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$141+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — MDW
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Delta)

One-way from

$141
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$294
Provider with most accurate pricing for Lexington Blue Grass-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Lexington Blue Grass-Chicago Midway flights.
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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. 1% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 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 November 2, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 12/177:45 amLEX - MDW
1 stop5h 49mDelta
Wed 12/243:29 pmMDW - LEX
1 stop6h 16mDelta
Deal found 10/30$209
This Delta deal was found by Cheapflights users on 11/2. 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 11/217:59 pmLEX - MDW
1 stop4h 41mDelta
Sat 11/224:28 pmMDW - LEX
1 stop6h 28mDelta
Deal found 11/2$239
This Delta deal was found by Cheapflights users on 10/31. 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 12/126:05 amLEX - MDW
1 stop6h 50mDelta
Sun 12/145:13 pmMDW - LEX
1 stop5h 55mDelta
Deal found 10/31$242
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/173:01 pmLEX - MDW
1 stop19h 22mMultiple Airlines
Wed 12/246:12 amMDW - LEX
2 stops30h 16mMultiple Airlines
Deal found 11/1$245
This Delta deal was found by Cheapflights users on 10/31. 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 12/77:59 pmLEX - MDW
1 stop4h 48mDelta
Sat 12/131:14 pmMDW - LEX
1 stop3h 17mDelta
Deal found 10/31$284
This Delta deal was found by Cheapflights users on 10/31. 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 11/47:45 amLEX - MDW
1 stop5h 43mDelta
Sat 11/810:35 amMDW - LEX
1 stop5h 37mDelta
Deal found 10/31$302
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/173:01 pmLEX - MDW
1 stop19h 22mAllegiant Air
Tue 12/239:43 amMDW - LEX
1 stop28h 14mAllegiant Air
Deal found 10/30$309
This Delta deal was found by Cheapflights users on 10/31. 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.
Mon 11/35:57 pmLEX - MDW
1 stop5h 17mDelta
Sat 11/86:00 amMDW - LEX
1 stop5h 18mDelta
Deal found 10/31$331
This Delta deal was found by Cheapflights users on 10/31. 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.
Mon 12/157:45 amLEX - MDW
1 stop5h 49mDelta
Mon 12/226:08 pmMDW - LEX
1 stop3h 59mDelta
Deal found 10/31$364
This Delta deal was found by Cheapflights users on 10/31. 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 12/197:45 amLEX - MDW
1 stop5h 49mDelta
Mon 12/226:08 pmMDW - LEX
1 stop3h 59mDelta
Deal found 10/31$439
This Delta deal was found by Cheapflights users on 11/2. 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 11/256:00 amLEX - MDW
1 stop4h 52mDelta
Tue 11/255:34 pmMDW - LEX
1 stop5h 30mDelta
Deal found 11/2$447

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 November 2, 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

Fri 2/13

6:00 am-9:58 am

1 stop4h 58m

Chicago Midway

Sun 2/15

6:00 am-12:50 pm

1 stop5h 50m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 12/17

7:45 am-12:34 pm

1 stop5h 49m

Chicago Midway

Wed 12/24

6:08 pm-11:07 pm

1 stop3h 59m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 2/28

7:26 am-12:48 pm

1 stop6h 22m

Chicago Midway

Tue 3/3

6:00 am-12:50 pm

1 stop5h 50m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 11/21

7:59 pm-11:40 pm

1 stop4h 41m

Chicago Midway

Sat 11/22

4:28 pm-11:56 pm

1 stop6h 28m

$239

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 12/20

6:20 am-8:49 am

1 stop3h 29m

Chicago Midway

Sat 12/27

6:00 am-12:36 pm

1 stop5h 36m

$242

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 12/5

7:45 am-12:34 pm

1 stop5h 49m

Chicago Midway

Sun 12/7

12:50 pm-7:08 pm

1 stop5h 18m

$242

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 12/12

6:05 am-11:55 am

1 stop6h 50m

Chicago Midway

Sun 12/14

5:13 pm-12:08 am

1 stop5h 55m

$242

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 12/17

3:01 pm-9:23 am

1 stop19h 22m

Chicago Midway

Wed 12/24

6:12 am-1:28 pm

2 stops30h 16m

$245

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 2/28

7:26 am-12:48 pm

1 stop6h 22m

Chicago Midway

Mon 3/2

12:46 pm-6:53 pm

1 stop5h 07m

$284

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 2/5

7:26 am-12:48 pm

1 stop6h 22m

Chicago Midway

Mon 2/9

9:34 am-4:55 pm

1 stop6h 21m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 18 results
1
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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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 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 Lexington-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Lexington-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 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 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, January is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $73). Flying from Lexington to Chicago Midway Airport in May is currently the most expensive (average of $192). 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 4h 58m. 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, January is the cheapest month in which you can book a flight from Lexington to Chicago Midway Airport (average of $73). Flying from Lexington to Chicago Midway Airport in May is currently the most expensive (average of $192). 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
Porter
Benton Harbor

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