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$120+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Lexington Blue Grass are usually found in January or December, booked 90 days in advance, depart on a Saturday or Thursday and return on a Saturday

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$158
(United Airlines)

One-way from

$130
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$328

Good round-trip deal

$222 or less

Good one-way deal

$214 or less
Provider with most accurate pricing for Chicago (CHI)-Lexington Blue Grass flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Lexington Blue Grass flights.
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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 ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. 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 5/66:00 pmORD - LEX
Nonstop1h 30mUnited Airlines
Wed 5/711:05 amLEX - ORD
Nonstop1h 43mUnited Airlines
Deal found 2/19$157
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 4/298:00 amORD - LEX
Nonstop1h 31mAmerican Airlines
Sat 5/35:05 pmLEX - ORD
Nonstop1h 35mAmerican Airlines
Deal found 2/20$172
This Delta deal was found by Cheapflights users on 2/20. 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 3/252:55 pmMDW - LEX
1 stop5h 37mDelta
Thu 3/277:30 amLEX - MDW
1 stop6h 06mDelta
Deal found 2/20$177
This Delta deal was found by Cheapflights users on 2/20. 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 4/166:45 amORD - LEX
1 stop3h 36mDelta
Wed 4/163:42 pmLEX - ORD
1 stop6h 08mDelta
Deal found 2/20$177
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 3/199:08 pmORD - LEX
1 stop22h 32mMultiple Airlines
Sun 3/233:20 pmLEX - ORD
1 stop26h 07mMultiple Airlines
Deal found 2/19$241

Find flights from Chicago to Lexington within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Lexington

Route

Depart

Return

Price

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 5/6

6:00 pm-8:30 pm

Nonstop1h 30m

Lexington Blue Grass

Wed 5/7

11:05 am-11:48 am

Nonstop1h 43m

$157

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 4/29

8:00 am-10:31 am

Nonstop1h 31m

Lexington Blue Grass

Sat 5/3

5:05 pm-5:40 pm

Nonstop1h 35m

$172

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 3/25

2:55 pm-9:32 pm

1 stop5h 37m

Lexington Blue Grass

Thu 3/27

7:30 am-12:36 pm

1 stop6h 06m

$177

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 4/16

6:45 am-11:21 am

1 stop3h 36m

Lexington Blue Grass

Wed 4/16

3:42 pm-8:50 pm

1 stop6h 08m

$177

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 3/19

9:08 pm-8:40 pm

1 stop22h 32m

Lexington Blue Grass

Sun 3/23

3:20 pm-4:27 pm

1 stop26h 07m

$241

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 3/19

7:21 pm-8:40 pm

2 stops24h 19m

$120

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 3/19

10:50 am-1:16 pm

Nonstop1h 26m

$130

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 4/30

3:02 pm-9:34 pm

1 stop5h 32m

$140

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Mon 3/17

10:25 am-5:19 pm

1 stop5h 54m

$140

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sun 3/2

6:20 pm-8:47 am

1 stop13h 27m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 11 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 February.
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.

Travel insights for flights from Chicago to Lexington

Get recent, data-driven insights about flights from Chicago to Lexington including ideal travel times, pricing trends, and more.

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 February 14, 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 89 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 February 20, 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 25% 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 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 February 20, 2025.

The most flights from CHI to LEX are scheduled on a Tuesday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 February 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and Allegiant Air from Chicago to Lexington by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

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
765 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

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
8,220 reviews

Crew

8.5

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

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 17 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 $158, United Airlines will fly you from Chicago to Lexington and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $172 and $177, respectively. United Airlines is priced at 44% 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?

    $130 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 $140 and $156, 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: Lufthansa (85%), Aer Lingus (80%), Avianca (77%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $258, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago O'Hare Intl - Lexington Blue Grass), you can expect to pay $157 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

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$256FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$154Average$290FlexibilityNo cancel feeOn-time69%
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