$192 Cheap Flights from Chicago (MDW) to Lexington (LEX)

View $192 flight on Fri, Dec 5, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Blue Grass Airport (LEX)

Cheap Flights from Chicago to Lexington (MDW-LEX)

Prices were available within the past 7 days and start at $192 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Nov 24 - Mon, Dec 1
MDW
Chicago
LEX
Lexington
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Nov 24 from Chicago to Lexington, returning Mon, Dec 1, priced at $209 found 1 hour ago
Delta
Wed, Apr 1 - Tue, Apr 14
MDW
Chicago
LEX
Lexington
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Lexington, returning Tue, Apr 14, priced at $222 found 2 days ago
Delta
Fri, Nov 21 - Sun, Nov 23
MDW
Chicago
LEX
Lexington
$224 Roundtrip, found 4 hours ago
$224
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Nov 21 from Chicago to Lexington, returning Sun, Nov 23, priced at $224 found 4 hours ago
Delta
Thu, Jan 22 - Sun, Feb 8
MDW
Chicago
LEX
Lexington
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Jan 22 from Chicago to Lexington, returning Sun, Feb 8, priced at $234 found 4 days ago
Delta
Fri, Nov 21 - Sun, Nov 23
MDW
Chicago
LEX
Lexington
$239 Roundtrip, found 4 hours ago
$239
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Nov 21 from Chicago to Lexington, returning Sun, Nov 23, priced at $239 found 4 hours ago
Delta
Mon, Mar 9 - Mon, Mar 23
MDW
Chicago
LEX
Lexington
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Mar 9 from Chicago to Lexington, returning Mon, Mar 23, priced at $242 found 2 days ago
Delta
Tue, Dec 2 - Fri, Dec 19
MDW
Chicago
LEX
Lexington
$247 Roundtrip, found 4 days ago
$247
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Lexington, returning Fri, Dec 19, priced at $247 found 4 days ago
Delta
Wed, Dec 10 - Mon, Dec 15
MDW
Chicago
LEX
Lexington
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 10 from Chicago to Lexington, returning Mon, Dec 15, priced at $247 found 1 day ago
Delta
Sat, Nov 15 - Sat, Nov 22
MDW
Chicago
LEX
Lexington
$254 Roundtrip, found 5 hours ago
$254
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Nov 15 from Chicago to Lexington, returning Sat, Nov 22, priced at $254 found 5 hours ago
Delta
Wed, Apr 1 - Thu, Apr 16
MDW
Chicago
LEX
Lexington
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Lexington, returning Thu, Apr 16, priced at $255 found 2 days ago

Alternative airports near Lexington

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Blue Grass LEX. Cheapest and Closest option available. Average driving time to city center is 9 minutes. Flights from $286
LEX
Blue Grass
CheapestClosest
Average driving time to city center9 min
Flights from $286
Flights from Chicago (MDW) to Lexington (LEX)
Origin airport
Midway Intl.
Destination airport
Blue Grass
Airlines serving
Delta
Roundtrip price
$208
Distance
307 mi

Chicago to Lexington Flights

The cheapest times to fly from Chicago to Lexington

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Lexington are during the month of November. You can find some of the cheapest flights from Chicago to Lexington with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Lexington

Sunday is one of the best days to book for cheap flights from Chicago to Lexington: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Lexington

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Lexington in 2025. You can also book with separate airlines for your outbound and return journeys, from $192 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Lexington flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Lexington airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX) cost?
Get a cheap one-way flight from $192 or cheap return flight from $209 from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
Planning your getaway for November is a great way to save, as it's the cheapest month for flights between MDW and LEX. You'll often find the lowest fares during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
While Chicago, IL (MDW-Midway Intl.) has no direct flights to Blue Grass Airport (LEX), other airports have nonstop routes. Leaving from O'Hare Intl. Airport (ORD) will get you to Lexington without any layovers.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from MDW to LEX. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
You'll need to catch a flight with a layover when traveling from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from MDW to LEX?
Typically you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* However, this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
To arrive at Blue Grass Airport (LEX) without delays, pick a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX) last-minute?
Waiting until just before your trip to book your flight from MDW to LEX generally means paying more. While it's possible to find some last-minute deals, they're not always guaranteed. Be flexible with your itinerary to boost your chances of getting a bargain.
Is it cheaper to book a MDW to LEX flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to LEX flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one convenient place will take the stress out of planning your trip. Just secure your flights and choose from our wide range of stays, then tailor your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Blue Grass Airport (LEX)?
In most cases, you can reschedule or cancel your MDW to LEX flight. However, there may be additional fees, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you want further details, go to our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.