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Lexington

$109+ Cheap flights from Chicago (CHI) to Lexington (LEX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Chicago to Lexington

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Lexington (LEX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$189
(American Airlines)

One-way from

$109
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$284

Good round-trip deal

$224 or less

Good one-way deal

$218 or less
From Chicago (CHI) to Lexington Blue Grass
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One-way flight from Chicago (CHI) to Lexington Blue Grass
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Lexington Blue Grass.
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Price to beat on a one-way flight from Chicago (CHI) to Lexington Blue Grass.
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Find flight deals from Chicago to Lexington

Cheapest flights from Chicago to Lexington
Explore the most affordable flight options available from Chicago to Lexington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:45 pmORD - LEX
Nonstop1h 36mAmerican Airlines
Mon 10/137:19 pmLEX - ORD
Nonstop1h 43mAmerican Airlines
Deal found 9/13$189
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:45 pmORD - LEX
Nonstop1h 36mAmerican Airlines
Wed 11/56:40 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Deal found 9/14$191
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:15 pmORD - LEX
Nonstop1h 46mUnited Airlines
Sun 10/127:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Deal found 9/13$193
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/302:47 pmORD - LEX
Nonstop1h 33mUnited Airlines
Sat 10/47:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Deal found 9/14$199
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:15 pmORD - LEX
Nonstop1h 46mUnited Airlines
Sun 10/127:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Deal found 9/14$210
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/309:50 amORD - LEX
1 stop4h 07mDelta
Sat 10/45:48 pmLEX - ORD
1 stop4h 46mDelta
Deal found 9/14$219
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:10 amORD - LEX
Nonstop1h 29mAmerican Airlines
Sat 10/117:19 pmLEX - ORD
Nonstop1h 43mAmerican Airlines
Deal found 9/15$221
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:35 pmORD - LEX
1 stop19h 31mAmerican Airlines
Thu 11/66:58 pmLEX - ORD
Nonstop1h 51mAmerican Airlines
Deal found 9/15$222
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:51 amORD - LEX
Nonstop1h 33mUnited Airlines
Sat 9/276:01 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Deal found 9/13$224
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:45 pmORD - LEX
Nonstop1h 36mAmerican Airlines
Mon 10/208:02 pmLEX - ORD
1 stop4h 51mAmerican Airlines
Deal found 9/13$229
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amMDW - LEX
1 stop5h 18mDelta
Wed 11/57:45 amLEX - MDW
1 stop5h 43mDelta
Deal found 9/14$271
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:00 amMDW - LEX
1 stop5h 15mDelta
Sat 10/410:24 amLEX - MDW
1 stop3h 04mDelta
Deal found 9/14$276

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.

Fly from

Chicago

Fly to

Lexington

Route

Depart

Return

Price

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 10/8

3:59 pm-6:30 pm

Nonstop1h 31m

Lexington Blue Grass

Sat 10/11

7:19 pm-8:02 pm

Nonstop1h 43m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Mon 10/13

9:25 pm-11:59 pm

Nonstop1h 34m

Lexington Blue Grass

Mon 10/20

7:33 pm-8:25 pm

Nonstop1h 52m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 11/14

8:01 am-10:33 am

Nonstop1h 32m

Lexington Blue Grass

Mon 11/17

6:58 pm-7:49 pm

Nonstop1h 51m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 10/15

8:17 am-10:42 am

Nonstop1h 25m

Lexington Blue Grass

Mon 10/20

7:19 pm-8:02 pm

Nonstop1h 43m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 10/10

8:45 pm-11:21 pm

Nonstop1h 36m

Lexington Blue Grass

Mon 10/13

7:19 pm-8:02 pm

Nonstop1h 43m

$190

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 10/8

6:15 pm-9:01 pm

Nonstop1h 46m

Lexington Blue Grass

Sun 10/12

7:33 pm-8:25 pm

Nonstop1h 52m

$193

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 9/30

2:47 pm-5:20 pm

Nonstop1h 33m

Lexington Blue Grass

Sat 10/4

7:33 pm-8:25 pm

Nonstop1h 52m

$199

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 10/10

6:15 pm-9:01 pm

Nonstop1h 46m

Lexington Blue Grass

Sun 10/12

7:33 pm-8:25 pm

Nonstop1h 52m

$210

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 9/30

9:50 am-2:57 pm

1 stop4h 07m

Lexington Blue Grass

Sat 10/4

5:48 pm-9:34 pm

1 stop4h 46m

$219

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 11/5

6:35 pm-3:06 pm

1 stop19h 31m

Lexington Blue Grass

Thu 11/6

6:58 pm-7:49 pm

Nonstop1h 51m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 40 results
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Best time to book a flight from Chicago to Lexington

Have a flexible travel schedule? Discover the best time to fly to Lexington from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Lexington

What is the cheapest month to book a flight from Chicago to Lexington?

Currently, August is the cheapest month in which you can book a flight from Chicago to Lexington (average of $303). Flying from Chicago to Lexington in April is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to LEX?

Find hourly flight availability from Chicago to Lexington. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to Lexington, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 13% versus a flight at noon.

What is the cheapest day to fly from Chicago to Lexington?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Lexington. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Lexington flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Lexington

Explore weekly flight availability from Chicago to Lexington. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from CHI to LEX are scheduled on a Monday (27 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (27 on average).

How much does it cost to fly round-trip from Chicago to Lexington?

Reviews of airlines servicing Lexington

Get insights into the airlines that provide service to Lexington. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Lexington. Reviews last updated September 15, 2025.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Lexington have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Lexington. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Lexington from Chicago?

    Most people fly into Lexington Blue Grass (LEX) if they book a flight to Lexington from Chicago. On average, Blue Grass has 27 inbound flights from Chicago per day from 2 airlines. Lexington Blue Grass is conveniently located just 5.6 mi from Lexington’s city center.

  • How long is the flight from Chicago to Lexington?

    Departing from Chicago to Lexington will take you 1h 31m. The distance from Chicago to Lexington is about 323 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Lexington round-trip?

    Currently priced at $189, American Airlines will fly you from Chicago to Lexington and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $189. American Airlines is priced at 30% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago to Lexington?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Lexington on time: GoJet (83%), United Airlines (72%), Air New Zealand (69%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $269, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Chicago O'Hare Intl - Lexington Blue Grass), you can expect to pay $189 for that flight.

  • Can I find deals for flights from Chicago to Lexington that include hotel bookings?

    Yes. In addition to deals on Chicago to Lexington flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Lexington?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Lexington.

  • Can I find deals for business class flights from Chicago to Lexington?

    Yes. Cheapflights offers flight deals from Chicago to Lexington by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Lexington?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Lexington (average of $303). Flying from Chicago to Lexington in April is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Georgetown
Berea
Frankfort

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Alternative routes for Chicago to Lexington

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Lexington

Discover the top 2 airlines that operate flights from Chicago to Lexington. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$359FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$269FlexibilityNo cancel feeOn-time71%

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