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$102+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in May or January, booked 65 days in advance, depart on a Friday or Wednesday and return on a Saturday

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(American Airlines)

One-way from

$102
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$249

Good round-trip deal

$312 or less

Good one-way deal

$282 or less
Provider with most accurate pricing for Lexington Blue Grass-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Lexington Blue Grass-Chicago (CHI) flights.
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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. 1% potential increase in price ($3 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 October 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 October 29, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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 12/56:58 pmLEX - ORD
Nonstop1h 52mAmerican Airlines
Sun 12/78:35 pmORD - LEX
Nonstop1h 39mAmerican Airlines
Deal found 10/27$189
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/206:00 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Sun 11/238:05 amORD - LEX
Nonstop1h 32mAmerican Airlines
Deal found 10/27$190
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/146:58 pmLEX - ORD
Nonstop1h 51mAmerican Airlines
Mon 11/179:00 pmORD - LEX
Nonstop1h 38mAmerican Airlines
Deal found 10/27$195
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/146:58 pmLEX - ORD
Nonstop1h 51mAmerican Airlines
Sun 11/168:01 amORD - LEX
Nonstop1h 32mAmerican Airlines
Deal found 10/27$199
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 11/216:00 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Sat 11/298:04 amORD - LEX
Nonstop1h 32mAmerican Airlines
Deal found 10/29$202
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 11/166:00 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Mon 12/153:54 pmORD - LEX
Nonstop1h 34mAmerican Airlines
Deal found 10/29$204
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/236:00 amLEX - MDW
1 stop4h 52mDelta
Mon 12/155:29 pmMDW - LEX
1 stop5h 39mDelta
Deal found 10/29$209
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/231:05 pmLEX - ORD
1 stop4h 41mDelta
Wed 12/179:49 amORD - LEX
1 stop4h 07mDelta
Deal found 10/29$209
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/266:58 pmLEX - ORD
Nonstop1h 51mAmerican Airlines
Sat 11/298:04 amORD - LEX
Nonstop1h 32mAmerican Airlines
Deal found 10/29$217
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/1310:40 amLEX - ORD
Nonstop1h 41mUnited Airlines
Sat 11/154:20 pmORD - LEX
Nonstop1h 26mUnited Airlines
Deal found 10/29$219
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/256:00 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Mon 12/18:41 pmORD - LEX
Nonstop1h 40mAmerican Airlines
Deal found 10/28$222
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/216:00 amLEX - ORD
Nonstop1h 44mAmerican Airlines
Mon 11/248:41 pmORD - LEX
Nonstop1h 40mAmerican Airlines
Deal found 10/27$223

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 October 29, 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

Wed 11/26

5:45 pm-6:39 pm

Nonstop1h 54m

Chicago O'Hare Intl

Sat 11/29

4:40 pm-7:06 pm

Nonstop1h 26m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sun 11/16

6:00 am-6:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Mon 12/15

3:54 pm-6:28 pm

Nonstop1h 34m

$204

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sun 11/16

6:00 am-6:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Tue 12/16

8:35 pm-11:14 pm

Nonstop1h 39m

$204

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 12/5

7:45 am-12:34 pm

1 stop5h 49m

Chicago Midway

Sun 12/7

5:13 pm-12:08 am

1 stop5h 55m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sun 11/23

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Mon 12/15

5:29 pm-12:08 am

1 stop5h 39m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Mon 11/24

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Wed 12/17

10:49 am-4:28 pm

1 stop4h 39m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sun 11/23

1:05 pm-4:46 pm

1 stop4h 41m

Chicago O'Hare Intl

Wed 12/17

9:49 am-2:56 pm

1 stop4h 07m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 11/12

10:40 am-11:21 am

Nonstop1h 41m

Chicago O'Hare Intl

Mon 11/17

9:18 pm-11:44 pm

Nonstop1h 26m

$219

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 11/27

11:27 am-12:06 pm

Nonstop1h 39m

Chicago O'Hare Intl

Mon 12/1

8:41 pm-11:21 pm

Nonstop1h 40m

$222

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 2/3

2:00 pm-2:55 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 3/8

2:24 pm-4:55 pm

Nonstop1h 31m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 59 results
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Compare providers for flights from Lexington to Chicago

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 Lexington to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Lexington-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Lexington-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Lexington-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Lexington-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Lexington-Chicago 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 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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 65 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, January is the cheapest month in which you can book a flight from Lexington to Chicago (average of $73). Flying from Lexington to Chicago in July is currently the most expensive (average of $164). 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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Lexington to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 56% 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 Wednesday afternoons 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.

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 October 29, 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
8,999 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 19 flights from Blue Grass to Chicago per day from 2 different airlines.

  • How long is the flight from Lexington to Chicago?

    Airlines like United Airlines, American Airlines, and Delta fly from Lexington to Chicago in about 1h 44m. The time it takes to get you to your destination can typically vary by up to 4h 05m. 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 31% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Lexington to Chicago one-way?

    For one-way options, check prices for Allegiant Air. According to our data, you can fly for as low as $151. Users have also found prices from $214 and $214 on United Airlines and American Airlines, respectively.

  • 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: ANA (95%), Avianca (93%), Envoy Air (89%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $1,055 for a flight from Lexington to Chicago. The cheapest flight overall is $203 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, January is the cheapest month in which you can book a flight from Lexington to Chicago (average of $73). Flying from Lexington to Chicago in July is currently the most expensive (average of $164). 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
Porter
Benton Harbor

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$276FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$267FlexibilityNo cancel feeOn-time71%

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