Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Lexington from $148

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Lexington departing on 11/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Lexington

Cheap round-trip flights

Delta Logo
1:14 pm - 5:32 pmMDW-LEX
3h 18m1 stop
Delta Logo
7:30 am - 12:34 pmLEX-MDW
6h 04m1 stop
$219Delta
Find Deal
Fri, Nov 21 - Sun, Nov 23
Delta Logo
11:00 am - 5:05 pmMDW-LEX
5h 05m1 stop
Delta Logo
5:56 pm - 9:36 pmLEX-MDW
4h 40m1 stop
$246Delta
Find Deal
Sat, Sep 20 - Mon, Sep 22
Delta Logo
6:00 am - 12:15 pmMDW-LEX
5h 15m1 stop
Delta Logo
6:15 pm - 9:36 pmLEX-MDW
4h 21m1 stop
$284Delta
Find Deal
Sat, Sep 20 - Wed, Oct 1
Delta Logo
4:23 pm - 12:04 amMDW-LEX
6h 41m1 stop
Delta Logo
5:57 pm - 10:14 pmLEX-MDW
5h 17m1 stop
$324Delta
Find Deal
Sat, Oct 25 - Mon, Oct 27
Logo
8:19 am - 8:59 pmMDW-LEX
11h 40m1 stop
Logo
3:38 pm - 9:47 amLEX-MDW
19h 09m1 stop
$373
Find Deal
Mon, Oct 6 - Wed, Oct 8
Logo
4:46 pm - 8:17 amMDW-LEX
14h 31m1 stop
Logo
9:41 pm - 7:23 amLEX-MDW
10h 42m1 stop
$375
Find Deal
Thu, Oct 2 - Sun, Oct 5
Logo
6:20 am - 6:35 pmMDW-LEX
11h 15m2 stops
Logo
9:41 pm - 7:23 amLEX-MDW
10h 42m1 stop
$378
Find Deal
Thu, Oct 2 - Sun, Oct 5
Logo
4:46 pm - 8:17 amMDW-LEX
14h 31m1 stop
Logo
3:52 pm - 7:11 amLEX-MDW
16h 19m2 stops
$402
Find Deal
Thu, Oct 2 - Sun, Oct 5
Allegiant Air Logo
4:46 pm - 8:17 amMDW-LEX
14h 31m1 stop
Allegiant Air Logo
7:25 pm - 4:33 pmLEX-MDW
22h 08m2 stops
$409Allegiant Air
Find Deal
Thu, Oct 2 - Sun, Oct 5
Allegiant Air Logo
2:11 pm - 12:12 pmMDW-LEX
21h 01m2 stops
Allegiant Air Logo
8:41 pm - 6:46 pmLEX-MDW
23h 05m2 stops
$580Allegiant Air
Find Deal
Fri, Nov 21 - Sun, Nov 23

Delta flights from Chicago Midway Airport to Lexington

Our best Delta deals on Chicago Midway Airport to Lexington flight tickets
Delta
Nov 21
MDW1:14 pmChicago Midway
3h 18m
1 stop
LEX5:32 pmLexington Blue Grass
Nov 23
LEX7:30 amLexington Blue Grass
6h 04m
1 stop
MDW12:34 pmChicago Midway
$219
Find similar
Delta
Sep 20
MDW11:00 amChicago Midway
5h 05m
1 stop
LEX5:05 pmLexington Blue Grass
Sep 22
LEX5:56 pmLexington Blue Grass
4h 40m
1 stop
MDW9:36 pmChicago Midway
$246
Find similar
Delta
Sep 20
MDW6:00 amChicago Midway
5h 15m
1 stop
LEX12:15 pmLexington Blue Grass
Oct 1
LEX6:15 pmLexington Blue Grass
4h 21m
1 stop
MDW9:36 pmChicago Midway
$284
Find similar

Allegiant Air flights from Chicago Midway Airport to Lexington

Our best Allegiant Air deals on Chicago Midway Airport to Lexington flight tickets
Allegiant Air
Oct 2
MDW4:46 pmChicago Midway
14h 31m
1 stop
LEX8:17 amLexington Blue Grass
Oct 5
LEX7:25 pmLexington Blue Grass
22h 08m
2 stops
MDW4:33 pmChicago Midway
$409
Find similar
Allegiant Air
Nov 21
MDW2:11 pmChicago Midway
21h 01m
2 stops
LEX12:12 pmLexington Blue Grass
Nov 23
LEX8:41 pmLexington Blue Grass
23h 05m
2 stops
MDW6:46 pmChicago Midway
$580
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Lexington that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 11/21

1:14 pm-5:32 pm

1 stop3h 18m

Lexington Blue Grass

Sun 11/23

7:30 am-12:34 pm

1 stop6h 04m

$219

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 9/20

11:00 am-5:05 pm

1 stop5h 05m

Lexington Blue Grass

Mon 9/22

5:56 pm-9:36 pm

1 stop4h 40m

$246

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 9/20

6:00 am-12:15 pm

1 stop5h 15m

Lexington Blue Grass

Wed 10/1

6:15 pm-9:36 pm

1 stop4h 21m

$284

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 10/25

4:23 pm-12:04 am

1 stop6h 41m

Lexington Blue Grass

Mon 10/27

5:57 pm-10:14 pm

1 stop5h 17m

$324

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Mon 10/6

8:19 am-8:59 pm

1 stop11h 40m

Lexington Blue Grass

Wed 10/8

3:38 pm-9:47 am

1 stop19h 09m

$373

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

$375

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/2

6:20 am-6:35 pm

2 stops11h 15m

Lexington Blue Grass

Sun 10/5

9:41 pm-7:23 am

1 stop10h 42m

$378

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/2

4:46 pm-8:17 am

1 stop14h 31m

Lexington Blue Grass

Sun 10/5

3:52 pm-7:11 am

2 stops16h 19m

$402

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/2

4:46 pm-8:17 am

1 stop14h 31m

Lexington Blue Grass

Sun 10/5

7:25 pm-4:33 pm

2 stops22h 08m

$409

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 11/21

2:11 pm-12:12 pm

2 stops21h 01m

Lexington Blue Grass

Sun 11/23

8:41 pm-6:46 pm

2 stops23h 05m

$580

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Lexington from

How to get the cheapest flight ticket from Chicago Midway Airport to Lexington

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Lexington?

On average, the least expensive day to fly to Lexington from Chicago Midway Airport is on a Saturday. momondo users have found tickets for Saturday departures for as low as $261. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Tuesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $288.

What is the cheapest time of day to depart on your flight to Lexington?

The cheapest time of day to fly to Lexington is in the afternoon when flights can be purchased for as low as $253. Try not to purchase tickets at noon because they tend to be around $288. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Chicago Midway Airport to Lexington

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Lexington according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Lexington (MDW to LEX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Lexington

Direct flights

None
There are no direct flights from Chicago Midway Airport to Lexington. There are no popular flight routes from Chicago Midway Airport to Lexington.
Search flight deals

  • How far is Chicago Midway to Lexington Blue Grass by plane?

    The straight-line distance from Chicago Midway to Lexington Blue Grass is 310.7 mi. 3h 00m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago Midway Airport to Lexington Blue Grass Airport?

    Prices for flights from Chicago Midway Airport to Lexington Blue Grass Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Lexington Blue Grass Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Lexington Blue Grass Airport.

  • What documentation or ID do you need to fly to Lexington Blue Grass Airport?

    The required travel and health documents for your Lexington Blue Grass Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Lexington Blue Grass Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Richmond
Somerset
Georgetown
Danville
Frankfort
Winchester
Berea
Carlisle
Versailles
Midway

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Lexington?

It is quick and easy to find Chicago to Lexington flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Lexington that suits you.

Can I find flights from Chicago to Lexington with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Lexington from Chicago with this policy.

How can momondo help me find flights from Chicago to Lexington?

momondo provides multiple filters to help you find the best flight to Lexington from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Lexington right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Lexington flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Lexington trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 9/2
Tue 9/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States