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$106+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in January or May, booked 75 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap 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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amLEX - ORD
Nonstop1h 55mUnited Airlines
Thu 1/12:33 pmORD - LEX
Nonstop1h 32mUnited Airlines
Deal found 12/10$202
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:57 pmLEX - ORD
Nonstop1h 57mUnited Airlines
Fri 1/210:35 amORD - LEX
Nonstop1h 41mUnited Airlines
Deal found 12/10$204
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:57 pmLEX - ORD
Nonstop1h 57mUnited Airlines
Tue 12/302:33 pmORD - LEX
Nonstop1h 32mUnited Airlines
Deal found 12/10$217
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Fri 12/268:04 amLEX - ORD
Nonstop1h 40mAmerican Airlines
Tue 12/308:37 pmORD - LEX
Nonstop1h 35mAmerican Airlines
Deal found 12/10$219
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Sun 12/216:00 amLEX - ORD
Nonstop1h 55mUnited Airlines
Sun 1/188:05 pmORD - LEX
Nonstop1h 35mUnited Airlines
Deal found 12/9$234
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Wed 12/1711:04 amLEX - ORD
Nonstop1h 39mAmerican Airlines
Mon 1/121:45 pmORD - LEX
Nonstop1h 29mAmerican Airlines
Deal found 12/11$237
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Sun 12/216:09 amLEX - ORD
1 stop7h 31mAmerican Airlines
Sun 1/188:54 pmORD - LEX
Nonstop1h 29mAmerican Airlines
Deal found 12/11$244
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/258:08 amLEX - ORD
1 stop7h 04mAmerican Airlines
Tue 12/308:37 pmORD - LEX
Nonstop1h 35mAmerican Airlines
Deal found 12/10$259
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Sun 12/146:00 amLEX - ORD
Nonstop1h 39mAmerican Airlines
Thu 1/88:54 pmORD - LEX
Nonstop1h 29mAmerican Airlines
Deal found 12/11$266
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:20 amLEX - MDW
1 stop3h 29mDelta
Tue 12/306:08 pmMDW - LEX
1 stop3h 59mDelta
Deal found 12/10$269
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 12/1511:04 amLEX - ORD
Nonstop1h 39mAmerican Airlines
Sat 1/311:25 pmORD - LEX
Nonstop1h 30mAmerican Airlines
Deal found 12/10$271
This Delta deal was found by Cheapflights users on 12/11. 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.
Sun 12/146:05 amLEX - MDW
1 stop6h 50mDelta
Thu 1/89:32 amMDW - LEX
1 stop6h 22mDelta
Deal found 12/11$286

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$106
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$294

Good round-trip deal

$329 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Lexington Blue Grass-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lexington Blue Grass-Chicago (CHI) flights.
Search Deals
From Lexington Blue Grass to Chicago (CHI)
Search Deals
One-way flight from Lexington Blue Grass to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Lexington Blue Grass to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Lexington Blue Grass to Chicago (CHI).
Search Deals

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 December 12, 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

Sun 1/4

10:13 pm-10:56 pm

Nonstop1h 43m

Chicago O'Hare Intl

Sun 1/18

8:54 pm-11:23 pm

Nonstop1h 29m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Mon 1/12

8:35 am-9:30 am

Nonstop1h 55m

Chicago O'Hare Intl

Mon 1/19

2:15 pm-4:48 pm

Nonstop1h 33m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 1/16

5:32 pm-6:29 pm

Nonstop1h 57m

Chicago O'Hare Intl

Mon 1/19

8:05 pm-10:40 pm

Nonstop1h 35m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Mon 2/2

4:58 pm-5:49 pm

Nonstop1h 51m

Chicago O'Hare Intl

Tue 2/17

8:55 pm-11:15 pm

Nonstop1h 20m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 1/14

8:35 am-9:30 am

Nonstop1h 55m

Chicago O'Hare Intl

Sat 1/17

5:59 pm-8:31 pm

Nonstop1h 32m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 1/29

4:58 pm-5:49 pm

Nonstop1h 51m

Chicago O'Hare Intl

Mon 2/2

8:54 pm-11:23 pm

Nonstop1h 29m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 2/13

7:00 am-7:46 am

Nonstop1h 46m

Chicago O'Hare Intl

Sun 2/15

9:25 pm-11:50 pm

Nonstop1h 25m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 1/8

5:32 pm-6:29 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sat 1/10

2:31 pm-5:04 pm

Nonstop1h 33m

$198

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 12/25

6:00 am-6:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Thu 1/1

2:33 pm-5:05 pm

Nonstop1h 32m

$202

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 2/20

5:02 pm-5:43 pm

Nonstop1h 41m

Chicago O'Hare Intl

Mon 2/23

8:54 pm-11:14 pm

Nonstop1h 20m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 48 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 December.
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 December 5, 2025.

To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 46 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 $167). 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 December 12, 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 55% 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.

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 December 12, 2025.

The most flights from LEX to CHI are scheduled on a Thursday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 December 12, 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
9,095 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,095 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 23 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 43m. The time it takes to get you to your destination can typically vary by up to 3h 10m. 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 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: Envoy Air (95%), ANA (87%), Avianca (78%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $876 for a flight from Lexington to Chicago. The cheapest flight overall is $144 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 $167). 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
Lansing
Merrillville
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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$276FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$274FlexibilityNo cancel feeOn-time71%

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