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Lexington

$169+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
1 adult, Economy
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Cheap 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 May 29, 2026.

This American Airlines deal was found by Cheapflights users on 5/28. 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 11/63:52 pm
ORD
-
LEX
Nonstop1h 29m
American Airlines
Sun 11/86:51 pm
LEX
-
ORD
Nonstop1h 51m
American Airlines
Deal found 5/28$249
This American Airlines deal was found by Cheapflights users on 5/27. 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 6/1810:00 pm
ORD
-
LEX
Nonstop1h 30m
American Airlines
Sun 6/216:30 pm
LEX
-
ORD
Nonstop1h 59m
American Airlines
Deal found 5/27$250
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/2510:00 pm
ORD
-
LEX
Nonstop1h 30m
American Airlines
Thu 7/25:00 am
LEX
-
ORD
1 stop5h 02m
American Airlines
Deal found 5/28$259
This American Airlines deal was found by Cheapflights users on 5/26. 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 6/113:23 pm
ORD
-
LEX
Nonstop1h 35m
American Airlines
Thu 6/185:30 am
LEX
-
ORD
Nonstop1h 34m
American Airlines
Deal found 5/26$264
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 7/106:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Fri 7/245:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 5/28$269
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 7/106:35 am
ORD
-
LEX
1 stop4h 42m
Delta
Tue 7/215:56 pm
LEX
-
ORD
1 stop6h 57m
Delta
Deal found 5/28$269
This Delta deal was found by Cheapflights users on 5/27. 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.
Thu 6/182:07 pm
ORD
-
LEX
1 stop6h 12m
Delta
Sun 6/217:35 am
LEX
-
ORD
1 stop6h 29m
Delta
Deal found 5/27$270
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Thu 6/119:20 pm
ORD
-
LEX
Nonstop1h 39m
United Airlines
Sun 6/147:00 am
LEX
-
ORD
Nonstop1h 50m
United Airlines
Deal found 5/28$279
This Delta deal was found by Cheapflights users on 5/26. 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.
Fri 7/36:00 am
MDW
-
LEX
1 stop5h 19m
Delta
Sat 7/118:00 am
LEX
-
MDW
1 stop5h 38m
Delta
Deal found 5/26$282
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 7/106:00 am
MDW
-
LEX
1 stop5h 17m
Delta
Thu 7/235:56 pm
LEX
-
MDW
1 stop5h 19m
Delta
Deal found 5/28$284
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 6/112:07 pm
ORD
-
LEX
1 stop6h 12m
Delta
Sun 6/147:35 am
LEX
-
ORD
1 stop6h 29m
Delta
Deal found 5/24$284
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/1110:00 pm
ORD
-
LEX
Nonstop1h 30m
American Airlines
Sun 6/145:00 am
LEX
-
ORD
1 stop7h 00m
American Airlines
Deal found 5/28$289

Find 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 May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$169
(American Airlines)

Popular in

February

Cheapest in

July

Average price

$339

Good round-trip deal

$259 or less

Good one-way deal

$359 or less
Provider with most accurate pricing for Chicago (CHI)-Lexington Blue Grass flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Lexington Blue Grass flights.
Search Deals
From Chicago (CHI) to Lexington Blue Grass
Search Deals
One-way flight from Chicago (CHI) to Lexington Blue Grass
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Lexington Blue Grass.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Lexington Blue Grass.
Search Deals

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 May 29, 2026.
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

Cheapest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 7/3

9:20 pm-11:59 pm

Nonstop1h 39m

Lexington Blue Grass

Mon 7/6

7:00 am-7:52 am

Nonstop1h 52m

$249

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 8/29

5:50 pm-8:28 pm

Nonstop1h 38m

Lexington Blue Grass

Sun 8/30

9:52 am-10:40 am

Nonstop1h 48m

$249
Quickest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 8/12

9:20 pm-11:55 pm

Nonstop1h 35m

Lexington Blue Grass

Sat 8/15

7:00 am-7:45 am

Nonstop1h 45m

$249

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 7/30

5:10 pm-11:55 pm

1 stop5h 45m

Lexington Blue Grass

Sat 8/8

7:35 am-12:39 pm

1 stop6h 04m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 7/4

4:25 pm-12:04 am

1 stop6h 39m

Lexington Blue Grass

Thu 7/9

7:35 am-12:38 pm

1 stop6h 03m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 7/10

6:00 am-12:17 pm

1 stop5h 17m

Lexington Blue Grass

Fri 7/24

5:56 pm-10:15 pm

1 stop5h 19m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 8/29

6:05 am-12:11 pm

1 stop5h 06m

Lexington Blue Grass

Sun 8/30

6:00 am-9:59 am

1 stop4h 59m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 8/28

5:10 pm-11:59 pm

1 stop5h 49m

Lexington Blue Grass

Sun 8/30

6:00 am-11:51 am

1 stop6h 51m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 6/25

6:00 am-12:19 pm

1 stop5h 19m

Lexington Blue Grass

Sun 6/28

7:35 am-12:46 pm

1 stop6h 11m

$269

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 8/14

6:05 am-12:11 pm

1 stop5h 06m

Lexington Blue Grass

Sun 8/16

7:35 am-12:39 pm

1 stop6h 04m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/29

Showing 1-10 of 43 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Lexington

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Lexington in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Lexington flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Lexington flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Lexington flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Lexington flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Lexington flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, January is the cheapest month in which you can book a flight from Chicago to Lexington (average of $162). Flying from Chicago to Lexington in May is currently the most expensive (average of $229). 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 May 29, 2026.

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 morning, which can drop the price by up to 30% versus a flight at noon.

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 May 29, 2026.

The most flights from CHI to LEX are scheduled on a Thursday (28 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 on average).

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

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 May 23, 2026.

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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 29, 2026.
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
9,763 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,763 reviews
United Airlines
7.4
Good
9,763 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,643 reviews
United Airlines
7.4
Good
9,763 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 23 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 39m. 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 44% 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: Qatar Airways (84%), Envoy Air (80%), Alaska Airlines (78%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $374, our data shows the cheapest flight currently is $168. When looking at the most popular route, (Chicago O'Hare Intl - Lexington Blue Grass), you can expect to pay $249 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, January is the cheapest month in which you can book a flight from Chicago to Lexington (average of $162). Flying from Chicago to Lexington in May is currently the most expensive (average of $229). 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
Somerset
Danville
Berea
Frankfort
Georgetown

Browse thousands of different options on Cheapflights for your next trip

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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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$270FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$377FlexibilityNo cancel feeOn-time69%

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