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Cheap flights from Chicago Midway Airport to Lexington from $162

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 10/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Lexington

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:23 pm - 12:05 amMDW-LEX
6h 42m1 stop
Delta Logo
6:00 am - 9:53 amLEX-MDW
4h 53m1 stop
$209Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
6:00 am - 12:21 pmMDW-LEX
5h 21m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$222Delta
Find Deal
Wed, Dec 10 - Sat, Jan 3
Delta Logo
6:00 am - 12:21 pmMDW-LEX
5h 21m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$234Delta
Find Deal
Thu, Dec 11 - Sun, Jan 4
Delta Logo
6:00 am - 12:21 pmMDW-LEX
5h 21m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$247Delta
Find Deal
Thu, Dec 11 - Sat, Jan 3
Delta Logo
5:38 pm - 12:08 amMDW-LEX
5h 30m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$271Delta
Find Deal
Wed, Dec 10 - Sat, Jan 3
Delta Logo
1:14 pm - 5:21 pmMDW-LEX
3h 07m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$284Delta
Find Deal
Fri, Dec 12 - Sat, Jan 3
Multiple Airlines Logo
6:40 pm - 3:20 pmMDW-LEX
19h 40m1 stop
Multiple Airlines Logo
9:41 pm - 8:32 amLEX-MDW
11h 51m1 stop
$289Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
6:46 pm - 9:52 amMDW-LEX
14h 06m1 stop
Delta Logo
6:20 am - 8:49 amLEX-MDW
3h 29m1 stop
$297Delta
Find Deal
Sat, Dec 13 - Sat, Jan 3
Delta Logo
6:00 am - 12:18 pmMDW-LEX
5h 18m1 stop
Delta Logo
3:46 pm - 10:14 pmLEX-MDW
7h 28m1 stop
$301Delta
Find Deal
Tue, Oct 28 - Sat, Nov 1
Multiple Airlines Logo
6:40 pm - 3:20 pmMDW-LEX
19h 40m1 stop
Multiple Airlines Logo
10:19 pm - 4:52 pmLEX-MDW
19h 33m2 stops
$340Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2

Delta flights from Chicago Midway Airport to Lexington

Our best Delta deals on Chicago Midway Airport to Lexington flight tickets
Delta
Nov 8
MDW4:23 pmChicago Midway
6h 42m
1 stop
LEX12:05 amLexington Blue Grass
Nov 15
LEX6:00 amLexington Blue Grass
4h 53m
1 stop
MDW9:53 amChicago Midway
$209
Find similar
Delta
Dec 10
MDW6:00 amChicago Midway
5h 21m
1 stop
LEX12:21 pmLexington Blue Grass
Jan 3
LEX6:20 amLexington Blue Grass
3h 29m
1 stop
MDW8:49 amChicago Midway
$222
Find similar
Delta
Dec 11
MDW6:00 amChicago Midway
5h 21m
1 stop
LEX12:21 pmLexington Blue Grass
Jan 4
LEX6:20 amLexington Blue Grass
3h 29m
1 stop
MDW8:49 amChicago Midway
$234
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 17
MDW5:24 pmChicago Midway
13h 34m
2 stops
LEX7:58 amLexington Blue Grass
Oct 19
LEX7:25 pmLexington Blue Grass
22h 08m
2 stops
MDW4:33 pmChicago Midway
$532
Find similar
Allegiant Air
Oct 17
MDW5:24 pmChicago Midway
13h 34m
2 stops
LEX7:58 amLexington Blue Grass
Oct 19
LEX7:25 pmLexington Blue Grass
22h 08m
2 stops
MDW4:33 pmChicago Midway
$590
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 October 13, 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

Sat 11/8

4:23 pm-12:05 am

1 stop6h 42m

Lexington Blue Grass

Sat 11/15

6:00 am-9:53 am

1 stop4h 53m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 12/10

6:00 am-12:21 pm

1 stop5h 21m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$222

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 12/11

6:00 am-12:21 pm

1 stop5h 21m

Lexington Blue Grass

Sun 1/4

6:20 am-8:49 am

1 stop3h 29m

$234

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 12/11

6:00 am-12:21 pm

1 stop5h 21m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$247

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 12/10

5:38 pm-12:08 am

1 stop5h 30m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$271

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 12/12

1:14 pm-5:21 pm

1 stop3h 07m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$284

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/30

6:40 pm-3:20 pm

1 stop19h 40m

Lexington Blue Grass

Sun 11/2

9:41 pm-8:32 am

1 stop11h 51m

$289

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 12/13

6:46 pm-9:52 am

1 stop14h 06m

Lexington Blue Grass

Sat 1/3

6:20 am-8:49 am

1 stop3h 29m

$297

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 10/28

6:00 am-12:18 pm

1 stop5h 18m

Lexington Blue Grass

Sat 11/1

3:46 pm-10:14 pm

1 stop7h 28m

$301

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/30

6:40 pm-3:20 pm

1 stop19h 40m

Lexington Blue Grass

Sun 11/2

10:19 pm-4:52 pm

2 stops19h 33m

$340

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $259. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday 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 $304.

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 $290. 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

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.

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