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Cheap flights from Lexington to Chicago from $229

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Lexington to Chicago departing on 4/25. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:40 am - 12:43 pm
LEX
-
MDW
6h 03m
1 stop
Delta Logo
6:00 am - 11:41 am
MDW
-
LEX
4h 41m
1 stop
$229Delta
Sat, Apr 25 - Wed, Apr 29
Delta Logo
7:40 am - 12:43 pm
LEX
-
MDW
6h 03m
1 stop
Delta Logo
6:00 am - 1:38 pm
MDW
-
LEX
6h 38m
1 stop
$249Delta
Thu, Apr 23 - Sat, Apr 25
Delta Logo
12:46 pm - 4:26 pm
LEX
-
MDW
4h 40m
1 stop
Delta Logo
5:40 am - 11:46 am
MDW
-
LEX
5h 06m
1 stop
$269Delta
Wed, Apr 29 - Sat, May 2
Multiple Airlines Logo
9:45 pm - 10:14 pm
LEX
-
MDW
25h 29m
2 stops
Multiple Airlines Logo
9:14 am - 8:55 pm
MDW
-
LEX
10h 41m
1 stop
$305Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Delta Logo
7:40 am - 12:43 pm
LEX
-
MDW
6h 03m
1 stop
Delta Logo
6:00 am - 1:38 pm
MDW
-
LEX
6h 38m
1 stop
$309Delta
Thu, Apr 23 - Sat, Apr 25
Delta Logo
8:04 am - 12:42 pm
LEX
-
MDW
5h 38m
1 stop
Delta Logo
6:23 am - 12:19 pm
MDW
-
LEX
4h 56m
1 stop
$314Delta
Thu, May 7 - Sun, May 10
Delta Logo
8:04 am - 12:42 pm
LEX
-
MDW
5h 38m
1 stop
Delta Logo
6:23 am - 12:19 pm
MDW
-
LEX
4h 56m
1 stop
$324Delta
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
9:51 am - 10:19 pm
LEX
-
MDW
13h 28m
2 stops
Multiple Airlines Logo
9:16 am - 8:42 am
MDW
-
LEX
22h 26m
1 stop
$327Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
9:31 am - 7:31 pm
LEX
-
MDW
11h 00m
2 stops
Multiple Airlines Logo
9:16 am - 8:42 am
MDW
-
LEX
22h 26m
1 stop
$350Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Delta Logo
3:31 pm - 9:09 pm
LEX
-
MDW
6h 38m
1 stop
Delta Logo
5:10 pm - 11:58 pm
MDW
-
LEX
5h 48m
1 stop
$354Delta
Sat, May 16 - Mon, May 18

Delta flights from Lexington to Chicago Midway Airport

Our best Delta deals on Lexington to Chicago Midway Airport flight tickets
Delta
Apr 25
LEX7:40 amLexington Blue Grass
6h 03m
1 stop
MDW12:43 pmChicago Midway
Apr 29
MDW6:00 amChicago Midway
4h 41m
1 stop
LEX11:41 amLexington Blue Grass
$229
Delta
Apr 23
LEX7:40 amLexington Blue Grass
6h 03m
1 stop
MDW12:43 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
6h 38m
1 stop
LEX1:38 pmLexington Blue Grass
$249
Delta
Apr 29
LEX12:46 pmLexington Blue Grass
4h 40m
1 stop
MDW4:26 pmChicago Midway
May 2
MDW5:40 amChicago Midway
5h 06m
1 stop
LEX11:46 amLexington Blue Grass
$269

momondo Fare Finder

 
Customize your flight search to find flights from Lexington to Chicago Midway Airport 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 March 14, 2026.
Use the filters below to find and compare flights from Lexington to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 4/25

7:40 am-12:43 pm

1 stop6h 03m

Chicago Midway

Wed 4/29

6:00 am-11:41 am

1 stop4h 41m

$229

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/23

7:40 am-12:43 pm

1 stop6h 03m

Chicago Midway

Sat 4/25

6:00 am-1:38 pm

1 stop6h 38m

$249
Quickest round-trip

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/29

12:46 pm-4:26 pm

1 stop4h 40m

Chicago Midway

Sat 5/2

5:40 am-11:46 am

1 stop5h 06m

$269

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 4/24

9:45 pm-10:14 pm

2 stops25h 29m

Chicago Midway

Mon 4/27

9:14 am-8:55 pm

1 stop10h 41m

$305

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/23

7:40 am-12:43 pm

1 stop6h 03m

Chicago Midway

Sat 4/25

6:00 am-1:38 pm

1 stop6h 38m

$309

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 5/7

8:04 am-12:42 pm

1 stop5h 38m

Chicago Midway

Sun 5/10

6:23 am-12:19 pm

1 stop4h 56m

$314

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 5/7

8:04 am-12:42 pm

1 stop5h 38m

Chicago Midway

Sun 5/10

6:23 am-12:19 pm

1 stop4h 56m

$324

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 5/7

9:51 am-10:19 pm

2 stops13h 28m

Chicago Midway

Sun 5/10

9:16 am-8:42 am

1 stop22h 26m

$327

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/23

9:31 am-7:31 pm

2 stops11h 00m

Chicago Midway

Sun 4/26

9:16 am-8:42 am

1 stop22h 26m

$350

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 5/16

3:31 pm-9:09 pm

1 stop6h 38m

Chicago Midway

Mon 5/18

5:10 pm-11:58 pm

1 stop5h 48m

$354

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 airline that flies from Lexington Blue Grass to Chicago Midway?

Delta is the most popular carrier operating from Lexington Blue Grass to Chicago Midway

When to book flights from Lexington to Chicago Midway Airport

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

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

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

Fastest flight time

4h 50m

Direct flights

None
The fastest flight from Lexington to Chicago Midway Airport takes 4h 50m
There are no direct flights from Lexington to Chicago Midway Airport. There are no popular flight routes from Lexington to Chicago Midway Airport.
Search flight deals

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

    Chicago Midway is 310.7 mi away from Lexington Blue Grass. In terms of flight time, this usually takes a little over 4h 50m.

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

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

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Lexington to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Lexington to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Lexington and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Lexington to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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