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Cheap flights from Lexington to Chicago 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 Lexington to Chicago departing on 10/20. 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
6:00 am - 9:59 amLEX  Lexington Blue Grass-MDW Chicago Midway
4h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:11 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 06m1 stop Atlanta Hartsfield-Jackson
$279Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
6:00 am - 10:33 amLEX  Lexington Blue Grass-MDW Chicago Midway
5h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:52 amMDW  Chicago Midway-LEX Lexington Blue Grass
4h 52m1 stop Atlanta Hartsfield-Jackson
$279Delta
Tue, Nov 17 - Sun, Nov 22
Delta Logo
6:00 am - 9:52 amLEX  Lexington Blue Grass-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:25 pm - 11:56 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 31m1 stop Atlanta Hartsfield-Jackson
$279Delta
Fri, Jan 29 - Sun, Jan 31
Delta Logo
5:00 pm - 10:36 pmLEX  Lexington Blue Grass-MDW Chicago Midway
6h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:11 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 06m1 stop Atlanta Hartsfield-Jackson
$279Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
7:30 am - 12:33 pmLEX  Lexington Blue Grass-MDW Chicago Midway
6h 03m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:00 pm - 5:09 pmMDW  Chicago Midway-LEX Lexington Blue Grass
3h 09m1 stop Detroit Metropolitan Wayne County
$279Delta
Fri, Jan 8 - Sun, Jan 10
Delta Logo
10:28 am - 12:47 pmLEX  Lexington Blue Grass-MDW Chicago Midway
3h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
11:28 am - 7:05 pmMDW  Chicago Midway-LEX Lexington Blue Grass
6h 37m1 stop Atlanta Hartsfield-Jackson
$279Delta
Fri, Nov 6 - Tue, Nov 10
Delta Logo
5:55 pm - 10:10 pmLEX  Lexington Blue Grass-MDW Chicago Midway
5h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:35 am - 5:10 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 35m1 stop Atlanta Hartsfield-Jackson
$279Delta
Sat, Jan 16 - Sun, Jan 17
Delta Logo
5:59 pm - 10:56 pmLEX  Lexington Blue Grass-MDW Chicago Midway
5h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:52 amMDW  Chicago Midway-LEX Lexington Blue Grass
4h 52m1 stop Atlanta Hartsfield-Jackson
$279Delta
Thu, Dec 3 - Sun, Dec 6
Delta Logo
4:30 pm - 10:44 pmLEX  Lexington Blue Grass-MDW Chicago Midway
7h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:11 pm - 11:59 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 48m1 stop Atlanta Hartsfield-Jackson
$279Delta
Tue, Sep 8 - Tue, Sep 15
Delta Logo
5:00 pm - 10:36 pmLEX  Lexington Blue Grass-MDW Chicago Midway
6h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:44 amMDW  Chicago Midway-LEX Lexington Blue Grass
4h 39m1 stop Atlanta Hartsfield-Jackson
$294Delta
Sat, Sep 5 - Tue, Sep 8

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Allegiant Air flights from Lexington to Chicago Midway Airport

Our best Allegiant Air deals on Lexington to Chicago Midway Airport flight tickets
Allegiant Air
Oct 18
LEX2:37 pmLexington Blue Grass
22h 59m
2 stops
MDW12:36 pmChicago Midway
Oct 22
MDW10:08 amChicago Midway
27h 39m
1 stop
LEX2:47 pmLexington Blue Grass
$444
Allegiant Air
Aug 13
LEX3:05 pmLexington Blue Grass
24h 54m
2 stops
MDW2:59 pmChicago Midway
Aug 16
MDW9:14 amChicago Midway
21h 59m
1 stop
LEX8:13 amLexington Blue Grass
$603

Delta flights from Lexington to Chicago Midway Airport

Our best Delta deals on Lexington to Chicago Midway Airport flight tickets
Delta
Sep 1
LEX5:00 pmLexington Blue Grass
6h 36m
1 stop
MDW10:36 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
5h 06m
1 stop
LEX12:11 pmLexington Blue Grass
$279
Delta
Sep 1
LEX6:00 amLexington Blue Grass
4h 59m
1 stop
MDW9:59 amChicago Midway
Sep 6
MDW6:05 amChicago Midway
5h 06m
1 stop
LEX12:11 pmLexington Blue Grass
$294
Delta
Aug 22
LEX7:35 amLexington Blue Grass
6h 04m
1 stop
MDW12:39 pmChicago Midway
Aug 26
MDW10:54 amChicago Midway
5h 17m
1 stop
LEX5:11 pmLexington Blue Grass
$309

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 August 12, 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 Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Wed 9/2

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Sat 9/5

6:05 am-12:11 pm

1 stop5h 06m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Tue 11/17

6:00 am-10:33 am

1 stop5h 33m

Chicago Midway

Sun 11/22

6:00 am-11:52 am

1 stop4h 52m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Fri 1/29

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Sun 1/31

5:25 pm-11:56 pm

1 stop5h 31m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Tue 9/1

5:00 pm-10:36 pm

1 stop6h 36m

Chicago Midway

Sat 9/5

6:05 am-12:11 pm

1 stop5h 06m

$279
Quickest round-trip

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Fri 1/8

7:30 am-12:33 pm

1 stop6h 03m

Chicago Midway

Sun 1/10

1:00 pm-5:09 pm

1 stop3h 09m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Fri 11/6

10:28 am-12:47 pm

1 stop3h 19m

Chicago Midway

Tue 11/10

11:28 am-7:05 pm

1 stop6h 37m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Sat 1/16

5:55 pm-10:10 pm

1 stop5h 15m

Chicago Midway

Sun 1/17

10:35 am-5:10 pm

1 stop5h 35m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Thu 12/3

5:59 pm-10:56 pm

1 stop5h 57m

Chicago Midway

Sun 12/6

6:00 am-11:52 am

1 stop4h 52m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Tue 9/8

4:30 pm-10:44 pm

1 stop7h 14m

Chicago Midway

Tue 9/15

5:11 pm-11:59 pm

1 stop5h 48m

$279

LexingtonChicago

LEX Lexington Blue Grass - MDW Chicago Midway

LEXMDW

Lexington Blue Grass

Sat 9/5

5:00 pm-10:36 pm

1 stop6h 36m

Chicago Midway

Tue 9/8

6:05 am-11:44 am

1 stop4h 39m

$294

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 59m

Direct flights

None
The fastest flight from Lexington to Chicago Midway Airport takes 4h 59m
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 59m.

  • 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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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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