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Cheap flights from Chicago to Lexington from $135

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Lexington

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:15 am - 10:50 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 35mnonstop
American Airlines Logo
5:15 am - 5:59 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 44mnonstop
$316American Airlines
Thu, Nov 26 - Mon, Nov 30
American Airlines Logo
4:20 pm - 6:56 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 36mnonstop
American Airlines Logo
11:17 am - 12:00 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 43mnonstop
$319American Airlines
Thu, Dec 24 - Mon, Jan 4
United Airlines Logo
2:40 pm - 5:22 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 42mnonstop
United Airlines Logo
6:05 pm - 7:00 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 55mnonstop
$319United Airlines
Fri, Feb 5 - Sun, Feb 7
United Airlines Logo
5:55 pm - 8:37 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 42mnonstop
United Airlines Logo
8:45 am - 9:32 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 47mnonstop
$319United Airlines
Mon, Nov 30 - Mon, Dec 7
United Airlines Logo
2:50 pm - 5:30 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 40mnonstop
United Airlines Logo
5:25 am - 6:10 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 45mnonstop
$319United Airlines
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
8:28 am - 11:05 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 37mnonstop
American Airlines Logo
3:55 pm - 4:44 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 49mnonstop
$319American Airlines
Tue, Mar 23 - Sun, Mar 28
American Airlines Logo
9:15 pm - 11:42 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 27mnonstop
American Airlines Logo
5:15 am - 5:59 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 44mnonstop
$319American Airlines
Wed, Nov 25 - Mon, Nov 30
Delta Logo
4:13 pm - 10:49 pmMDW  Chicago Midway-LEX Lexington Blue Grass
5h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:50 pm - 4:18 pmLEX  Lexington Blue Grass-MDW Chicago Midway
4h 28m1 stop Atlanta Hartsfield-Jackson
$339Delta
Thu, Nov 26 - Mon, Nov 30
Delta Logo
6:00 am - 11:49 amMDW  Chicago Midway-LEX Lexington Blue Grass
4h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:35 am - 11:25 amLEX  Lexington Blue Grass-MDW Chicago Midway
4h 50m1 stop Detroit Metropolitan Wayne County
$339Delta
Mon, Nov 23 - Fri, Nov 27
Delta Logo
6:00 am - 11:49 amMDW  Chicago Midway-LEX Lexington Blue Grass
4h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:59 amLEX  Lexington Blue Grass-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
$339Delta
Thu, Nov 19 - Sun, Nov 22

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American Airlines flights from Chicago to Lexington

Our best American Airlines deals on Chicago to Lexington flight tickets
American Airlines
Nov 26
ORD8:15 amChicago O'Hare Intl
1h 35m
LEX10:50 amLexington Blue Grass
Nov 30
LEX5:15 amLexington Blue Grass
1h 44m
ORD5:59 amChicago O'Hare Intl
$316
American Airlines
Nov 26
ORD2:30 pmChicago O'Hare Intl
1h 39m
LEX5:09 pmLexington Blue Grass
Nov 29
LEX11:20 amLexington Blue Grass
1h 51m
ORD12:11 pmChicago O'Hare Intl
$321
American Airlines
Nov 26
ORD5:19 amChicago O'Hare Intl
6h 41m
1 stop
LEX1:00 pmLexington Blue Grass
Nov 30
LEX5:15 amLexington Blue Grass
1h 44m
ORD5:59 amChicago O'Hare Intl
$326

Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets
Delta
Nov 19
MDW6:00 amChicago Midway
4h 49m
1 stop
LEX11:49 amLexington Blue Grass
Nov 22
LEX6:00 amLexington Blue Grass
6h 59m
1 stop
MDW11:59 amChicago Midway
$339
Delta
Nov 19
ORD9:51 amChicago O'Hare Intl
4h 02m
1 stop
LEX2:53 pmLexington Blue Grass
Nov 21
LEX3:38 pmLexington Blue Grass
6h 11m
1 stop
ORD8:49 pmChicago O'Hare Intl
$354
Delta
Nov 17
ORD11:19 amChicago O'Hare Intl
4h 50m
1 stop
LEX5:09 pmLexington Blue Grass
Nov 21
LEX5:49 pmLexington Blue Grass
3h 28m
1 stop
ORD8:17 pmChicago O'Hare Intl
$369

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Thu 11/26

8:15 am-10:50 am

Nonstop1h 35m

Lexington Blue Grass

Mon 11/30

5:15 am-5:59 am

Nonstop1h 44m

$316

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Thu 12/24

4:20 pm-6:56 pm

Nonstop1h 36m

Lexington Blue Grass

Mon 1/4

11:17 am-12:00 pm

Nonstop1h 43m

$319

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Fri 2/5

2:40 pm-5:22 pm

Nonstop1h 42m

Lexington Blue Grass

Sun 2/7

6:05 pm-7:00 pm

Nonstop1h 55m

$319

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Mon 11/30

5:55 pm-8:37 pm

Nonstop1h 42m

Lexington Blue Grass

Mon 12/7

8:45 am-9:32 am

Nonstop1h 47m

$319

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Wed 11/25

2:50 pm-5:30 pm

Nonstop1h 40m

Lexington Blue Grass

Mon 11/30

5:25 am-6:10 am

Nonstop1h 45m

$319

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Tue 3/23

8:28 am-11:05 am

Nonstop1h 37m

Lexington Blue Grass

Sun 3/28

3:55 pm-4:44 pm

Nonstop1h 49m

$319
Quickest round-trip

ChicagoLexington

ORD Chicago O'Hare Intl - LEX Lexington Blue Grass

ORDLEX

Chicago O'Hare Intl

Wed 11/25

9:15 pm-11:42 pm

Nonstop1h 27m

Lexington Blue Grass

Mon 11/30

5:15 am-5:59 am

Nonstop1h 44m

$319

ChicagoLexington

MDW Chicago Midway - LEX Lexington Blue Grass

MDWLEX

Chicago Midway

Thu 11/26

4:13 pm-10:49 pm

1 stop5h 36m

Lexington Blue Grass

Mon 11/30

12:50 pm-4:18 pm

1 stop4h 28m

$339

ChicagoLexington

MDW Chicago Midway - LEX Lexington Blue Grass

MDWLEX

Chicago Midway

Mon 11/23

6:00 am-11:49 am

1 stop4h 49m

Lexington Blue Grass

Fri 11/27

7:35 am-11:25 am

1 stop4h 50m

$339

ChicagoLexington

MDW Chicago Midway - LEX Lexington Blue Grass

MDWLEX

Chicago Midway

Thu 11/19

6:00 am-11:49 am

1 stop4h 49m

Lexington Blue Grass

Sun 11/22

6:00 am-11:59 am

1 stop6h 59m

$339

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 Lexington from

How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Lexington?

Prices are currently typical for flights on this route.

Typical prices usually range from $279 to $400.
The lowest price recently found on this route was $316.

What is the cheapest month to fly to Lexington?

In general, December is the cheapest month to fly from Chicago to Lexington. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $217. If you are unable to visit Lexington during the month of December, then departing from Chicago during the month November is also very affordable. Most momondo users find prices during this month for around $303.

What is the cheapest day to depart on your flight to Lexington?

On average, the least expensive day to fly to Lexington from Chicago is on a Saturday. momondo users have found tickets for Saturday departures for as low as $269. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $497.

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 morning when flights can be purchased for as low as $345. Try not to purchase tickets in the afternoon because they tend to be around $453. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Lexington Blue Grass flight route?

Fly from Chicago O'Hare Intl to Lexington Blue Grass for the best Chicago - Lexington Blue Grass flight prices

What cabin class options are available on Chicago to Lexington flights?

There are 4 cabin classes available to choose from on Chicago to Lexington flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Lexington flights?

No. A direct flight is the cheapest option for a flight between Chicago to Lexington.

How have Chicago to Lexington flight prices changed over time?

As of November 2026, prices for Chicago to Lexington flights are approximately 103% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Lexington

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

Cheap Chicago to Lexington (CHI to LEX) flight deals and tips

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

Best Price Found

$135

Fastest flight time

1h 22m

Direct flights

Every day

Airports in Lexington

1 airport
The best one-way flight to Lexington from Chicago in the past 72 hours is $135. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $316.
The fastest flight from Chicago to Lexington takes 1h 22m
Direct flights go from Chicago to Lexington every day.
There is 1 airport in Lexington. From Chicago there are direct flights to Lexington Blue Grass (LEX).
Search flight deals

Frequently asked questions about flying from Chicago to Lexington

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

    Lexington Blue Grass is 312.4 mi away from Chicago. In terms of flight time, this usually takes a little over 1h 22m.

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

    Prices for flights from Chicago to Lexington Blue Grass Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Lexington Blue Grass Airport?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Lexington Blue Grass Airport.

  • What documentation or ID do you need to fly to Lexington Blue Grass Airport?

    The travel and health documents you'll need for your trip to Lexington Blue Grass Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Lexington Blue Grass Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Lexington?

  • What is the most popular airline from Chicago to Lexington?

Best airlines flying from Chicago to Lexington

Compare and see reviews for airlines that fly from Chicago to Lexington with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $189Free CancellationRating
7.3
10,460 reviews
Search United Airlines flights
American AirlinesPriceFrom $204Free CancellationRating
7.0
12,230 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Lexington

    United Airlines operates around 39 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $430, but momondo users have found United Airlines deals from Chicago to Lexington from as low as $189 round-trip. United Airlines has been scored 7.3/10 in 10,459 reviews.

  • American Airlines Flights From Chicago to Lexington

    American Airlines (7.0/10 from 12,230 reviews) operates around 11 flights from Chicago to Lexington in any given week. The average American Airlines airfare for this route is around $340, with deals from around $204 rare but found on momondo. Referenced prices are for round-trip Chicago to Lexington flight searches in the last 72 hours.

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Richmond
Georgetown
Somerset
Winchester
Frankfort
Danville
Berea
Versailles
Carlisle

Why use momondo?

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

Finding the right flight to Lexington from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Lexington quick and easy, saving you time and money.

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

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

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

Once all potential Chicago to Lexington flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Chicago to Lexington now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Lexington and let you know when they change.

An easier way to manage your Lexington trip

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