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Lexington

$156+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(American Airlines)

One-way from

$156
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$293

Good round-trip deal

$250 or less

Good one-way deal

$154 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. 5% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/29. 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 6/258:52 amORD - LEX
Nonstop1h 34mAmerican Airlines
Sat 6/286:54 pmLEX - ORD
Nonstop1h 35mAmerican Airlines
Deal found 3/29$189
This Delta deal was found by Cheapflights users on 3/30. 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.
Sat 5/104:25 pmORD - LEX
1 stop6h 26mDelta
Mon 5/127:59 pmLEX - ORD
1 stop4h 59mDelta
Deal found 3/30$209
This Delta deal was found by Cheapflights users on 3/30. 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 5/134:15 pmMDW - LEX
1 stop6h 36mDelta
Tue 5/2010:09 amLEX - MDW
1 stop6h 11mDelta
Deal found 3/30$229
This United Airlines deal was found by Cheapflights users on 3/29. 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 5/99:16 pmORD - LEX
Nonstop1h 30mUnited Airlines
Mon 5/126:10 pmLEX - ORD
Nonstop1h 45mUnited Airlines
Deal found 3/29$254
This Mytrip deal was found by Cheapflights users on 3/30. 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 5/49:30 amORD - LEX
1 stop9h 36mMultiple Airlines
Thu 5/82:14 pmLEX - ORD
1 stop16h 11mMultiple Airlines
Deal found 3/30$277

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 March 31, 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 6/25

8:52 am-11:26 am

Nonstop1h 34m

Lexington Blue Grass

Sat 6/28

6:54 pm-7:29 pm

Nonstop1h 35m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 5/10

4:25 pm-11:51 pm

1 stop6h 26m

Lexington Blue Grass

Mon 5/12

7:59 pm-11:58 pm

1 stop4h 59m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 5/13

4:15 pm-11:51 pm

1 stop6h 36m

Lexington Blue Grass

Tue 5/20

10:09 am-3:20 pm

1 stop6h 11m

$229

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Thu 7/17

9:14 pm-11:44 pm

Nonstop1h 30m

Lexington Blue Grass

Thu 7/24

7:00 am-7:51 am

Nonstop1h 51m

$254

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sun 5/4

9:30 am-8:06 pm

1 stop9h 36m

Lexington Blue Grass

Thu 5/8

2:14 pm-6:42 am

2 stops17h 28m

$299

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 4/19

7:55 am-1:24 pm

1 stop28h 29m

$156

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 5/28

6:00 am-9:51 pm

1 stop14h 51m

$187

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Mon 7/14

9:30 am-12:00 pm

Nonstop1h 30m

$214

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sun 4/6

6:10 pm-2:11 pm

1 stop19h 01m

$250

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 4/5

2:10 pm-4:42 pm

Nonstop1h 32m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 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

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 March 28, 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 March 31, 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 March 31, 2025.

The most flights from CHI to LEX are scheduled on a Sunday (23 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (8 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 March 31, 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
7,899 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
731 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
7,899 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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 15 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 $254, 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?

    $187 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $214 and $224, 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: Aer Lingus (88%), Qatar Airways (86%), Air Canada (84%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $529, 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?

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Alternative routes for Chicago to Lexington

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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$156Average$304FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$264FlexibilityNo cancel feeOn-time71%
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