Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Lexington to Chicago from $189

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 7/4. 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

Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:02 pm - 4:15 pm
LEX
-
MDW
4h 13m
1 stop
Delta Logo
10:35 am - 5:12 pm
MDW
-
LEX
5h 37m
1 stop
$269Delta
Wed, Aug 5 - Wed, Aug 12
Delta Logo
7:35 am - 12:33 pm
LEX
-
MDW
5h 58m
1 stop
Delta Logo
1:00 pm - 5:10 pm
MDW
-
LEX
3h 10m
1 stop
$282Delta
Thu, Aug 6 - Sat, Aug 15
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
$284Delta
Mon, May 18 - Sat, May 23
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
$299Delta
Fri, May 15 - Sat, May 16
Delta Logo
7:35 am - 12:41 pm
LEX
-
MDW
6h 06m
1 stop
Delta Logo
6:00 am - 12:35 pm
MDW
-
LEX
5h 35m
1 stop
$302Delta
Mon, Jun 29 - Wed, Sep 16
Allegiant Air Logo
3:05 pm - 2:59 pm
LEX
-
MDW
24h 54m
2 stops
Allegiant Air Logo
9:14 am - 8:13 am
MDW
-
LEX
21h 59m
1 stop
$311Allegiant Air
Sun, Aug 9 - Thu, Aug 13
Delta Logo
6:00 am - 12:00 pm
LEX
-
MDW
7h 00m
1 stop
Delta Logo
4:25 pm - 12:04 am
MDW
-
LEX
6h 39m
1 stop
$312Delta
Wed, Jun 10 - Sat, Jun 13
Delta Logo
3:32 pm - 9:09 pm
LEX
-
MDW
6h 37m
1 stop
Delta Logo
6:23 am - 12:19 pm
MDW
-
LEX
4h 56m
1 stop
$314Delta
Thu, May 21 - Wed, May 27
Allegiant Air Logo
3:05 pm - 2:59 pm
LEX
-
MDW
24h 54m
2 stops
Allegiant Air Logo
9:14 am - 8:13 am
MDW
-
LEX
21h 59m
1 stop
$323Allegiant Air
Sun, Aug 9 - Sun, Aug 16
Delta Logo
3:32 pm - 9:09 pm
LEX
-
MDW
6h 37m
1 stop
Delta Logo
10:59 am - 5:13 pm
MDW
-
LEX
5h 14m
1 stop
$329Delta
Sat, May 16 - Mon, May 18

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

Delta flights from Lexington to Chicago Midway Airport

Our best Delta deals on Lexington to Chicago Midway Airport flight tickets
Delta
Aug 5
LEX1:02 pmLexington Blue Grass
4h 13m
1 stop
MDW4:15 pmChicago Midway
Aug 12
MDW10:35 amChicago Midway
5h 37m
1 stop
LEX5:12 pmLexington Blue Grass
$269
Delta
Aug 6
LEX7:35 amLexington Blue Grass
5h 58m
1 stop
MDW12:33 pmChicago Midway
Aug 15
MDW1:00 pmChicago Midway
3h 10m
1 stop
LEX5:10 pmLexington Blue Grass
$282
Delta
May 18
LEX8:04 amLexington Blue Grass
5h 38m
1 stop
MDW12:42 pmChicago Midway
May 23
MDW6:23 amChicago Midway
4h 56m
1 stop
LEX12:19 pmLexington Blue Grass
$284

Allegiant Air flights from Lexington to Chicago Midway Airport

Our best Allegiant Air deals on Lexington to Chicago Midway Airport flight tickets
Allegiant Air
Aug 9
LEX3:05 pmLexington Blue Grass
24h 54m
2 stops
MDW2:59 pmChicago Midway
Aug 13
MDW9:14 amChicago Midway
21h 59m
1 stop
LEX8:13 amLexington Blue Grass
$311
Allegiant Air
Aug 9
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
$323
Allegiant Air
Aug 8
LEX5:12 pmLexington Blue Grass
21h 47m
2 stops
MDW1:59 pmChicago Midway
Aug 13
MDW9:14 amChicago Midway
21h 59m
1 stop
LEX8:13 amLexington Blue Grass
$337

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 May 2, 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

Wed 8/5

1:02 pm-4:15 pm

1 stop4h 13m

Chicago Midway

Wed 8/12

10:35 am-5:12 pm

1 stop5h 37m

$269
Quickest round-trip

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 8/6

7:35 am-12:33 pm

1 stop5h 58m

Chicago Midway

Sat 8/15

1:00 pm-5:10 pm

1 stop3h 10m

$282

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Mon 5/18

8:04 am-12:42 pm

1 stop5h 38m

Chicago Midway

Sat 5/23

6:23 am-12:19 pm

1 stop4h 56m

$284

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 5/15

8:04 am-12:42 pm

1 stop5h 38m

Chicago Midway

Sat 5/16

6:23 am-12:19 pm

1 stop4h 56m

$299

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Mon 6/29

7:35 am-12:41 pm

1 stop6h 06m

Chicago Midway

Wed 9/16

6:00 am-12:35 pm

1 stop5h 35m

$302

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sun 8/9

3:05 pm-2:59 pm

2 stops24h 54m

Chicago Midway

Thu 8/13

9:14 am-8:13 am

1 stop21h 59m

$311

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 6/10

6:00 am-12:00 pm

1 stop7h 00m

Chicago Midway

Sat 6/13

4:25 pm-12:04 am

1 stop6h 39m

$312

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 5/21

3:32 pm-9:09 pm

1 stop6h 37m

Chicago Midway

Wed 5/27

6:23 am-12:19 pm

1 stop4h 56m

$314

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sun 8/9

3:05 pm-2:59 pm

2 stops24h 54m

Chicago Midway

Sun 8/16

9:14 am-8:13 am

1 stop21h 59m

$323

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 5/16

3:32 pm-9:09 pm

1 stop6h 37m

Chicago Midway

Mon 5/18

10:59 am-5:13 pm

1 stop5h 14m

$329

Flights are sorted by cheapest round-trip flights first.

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

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 12m

Direct flights

None
The fastest flight from Lexington to Chicago Midway Airport takes 4h 12m
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 12m.

  • 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
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

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.

An easier way to manage your Chicago Midway Airport 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
Mon 6/1
Mon 6/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago