$217 Cheap Flights from Lexington (LEX) to Chicago (MDW)

View $217 flight on Tue, Nov 18, 2025Opens in a new window

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

Cheap Flights from Lexington to Chicago (LEX-MDW)

Prices were available within the past 7 days and start at $217 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 8
LEX
Lexington
MDW
Chicago
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Nov 24 from Lexington to Chicago, returning Mon, Dec 8, priced at $209 found 2 hours ago
Delta
Sat, Oct 18 - Fri, Oct 31
LEX
Lexington
MDW
Chicago
$214 Roundtrip, found 18 hours ago
$214
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Oct 18 from Lexington to Chicago, returning Fri, Oct 31, priced at $214 found 18 hours ago
Delta
Sat, Oct 18 - Tue, Oct 21
LEX
Lexington
MDW
Chicago
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 18 from Lexington to Chicago, returning Tue, Oct 21, priced at $219 found 1 day ago
Delta
Sat, Aug 15 - Sat, Aug 22
LEX
Lexington
MDW
Chicago
$222 Roundtrip, found 3 hours ago
$222
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Aug 15 from Lexington to Chicago, returning Sat, Aug 22, priced at $222 found 3 hours ago
Delta
Wed, Oct 29 - Sat, Nov 1
LEX
Lexington
MDW
Chicago
$234 Roundtrip, found 1 hour ago
$234
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Oct 29 from Lexington to Chicago, returning Sat, Nov 1, priced at $234 found 1 hour ago
Delta
Wed, Nov 26 - Tue, Dec 2
LEX
Lexington
MDW
Chicago
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 26 from Lexington to Chicago, returning Tue, Dec 2, priced at $235 found 2 days ago
Delta
Sat, Oct 18 - Sun, Oct 26
LEX
Lexington
MDW
Chicago
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 18 from Lexington to Chicago, returning Sun, Oct 26, priced at $239 found 1 day ago
Delta
Wed, Oct 8 - Sat, Oct 25
LEX
Lexington
MDW
Chicago
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 8 from Lexington to Chicago, returning Sat, Oct 25, priced at $242 found 1 day ago
Delta
Wed, Oct 15 - Mon, Oct 20
LEX
Lexington
MDW
Chicago
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Oct 15 from Lexington to Chicago, returning Mon, Oct 20, priced at $244 found 3 days ago
Delta
Sat, Mar 7 - Mon, Mar 16
LEX
Lexington
MDW
Chicago
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Mar 7 from Lexington to Chicago, returning Mon, Mar 16, priced at $247 found 3 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $199
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $199

Frequently asked questions

How much does a flight from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $217 or cheap return flight from $209 from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW) 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 Blue Grass Airport (LEX) to Midway Intl. Airport (MDW)?
November is the most affordable month to fly from LEX to MDW. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from LEX to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from LEX to MDW?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change based on the season, 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 Blue Grass Airport (LEX) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Blue Grass Airport (LEX) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later flights have a 22% higher chance of being canceled.**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.
What airports do you fly into for Chicago from Blue Grass Airport (LEX)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Blue Grass Airport (LEX). Compare your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from LEX to MDW are typically more expensive. To secure the lowest prices, start looking for flights as early as possible. That being said, if your travel plans are flexible, you may score a cheap fare just before your departure.
Is it cheaper to book a LEX to MDW flight and hotel package?
You can save money by booking a LEX to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After selecting your ideal flights and accommodations, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Blue Grass Airport (LEX) to Midway Intl. Airport (MDW)?
It's usually possible to cancel or reschedule your LEX to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Blue Grass
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$208
Distance
307 mi

Book with confidence

Book with confidence

Lexington to Chicago Flights

The cheapest times to fly from Lexington to Chicago

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 Lexington to Chicago are during the month of November. You can find some of the cheapest flights from Lexington to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Lexington to Chicago

Sunday is one of the best days to book for cheap flights from Lexington to Chicago: 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 Lexington to Chicago

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 Lexington to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $217 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 Lexington to Chicago 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 Lexington to Chicago 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.

 

Lexington to Chicago Flights

Explore a world of travel with Expedia

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*Available to One Key members.