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Cheap flights from Chicago to Lexington from $111

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Lexington departing on 11/13. 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

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Cheap round-trip flights

United Airlines Logo
6:15 pm - 9:01 pmORD-LEX
1h 46mnonstop
United Airlines Logo
7:33 pm - 8:25 pmLEX-ORD
1h 52mnonstop
$189United Airlines
Find Deal
vie., oct. 10 - dom., oct. 12
United Airlines Logo
6:15 pm - 9:01 pmORD-LEX
1h 46mnonstop
United Airlines Logo
7:33 pm - 8:25 pmLEX-ORD
1h 52mnonstop
$194United Airlines
Find Deal
vie., oct. 10 - dom., oct. 12
American Airlines Logo
8:44 pm - 5:29 pmORD-LEX
19h 45m1 stop
American Airlines Logo
7:19 pm - 8:02 pmLEX-ORD
1h 43mnonstop
$203American Airlines
Find Deal
mié., oct. 22 - jue., oct. 23
American Airlines Logo
8:44 pm - 5:29 pmORD-LEX
19h 45m1 stop
American Airlines Logo
7:19 pm - 8:02 pmLEX-ORD
1h 43mnonstop
$208American Airlines
Find Deal
mié., oct. 22 - jue., oct. 23
Multiple Airlines Logo
5:17 pm - 2:42 pmORD-LEX
20h 25m1 stop
Multiple Airlines Logo
7:25 pm - 5:39 pmLEX-ORD
23h 14m1 stop
$267Multiple Airlines
Find Deal
mar., sep. 30 - jue., oct. 2
Delta Logo
4:23 pm - 12:05 amMDW-LEX
6h 42m1 stop
Delta Logo
7:30 am - 12:34 pmLEX-MDW
6h 04m1 stop
$271Delta
Find Deal
vie., oct. 31 - mié., nov. 26
Delta Logo
6:00 am - 12:15 pmMDW-LEX
5h 15m1 stop
Delta Logo
10:24 am - 12:28 pmLEX-MDW
3h 04m1 stop
$276Delta
Find Deal
mar., sep. 30 - sáb., oct. 4
Multiple Airlines Logo
5:05 am - 6:35 pmORD-LEX
12h 30m1 stop
Multiple Airlines Logo
7:25 pm - 10:50 amLEX-ORD
16h 25m1 stop
$282Multiple Airlines
Find Deal
dom., oct. 19 - jue., oct. 23
Allegiant Air Logo
5:40 pm - 8:17 amMDW-LEX
13h 37m1 stop
Allegiant Air Logo
7:25 pm - 4:33 pmLEX-MDW
22h 08m2 stops
$354Allegiant Air
Find Deal
jue., oct. 16 - dom., oct. 19
Allegiant Air Logo
5:24 pm - 7:58 amMDW-LEX
13h 34m2 stops
Allegiant Air Logo
7:25 pm - 4:33 pmLEX-MDW
22h 08m2 stops
$368Allegiant Air
Find Deal
vie., oct. 17 - dom., oct. 19

American Airlines flights from Chicago to Lexington

Our best American Airlines deals on Chicago to Lexington flight tickets
American Airlines
Oct 22
ORD8:44 pmChicago O'Hare Intl
19h 45m
1 stop
LEX5:29 pmLexington Blue Grass
Oct 23
LEX7:19 pmLexington Blue Grass
1h 43m
ORD8:02 pmChicago O'Hare Intl
$203
Find similar
American Airlines
Oct 22
ORD8:44 pmChicago O'Hare Intl
19h 45m
1 stop
LEX5:29 pmLexington Blue Grass
Oct 23
LEX7:19 pmLexington Blue Grass
1h 43m
ORD8:02 pmChicago O'Hare Intl
$208
Find similar
American Airlines
Oct 7
ORD8:44 pmChicago O'Hare Intl
19h 07m
1 stop
LEX4:51 pmLexington Blue Grass
Oct 8
LEX7:19 pmLexington Blue Grass
1h 43m
ORD8:02 pmChicago O'Hare Intl
$218
Find similar

United Airlines flights from Chicago to Lexington

Our best United Airlines deals on Chicago to Lexington flight tickets
United Airlines
Oct 10
ORD6:15 pmChicago O'Hare Intl
1h 46m
LEX9:01 pmLexington Blue Grass
Oct 12
LEX7:33 pmLexington Blue Grass
1h 52m
ORD8:25 pmChicago O'Hare Intl
$189
Find similar
United Airlines
Oct 10
ORD6:15 pmChicago O'Hare Intl
1h 46m
LEX9:01 pmLexington Blue Grass
Oct 12
LEX7:33 pmLexington Blue Grass
1h 52m
ORD8:25 pmChicago O'Hare Intl
$194
Find similar
United Airlines
Sep 30
ORD2:47 pmChicago O'Hare Intl
1h 33m
LEX5:20 pmLexington Blue Grass
Oct 4
LEX7:33 pmLexington Blue Grass
1h 52m
ORD8:25 pmChicago O'Hare Intl
$199
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Lexington 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 septiembre 17, 2025.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

vie. 10/10

6:15 pm-9:01 pm

Nonstop1h 46m

Lexington Blue Grass

dom. 10/12

7:33 pm-8:25 pm

Nonstop1h 52m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

vie. 10/10

6:15 pm-9:01 pm

Nonstop1h 46m

Lexington Blue Grass

dom. 10/12

7:33 pm-8:25 pm

Nonstop1h 52m

$194

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

mié. 10/22

8:44 pm-5:29 pm

1 stop19h 45m

Lexington Blue Grass

jue. 10/23

7:19 pm-8:02 pm

Nonstop1h 43m

$203

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

mié. 10/22

8:44 pm-5:29 pm

1 stop19h 45m

Lexington Blue Grass

jue. 10/23

7:19 pm-8:02 pm

Nonstop1h 43m

$208

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

mar. 9/30

5:17 pm-2:42 pm

1 stop20h 25m

Lexington Blue Grass

jue. 10/2

7:25 pm-5:39 pm

1 stop23h 14m

$267

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

vie. 10/31

4:23 pm-12:05 am

1 stop6h 42m

Lexington Blue Grass

mié. 11/26

7:30 am-12:34 pm

1 stop6h 04m

$271

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

mar. 9/30

6:00 am-12:15 pm

1 stop5h 15m

Lexington Blue Grass

sáb. 10/4

10:24 am-12:28 pm

1 stop3h 04m

$276

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

dom. 10/19

5:05 am-6:35 pm

1 stop12h 30m

Lexington Blue Grass

jue. 10/23

7:25 pm-10:50 am

1 stop16h 25m

$282

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

jue. 10/16

5:40 pm-8:17 am

1 stop13h 37m

Lexington Blue Grass

dom. 10/19

7:25 pm-4:33 pm

2 stops22h 08m

$354

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

vie. 10/17

5:24 pm-7:58 am

2 stops13h 34m

Lexington Blue Grass

dom. 10/19

7:25 pm-4:33 pm

2 stops22h 08m

$368

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?

What is the cheapest month to fly to Lexington?

In general, January 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 $218. If you are unable to visit Lexington during the month of January, then departing from Chicago during the month December is also very affordable. Most momondo users find prices during this month for around $237.

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $259. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday 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 $317.

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 afternoon when flights can be purchased for as low as $253. Try not to purchase tickets at noon because they tend to be around $288. 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 Blue Grass flights?

There are 4 cabin classes available to choose from on Chicago to Lexington Blue Grass 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 September 2025, prices for Chicago to Lexington flights are approximately 20% 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

$218

Fastest flight time

1h 18m

Direct flights

Every day

Airports in Lexington

1 airport
The best one-way flight to Lexington from Chicago in the past 72 hours is $218. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $224.
The fastest flight from Chicago to Lexington takes 1h 18m
Direct flights go from Chicago to Lexington every day.
There is 1 airport near Lexington: Lexington Blue Grass (LEX)
Search flight deals

  • 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 25m.

  • 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
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Lexington

    United Airlines operates around 27 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $359, but momondo users have found United Airlines deals from Chicago to Lexington from as low as $189 round-trip. United Airlines has been scored 7.4/10 in 8,926 reviews.

  • American Airlines Flights From Chicago to Lexington

    American Airlines (7.2/10 from 10,000 reviews) operates around 20 flights from Chicago to Lexington in any given week. The average American Airlines airfare for this route is around $269, with deals from around $189 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
Somerset
Georgetown
Danville
Frankfort
Winchester
Berea
Carlisle
Versailles

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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vie. 10/17
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