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Cheap flights from Lexington to Chicago from $158

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Lexington to Chicago departing on 7/26. 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

Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:30 pm - 10:36 pm
LEX
-
MDW
7h 06m
1 stop
Delta Logo
6:05 am - 12:11 pm
MDW
-
LEX
5h 06m
1 stop
$269Delta
Sat, Aug 22 - Wed, Aug 26
Delta Logo
7:35 am - 12:39 pm
LEX
-
MDW
6h 04m
1 stop
Delta Logo
5:10 pm - 11:59 pm
MDW
-
LEX
5h 49m
1 stop
$284Delta
Fri, Aug 14 - Mon, Aug 17
Delta Logo
7:35 am - 12:46 pm
LEX
-
MDW
6h 11m
1 stop
Delta Logo
6:00 am - 12:17 pm
MDW
-
LEX
5h 17m
1 stop
$299Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
7:35 am - 12:34 pm
LEX
-
MDW
5h 59m
1 stop
Delta Logo
10:35 am - 5:10 pm
MDW
-
LEX
5h 35m
1 stop
$314Delta
Sat, Oct 3 - Tue, Oct 6
Delta Logo
10:53 am - 3:25 pm
LEX
-
MDW
5h 32m
1 stop
Delta Logo
4:30 pm - 10:42 pm
MDW
-
LEX
5h 12m
1 stop
$329Delta
Thu, Sep 10 - Sat, Sep 12
Delta Logo
5:56 pm - 10:36 pm
LEX
-
MDW
5h 40m
1 stop
Delta Logo
6:05 am - 12:11 pm
MDW
-
LEX
5h 06m
1 stop
$344Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
8:00 am - 12:38 pm
LEX
-
MDW
5h 38m
1 stop
Delta Logo
6:00 am - 12:17 pm
MDW
-
LEX
5h 17m
1 stop
$354Delta
Sat, Jul 25 - Mon, Jul 27
Delta Logo
5:56 pm - 10:15 pm
LEX
-
MDW
5h 19m
1 stop
Delta Logo
12:41 pm - 7:14 pm
MDW
-
LEX
5h 33m
1 stop
$404Delta
Sat, Jul 11 - Mon, Jul 13
Delta Logo
5:56 pm - 10:17 pm
LEX
-
MDW
5h 21m
1 stop
Delta Logo
4:25 pm - 12:04 am
MDW
-
LEX
6h 39m
1 stop
$409Delta
Wed, Jul 1 - Sat, Jul 4
Delta Logo
5:56 pm - 10:15 pm
LEX
-
MDW
5h 19m
1 stop
Delta Logo
12:41 pm - 7:14 pm
MDW
-
LEX
5h 33m
1 stop
$419Delta
Thu, Jul 9 - Mon, Jul 13

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Delta flights from Lexington to Chicago Midway Airport

Our best Delta deals on Lexington to Chicago Midway Airport flight tickets
Delta
Aug 22
LEX4:30 pmLexington Blue Grass
7h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 26
MDW6:05 amChicago Midway
5h 06m
1 stop
LEX12:11 pmLexington Blue Grass
$269
Delta
Aug 14
LEX7:35 amLexington Blue Grass
6h 04m
1 stop
MDW12:39 pmChicago Midway
Aug 17
MDW5:10 pmChicago Midway
5h 49m
1 stop
LEX11:59 pmLexington Blue Grass
$284
Delta
Jul 3
LEX7:35 amLexington Blue Grass
6h 11m
1 stop
MDW12:46 pmChicago Midway
Jul 8
MDW6:00 amChicago Midway
5h 17m
1 stop
LEX12:17 pmLexington Blue Grass
$299

Allegiant Air flights from Lexington to Chicago Midway Airport

Our best Allegiant Air deals on Lexington to Chicago Midway Airport flight tickets
Allegiant Air
Jul 8
LEX5:58 pmLexington Blue Grass
15h 20m
1 stop
MDW8:18 amChicago Midway
Jul 12
MDW2:48 pmChicago Midway
24h 23m
2 stops
LEX4:11 pmLexington Blue Grass
$633
Allegiant Air
Jun 27
LEX8:58 amLexington Blue Grass
24h 23m
1 stop
MDW8:21 amChicago Midway
Jun 28
MDW2:46 pmChicago Midway
24h 59m
2 stops
LEX4:45 pmLexington Blue Grass
$767

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 June 21, 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 8/22

4:30 pm-10:36 pm

1 stop7h 06m

Chicago Midway

Wed 8/26

6:05 am-12:11 pm

1 stop5h 06m

$269

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 8/14

7:35 am-12:39 pm

1 stop6h 04m

Chicago Midway

Mon 8/17

5:10 pm-11:59 pm

1 stop5h 49m

$284

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 7/3

7:35 am-12:46 pm

1 stop6h 11m

Chicago Midway

Wed 7/8

6:00 am-12:17 pm

1 stop5h 17m

$299

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 10/3

7:35 am-12:34 pm

1 stop5h 59m

Chicago Midway

Tue 10/6

10:35 am-5:10 pm

1 stop5h 35m

$314
Quickest round-trip

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 9/10

10:53 am-3:25 pm

1 stop5h 32m

Chicago Midway

Sat 9/12

4:30 pm-10:42 pm

1 stop5h 12m

$329

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 8/27

5:56 pm-10:36 pm

1 stop5h 40m

Chicago Midway

Sun 8/30

6:05 am-12:11 pm

1 stop5h 06m

$344

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 7/25

8:00 am-12:38 pm

1 stop5h 38m

Chicago Midway

Mon 7/27

6:00 am-12:17 pm

1 stop5h 17m

$354

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 7/11

5:56 pm-10:15 pm

1 stop5h 19m

Chicago Midway

Mon 7/13

12:41 pm-7:14 pm

1 stop5h 33m

$404

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 7/1

5:56 pm-10:17 pm

1 stop5h 21m

Chicago Midway

Sat 7/4

4:25 pm-12:04 am

1 stop6h 39m

$409

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 7/9

5:56 pm-10:15 pm

1 stop5h 19m

Chicago Midway

Mon 7/13

12:41 pm-7:14 pm

1 stop5h 33m

$419

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?

Allegiant Air and Delta are the most popular carriers 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 52m

Direct flights

None
The fastest flight from Lexington to Chicago Midway Airport takes 4h 52m
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

Frequently asked questions about flying from Lexington to Chicago Midway Airport

  • 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 52m.

  • 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?

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Munster
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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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