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Lexington

$101+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
nov. 20 — nov. 271
jue. 11/20
jue. 11/27
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 octubre 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$101
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$368

Good round-trip deal

$264 or less

Good one-way deal

$213 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. 14% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 21, 2025.

This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/149:18 pmORD - LEX
Nonstop1h 26mUnited Airlines
dom. 11/1610:40 amLEX - ORD
Nonstop1h 41mUnited Airlines
Deal found 10/20$189
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/33:54 pmORD - LEX
Nonstop1h 34mAmerican Airlines
mié. 12/106:58 pmLEX - ORD
Nonstop1h 52mAmerican Airlines
Deal found 10/19$191
This United Airlines deal was found by Cheapflights users on 10/19. 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.
mar. 11/46:15 pmORD - LEX
Nonstop1h 39mUnited Airlines
dom. 11/97:05 amLEX - ORD
Nonstop1h 49mUnited Airlines
Deal found 10/19$194
This American Airlines deal was found by Cheapflights users on 10/18. 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.
sáb. 11/18:45 pmORD - LEX
Nonstop1h 36mAmerican Airlines
mar. 11/46:40 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Deal found 10/18$199
This Delta deal was found by Cheapflights users on 10/20. 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.
jue. 12/181:14 pmMDW - LEX
1 stop3h 07mDelta
lun. 1/57:30 amLEX - MDW
1 stop6h 05mDelta
Deal found 10/20$209
This Delta deal was found by Cheapflights users on 10/20. 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.
mié. 11/125:23 amORD - LEX
1 stop5h 57mDelta
mié. 11/1910:12 amLEX - ORD
1 stop7h 34mDelta
Deal found 10/20$209
This Delta deal was found by Cheapflights users on 10/20. 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.
jue. 11/136:00 amMDW - LEX
1 stop5h 20mDelta
dom. 11/168:07 pmLEX - MDW
1 stop4h 33mDelta
Deal found 10/20$210
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/41:08 pmMDW - LEX
1 stop3h 00mDelta
dom. 11/98:07 pmLEX - MDW
1 stop4h 33mDelta
Deal found 10/19$214
This Delta deal was found by Cheapflights users on 10/20. 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.
mar. 11/41:08 pmMDW - LEX
1 stop3h 00mDelta
sáb. 11/86:00 amLEX - MDW
1 stop4h 40mDelta
Deal found 10/20$219
This Delta deal was found by Cheapflights users on 10/18. 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.
sáb. 11/14:09 pmORD - LEX
1 stop6h 56mDelta
mar. 11/410:05 amLEX - ORD
1 stop6h 00mDelta
Deal found 10/18$219
This Delta deal was found by Cheapflights users on 10/20. 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.
jue. 12/181:14 pmMDW - LEX
1 stop3h 07mDelta
mié. 12/316:20 amLEX - MDW
1 stop3h 29mDelta
Deal found 10/20$222
This Delta deal was found by Cheapflights users on 10/20. 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.
jue. 12/1810:45 amORD - LEX
1 stop5h 36mDelta
mar. 12/305:37 pmLEX - ORD
1 stop3h 59mDelta
Deal found 10/20$222

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 octubre 21, 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

mar. 11/18

9:18 pm-11:44 pm

Nonstop1h 26m

Lexington Blue Grass

mar. 11/25

7:05 am-7:54 am

Nonstop1h 49m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

vie. 11/21

3:59 pm-6:28 pm

Nonstop1h 29m

Lexington Blue Grass

lun. 11/24

6:00 am-6:44 am

Nonstop1h 44m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

vie. 11/14

9:18 pm-11:44 pm

Nonstop1h 26m

Lexington Blue Grass

dom. 11/16

10:40 am-11:21 am

Nonstop1h 41m

$189

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

mar. 11/4

10:45 am-1:17 pm

Nonstop1h 32m

Lexington Blue Grass

sáb. 11/8

5:45 pm-6:39 pm

Nonstop1h 54m

$199

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

mié. 12/3

12:50 pm-7:08 pm

1 stop5h 18m

Lexington Blue Grass

mié. 12/10

7:45 am-12:34 pm

1 stop5h 49m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

jue. 12/18

1:14 pm-5:21 pm

1 stop3h 07m

Lexington Blue Grass

sáb. 1/3

6:20 am-8:49 am

1 stop3h 29m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

jue. 12/18

10:45 am-5:21 pm

1 stop5h 36m

Lexington Blue Grass

sáb. 1/3

6:20 am-9:01 am

1 stop3h 41m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

vie. 11/21

1:14 pm-9:31 pm

1 stop7h 17m

Lexington Blue Grass

lun. 11/24

10:34 am-4:24 pm

1 stop6h 50m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

mar. 11/18

5:23 am-12:20 pm

1 stop5h 57m

Lexington Blue Grass

mar. 11/25

10:34 am-4:24 pm

1 stop6h 50m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

sáb. 12/13

10:45 am-5:31 pm

1 stop5h 46m

Lexington Blue Grass

dom. 12/14

7:59 pm-12:01 am

1 stop5h 02m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 39 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust 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

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

Currently, June is the cheapest month in which you can book a flight from Chicago to Lexington (average of $90). Flying from Chicago to Lexington in July is currently the most expensive (average of $189). 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 octubre 21, 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 at noon, 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 Tuesday afternoons when fares are most often at their lowest. Saturday afternoons 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 octubre 21, 2025.

The most flights from CHI to LEX are scheduled on a Monday (28 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

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 octubre 21, 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
8,991 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,991 reviews
United Airlines
7.4
Good
8,991 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,023 reviews
United Airlines
7.4
Good
8,991 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 26m. 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 31% 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: Emirates (91%), Avianca (85%), ANA (85%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $366, 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, June is the cheapest month in which you can book a flight from Chicago to Lexington (average of $90). Flying from Chicago to Lexington in July is currently the most expensive (average of $189). 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 octubre 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$368FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$268FlexibilityNo cancel feeOn-time71%

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