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$111+ Cheap flights from Lexington (LEX) to Chicago (CHI)

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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in November or September, booked 82 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Lexington to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Lexington (LEX) to Chicago (CHI). 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 September 11, 2025.

Round-trip from

$189
(United Airlines)

One-way from

$111
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$234

Good round-trip deal

$294 or less

Good one-way deal

$236 or less
From Lexington Blue Grass to Chicago (CHI)
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One-way flight from Lexington Blue Grass to Chicago (CHI)
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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. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Lexington Blue Grass to Chicago (CHI).
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Price to beat on a one-way flight from Lexington Blue Grass to Chicago (CHI).
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Find flight deals from Lexington to Chicago

Cheapest flights from Lexington to Chicago
Explore the most affordable flight options available from Lexington to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/1110:37 amLEX - ORD
Nonstop1h 44mUnited Airlines
Sat 10/182:47 pmORD - LEX
Nonstop1h 33mUnited Airlines
Deal found 9/11$189
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 10/211:09 amLEX - ORD
Nonstop1h 38mAmerican Airlines
Mon 10/68:45 pmORD - LEX
Nonstop1h 36mAmerican Airlines
Deal found 9/9$190
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 10/97:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Mon 10/139:25 pmORD - LEX
Nonstop1h 34mUnited Airlines
Deal found 9/9$194
This United Airlines deal was found by Cheapflights users on 9/11. 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 9/267:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Mon 9/291:15 pmORD - LEX
Nonstop1h 33mUnited Airlines
Deal found 9/11$199
This Delta deal was found by Cheapflights users on 9/11. 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 11/225:35 pmLEX - MDW
1 stop6h 57mDelta
Mon 11/245:34 pmMDW - LEX
1 stop5h 30mDelta
Deal found 9/11$209
This Delta deal was found by Cheapflights users on 9/11. 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 11/17:45 amLEX - ORD
1 stop5h 55mDelta
Tue 11/44:15 pmORD - LEX
1 stop6h 50mDelta
Deal found 9/11$209
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/17:33 pmLEX - ORD
Nonstop1h 52mUnited Airlines
Sat 10/411:03 amORD - LEX
Nonstop1h 31mUnited Airlines
Deal found 9/9$210
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/25:55 amLEX - ORD
Nonstop1h 36mAmerican Airlines
Sun 10/58:10 amORD - LEX
Nonstop1h 29mAmerican Airlines
Deal found 9/10$219
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/246:50 amLEX - ORD
Nonstop1h 39mAmerican Airlines
Tue 10/288:17 amORD - LEX
Nonstop1h 25mAmerican Airlines
Deal found 9/11$222
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/166:34 pmLEX - ORD
Nonstop1h 44mAmerican Airlines
Tue 9/238:10 amORD - LEX
Nonstop1h 29mAmerican Airlines
Deal found 9/9$224
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/115:59 pmLEX - ORD
1 stop4h 25mAmerican Airlines
Sat 10/188:17 amORD - LEX
Nonstop1h 25mAmerican Airlines
Deal found 9/11$229
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:25 pmLEX - ORD
1 stop16h 27mMultiple Airlines
Mon 10/66:18 pmORD - LEX
1 stop25h 32mMultiple Airlines
Deal found 9/9$233

Cheapflights Fare Finder

 
Customize your flight search to find flights from Lexington to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Lexington to Chicago that are best for you.

Fly from

Lexington

Fly to

Chicago

Route

Depart

Return

Price

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 11/1

6:50 am-7:29 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 11/2

8:01 am-10:33 am

Nonstop1h 32m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 10/8

7:33 pm-8:25 pm

Nonstop1h 52m

Chicago O'Hare Intl

Wed 10/15

1:15 pm-3:48 pm

Nonstop1h 33m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 10/7

7:05 am-7:49 am

Nonstop1h 44m

Chicago O'Hare Intl

Tue 10/14

9:25 pm-11:59 pm

Nonstop1h 34m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 10/31

7:46 am-8:25 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 11/2

8:01 am-10:33 am

Nonstop1h 32m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 10/21

6:50 am-7:29 am

Nonstop1h 39m

Chicago O'Hare Intl

Tue 2/24

1:10 pm-3:35 pm

Nonstop1h 25m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 10/11

7:33 pm-8:25 pm

Nonstop1h 52m

Chicago O'Hare Intl

Mon 10/13

9:25 pm-11:59 pm

Nonstop1h 34m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 10/24

7:33 pm-8:25 pm

Nonstop1h 52m

Chicago O'Hare Intl

Thu 10/30

2:40 pm-5:10 pm

Nonstop1h 30m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 10/23

6:50 am-7:29 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 10/26

8:17 am-10:42 am

Nonstop1h 25m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 10/31

7:05 am-7:54 am

Nonstop1h 49m

Chicago O'Hare Intl

Sun 11/2

10:45 am-1:17 pm

Nonstop1h 32m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 10/11

10:37 am-11:21 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 10/18

2:47 pm-5:20 pm

Nonstop1h 33m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 48 results
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5

Best time to book a flight from Lexington to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Lexington 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 Lexington to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Lexington to Chicago. Price data was last updated on August 29, 2025.

To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Lexington to Chicago (average of $245). Flying from Lexington to Chicago in March is currently the most expensive (average of $321). 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 LEX to CHI?

Find hourly flight availability from Lexington to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Lexington to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Lexington to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Lexington to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Lexington to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Lexington to Chicago

Explore weekly flight availability from Lexington to Chicago. 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 September 11, 2025.

The most flights from LEX to CHI are scheduled on a Wednesday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

How much does it cost to fly round-trip from Lexington to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Lexington to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Lexington to Chicago. 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 from for flights from Lexington to Chicago?

    If you book a flight to Chicago from Lexington, you will be flying from Blue Grass, which is the city’s only airport. Lexington Blue Grass (LEX) is located 5.6 mi from the center of Lexington. There are 25 flights from Blue Grass to Chicago per day from 2 different airlines.

  • How long is the flight from Lexington to Chicago?

    Airlines like American Airlines, United Airlines, and Delta fly from Lexington to Chicago in about 1h 39m. The time it takes to get you to your destination can typically vary by up to 5h 18m. Lexington and Chicago are separated by a distance of 323 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Lexington to Chicago round-trip?

    American Airlines, at $189, was found to be the cheapest airline from Lexington to Chicago. An alternate airline flying to your destination would be United Airlines. American Airlines is currently priced 30% below the average price you’ll pay for this route.

  • What are the most popular routes from Lexington to Chicago?

    The most popular flight routes from Lexington to Chicago are Lexington Blue Grass - Chicago O'Hare Intl, Lexington Blue Grass - Chicago Midway and Lexington Blue Grass - Chicago Greater Rockford.

  • What are the most reliable airlines from Lexington to Chicago?

    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 Lexington to Chicago on time: Avianca (90%), ANA (90%), United Airlines (77%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $981 for a flight from Lexington to Chicago. The cheapest flight overall is $171 while the most popular route, (Lexington Blue Grass - Chicago O'Hare Intl) is currently priced at $189.

  • Can I find deals for flights from Lexington to Chicago that include hotel bookings?

    Yes. In addition to deals on Lexington to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Lexington to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Lexington to Chicago.

  • Can I find deals for business class flights from Lexington to Chicago?

    Yes. Cheapflights offers flight deals from Lexington to Chicago 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 Lexington to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Lexington to Chicago (average of $245). Flying from Lexington to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Lexington to Chicago

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Top 2 airlines flying from Lexington to Chicago

Discover the top 2 airlines that operate flights from Lexington to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$279FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$266FlexibilityNo cancel feeOn-time71%

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