-10:28 pm

1 stop6h 35m

Chicago Midway

Wed 4/22

6:00 am-11:46 am

1 stop4h 46m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 21 results
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Compare providers for flights from Lexington to Midway

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 Lexington to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Lexington-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Lexington-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Lexington-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Lexington-Chicago Midway Airport 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 Lexington-Chicago Midway Airport 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 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, September is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $77). Flying from Lexington to Chicago Midway Airport in November is currently the most expensive (average of $251). 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 $209, Delta can have you in Chicago Midway Airport from Lexington in 6h 20m. 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, September is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $77). Flying from Lexington to Chicago Midway Airport in November is currently the most expensive (average of $251). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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