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$105+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$189
(United Airlines)

One-way from

$105
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$245

Good round-trip deal

$189 or less

Good one-way deal

$213 or less
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. 3% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/58:10 amORD - LEX
Nonstop1h 29mAmerican Airlines
Sat 9/611:09 amLEX - ORD
Nonstop1h 38mAmerican Airlines
Deal found 6/30$189
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 8/156:04 amMDW - LEX
1 stop5h 14mDelta
Sun 8/177:45 amLEX - MDW
1 stop5h 43mDelta
Deal found 6/30$209
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/155:45 amORD - LEX
1 stop5h 33mDelta
Sun 8/177:45 amLEX - ORD
1 stop3h 35mDelta
Deal found 6/29$209
This United Airlines deal was found by Cheapflights users on 7/2. 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 10/316:15 pmORD - LEX
Nonstop1h 39mUnited Airlines
Sun 11/21:59 pmLEX - ORD
Nonstop1h 43mUnited Airlines
Deal found 7/2$216
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 8/84:37 pmORD - LEX
2 stops19h 22mMultiple Airlines
Sun 8/107:34 pmLEX - ORD
1 stop14h 21mMultiple Airlines
Deal found 6/30$235
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 8/152:54 pmMDW - LEX
2 stops18h 16mAllegiant Air
Sun 8/177:47 pmLEX - MDW
2 stops23h 30mAllegiant Air
Deal found 6/30$300

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 July 2, 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

Fri 9/5

8:10 am-10:39 am

Nonstop1h 29m

Lexington Blue Grass

Sat 9/6

11:09 am-11:47 am

Nonstop1h 38m

$189

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 8/15

6:04 am-12:18 pm

1 stop5h 14m

Lexington Blue Grass

Sun 8/17

7:45 am-12:28 pm

1 stop5h 43m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 8/15

5:45 am-12:18 pm

1 stop5h 33m

Lexington Blue Grass

Sun 8/17

7:45 am-10:20 am

1 stop3h 35m

$209

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 10/31

6:15 pm-8:54 pm

Nonstop1h 39m

Lexington Blue Grass

Sun 11/2

1:59 pm-2:42 pm

Nonstop1h 43m

$216

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 8/8

4:37 pm-12:59 pm

2 stops19h 22m

Lexington Blue Grass

Sun 8/10

7:34 pm-8:55 am

1 stop14h 21m

$235

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Fri 8/15

2:54 pm-10:10 am

2 stops18h 16m

Lexington Blue Grass

Sun 8/17

7:47 pm-6:17 pm

2 stops23h 30m

$300

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 7/25

4:36 pm-7:54 am

1 stop14h 18m

$105

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 10/9

5:40 pm-8:17 am

1 stop13h 37m

$118

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Thu 7/31

4:18 pm-6:42 pm

Nonstop1h 24m

$208

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 7/29

1:09 pm-5:07 pm

1 stop2h 58m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 12 results
1
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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, 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 April is currently the most expensive (average of $390). 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 July 2, 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 11% 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. 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 July 2, 2025.

The most flights from CHI to LEX are scheduled on a Tuesday (27 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (8 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 July 2, 2025.
See what other customers who have flown with Delta, 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.
Delta
8.0
Very good
7,975 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,975 reviews
Delta
8.0
Very good
7,975 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,975 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,975 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.2
Good
709 reviews
Delta
8.0
Very good
7,975 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 19 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, 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 $190 and $209, respectively. United Airlines is priced at 31% 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?

    $118 is the cheapest one-way deal found within the past few days, from Allegiant Air. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $208 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: Envoy Air (82%), Avianca (80%), ANA (80%).

  • What are the cheapest flights from Chicago to Lexington?

    While on average a flight from Chicago to Lexington is generally $246, our data shows the cheapest flight currently is $189. 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 April is currently the most expensive (average of $390). 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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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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$157Average$333FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$266FlexibilityNo cancel feeOn-time71%

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