HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Lexington

$123+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Lexington with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Lexington Blue Grass are usually found in January or December, booked 25 days in advance, depart on a Saturday or Thursday and return on a Friday

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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(American Airlines)

One-way from

$123
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$298

Good round-trip deal

$279 or less

Good one-way deal

$155 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. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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

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 April 24, 2025.

This United Airlines deal was found by Cheapflights users on 4/23. 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 5/219:16 pmORD - LEX
Nonstop1h 30mUnited Airlines
Wed 5/285:58 pmLEX - ORD
Nonstop1h 42mUnited Airlines
Deal found 4/23$189
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 6/74:00 pmORD - LEX
Nonstop1h 22mAmerican Airlines
Sat 6/1411:26 amLEX - ORD
Nonstop1h 35mAmerican Airlines
Deal found 4/23$190
This Delta deal was found by Cheapflights users on 4/23. 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 5/216:00 amMDW - LEX
1 stop5h 19mDelta
Wed 5/283:44 pmLEX - MDW
1 stop6h 43mDelta
Deal found 4/23$209
This Delta deal was found by Cheapflights users on 4/23. 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 5/157:10 amORD - LEX
1 stop3h 08mDelta
Mon 5/198:10 amLEX - ORD
1 stop5h 31mDelta
Deal found 4/23$209
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/85:05 amORD - LEX
1 stop13h 26mMultiple Airlines
Sun 6/159:58 amLEX - ORD
1 stop27h 41mMultiple Airlines
Deal found 4/23$284
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:36 pmMDW - LEX
2 stops24h 14mAllegiant Air
Fri 6/139:08 amLEX - MDW
2 stops11h 38mAllegiant Air
Deal found 4/23$402

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 April 24, 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 5/21

9:16 pm-11:46 pm

Nonstop1h 30m

Lexington Blue Grass

Wed 5/28

5:58 pm-6:40 pm

Nonstop1h 42m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 6/7

4:00 pm-6:22 pm

Nonstop1h 22m

Lexington Blue Grass

Sat 6/14

11:26 am-12:01 pm

Nonstop1h 35m

$190

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 5/21

6:00 am-12:19 pm

1 stop5h 19m

Lexington Blue Grass

Wed 5/28

3:44 pm-9:27 pm

1 stop6h 43m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Thu 5/15

7:10 am-11:18 am

1 stop3h 08m

Lexington Blue Grass

Mon 5/19

8:10 am-12:41 pm

1 stop5h 31m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sun 6/8

5:05 am-7:31 pm

1 stop13h 26m

Lexington Blue Grass

Sun 6/15

9:58 am-12:39 pm

1 stop27h 41m

$284

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 6/6

8:36 pm-9:50 pm

2 stops24h 14m

Lexington Blue Grass

Fri 6/13

9:08 am-7:46 pm

2 stops11h 38m

$402

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Mon 6/9

5:05 am-11:24 am

1 stop29h 19m

$131

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 5/13

8:04 am-10:30 am

Nonstop1h 26m

$134

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 5/13

12:48 pm-7:11 pm

1 stop5h 23m

$144

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 7/22

6:00 am-9:31 pm

2 stops14h 31m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 12 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 eDreams the most. eDreams 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

How far ahead should I book a flight from Chicago to Lexington?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Lexington. Price data was last updated on April 18, 2025.

The price you pay for your flight from Chicago to Lexington may vary depending on when you book. For the best chance of a lower fare, look to book 25 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 May is currently the most expensive (average of $398). 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 April 24, 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 morning, which can drop the price by up to 24% versus a flight in the afternoon.

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 Saturday evenings when fares are most often at their lowest. Monday evenings 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 April 24, 2025.

The most flights from CHI to LEX are scheduled on a Tuesday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

Rainfall in Lexington by month

Plan your trip to Lexington by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Lexington ranges from 2.9 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Lexington when rainfall is around 2.9 in.

Temperature in Lexington by month

Plan your trip to Lexington by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Lexington, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 April 24, 2025.
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 22 inbound flights from Chicago per day from 2 airlines. Lexington Blue Grass is conveniently located just 5.6 mi from Lexington’s city center.

  • 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. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $209 and $274, respectively. American Airlines is priced at 34% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Lexington one-way?

    $123 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and Allegiant Air, with prices starting from $144 and $167, respectively.

  • 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: SkyWest Airlines (89%), Air Canada (84%), Air New Zealand (80%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $532, our data shows the cheapest flight currently is $124. 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 May is currently the most expensive (average of $398). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Georgetown
Berea
Danville
Richmond

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Lexington

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Nashville flights
O'Hare Intl to Knoxville flights
O'Hare Intl to Cincinnati flights
Midway to Nashville flights
O'Hare Intl to Louisville flights
O'Hare Intl to Lexington flights
Midway to Knoxville flights
Midway to Cincinnati flights
St. Louis to Nashville flights
Moline to Nashville flights
Midway to Blountville flights
O'Hare Intl to Blountville flights
Midway to Louisville flights
Midway to Lexington flights
St. Louis to Knoxville flights
Moline to Louisville flights
O'Hare Intl to Evansville flights
Peoria to Nashville flights
St. Louis to Louisville flights
St. Louis to Blountville flights
Peoria to Knoxville flights
St. Louis to Lexington flights
St. Louis to Cincinnati flights
O'Hare Intl to Owensboro flights
Moline to Lexington flights
Moline to Knoxville flights
Springfield to Knoxville flights
O'Hare Intl to Paducah flights
O'Hare Intl to Huntington flights
Dubuque to Nashville flights
Moline to Cincinnati flights
Champaign to Nashville flights
Bloomington to Knoxville flights
Springfield to Nashville flights
St. Louis to Owensboro flights
Evansville to Cincinnati flights
Dubuque to Cincinnati flights
Dubuque to Lexington flights
Dubuque to Louisville flights
Dubuque to Knoxville flights
Peoria to Blountville flights
Springfield to Lexington flights

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$157Average$312FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$167Average$269FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.