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$122+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in February or October, 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 May 11, 2026.

This American Airlines deal was found by Cheapflights users on 5/6. 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 6/265:30 am
LEX
-
ORD
Nonstop1h 34m
American Airlines
Sun 6/2810:00 pm
ORD
-
LEX
Nonstop1h 30m
American Airlines
Deal found 5/6$249
This American Airlines deal was found by Cheapflights users on 5/10. 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 6/45:30 am
LEX
-
ORD
Nonstop1h 34m
American Airlines
Sun 6/78:59 pm
ORD
-
LEX
Nonstop1h 31m
American Airlines
Deal found 5/10$254
This American Airlines deal was found by Cheapflights users on 5/6. 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 7/105:01 pm
LEX
-
ORD
1 stop7h 29m
American Airlines
Mon 7/138:16 am
ORD
-
LEX
Nonstop1h 34m
American Airlines
Deal found 5/6$259
This American Airlines deal was found by Cheapflights users on 5/6. 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 5/225:19 am
LEX
-
ORD
Nonstop1h 36m
American Airlines
Sun 5/318:59 pm
ORD
-
LEX
Nonstop1h 34m
American Airlines
Deal found 5/6$264
This Delta deal was found by Cheapflights users on 5/10. 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.
Wed 6/107:35 am
LEX
-
MDW
1 stop6h 11m
Delta
Sat 6/134:25 pm
MDW
-
LEX
1 stop6h 39m
Delta
Deal found 5/10$269
This Delta deal was found by Cheapflights users on 5/6. 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 7/105:56 pm
LEX
-
ORD
1 stop6h 57m
Delta
Mon 7/133:22 pm
ORD
-
LEX
1 stop5h 42m
Delta
Deal found 5/6$269
This United Airlines deal was found by Cheapflights users on 5/10. 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 5/295:15 am
LEX
-
ORD
Nonstop1h 50m
United Airlines
Sat 5/3010:40 am
ORD
-
LEX
Nonstop1h 40m
United Airlines
Deal found 5/10$277
This United Airlines deal was found by Cheapflights users on 5/8. 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 5/227:00 am
LEX
-
ORD
Nonstop1h 50m
United Airlines
Sun 5/2410:40 am
ORD
-
LEX
Nonstop1h 40m
United Airlines
Deal found 5/8$279
This Delta deal was found by Cheapflights users on 5/6. 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 5/218:04 am
LEX
-
MDW
1 stop5h 38m
Delta
Wed 5/275:12 pm
MDW
-
LEX
1 stop5h 47m
Delta
Deal found 5/6$284
This American Airlines deal was found by Cheapflights users on 5/10. 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 5/294:35 pm
LEX
-
ORD
1 stop6h 02m
American Airlines
Sat 5/308:06 am
ORD
-
LEX
Nonstop1h 36m
American Airlines
Deal found 5/10$287
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/228:10 pm
LEX
-
ORD
1 stop4h 49m
American Airlines
Mon 5/258:06 am
ORD
-
LEX
Nonstop1h 36m
American Airlines
Deal found 5/5$289
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sun 12/136:14 pm
LEX
-
ORD
1 stop5h 40m
American Airlines
Wed 12/307:11 am
ORD
-
LEX
1 stop6h 16m
American Airlines
Deal found 5/10$292

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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$122
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$349

Good round-trip deal

$362 or less

Good one-way deal

$322 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. 13% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 11, 2026.
Use the filters below to find and compare flights from Lexington to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 5/21

7:00 am-7:52 am

Nonstop1h 52m

Chicago O'Hare Intl

Wed 5/27

7:00 am-9:30 am

Nonstop1h 30m

$264
Quickest round-trip

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 9/11

12:04 pm-12:40 pm

Nonstop1h 36m

Chicago O'Hare Intl

Sun 9/13

8:00 am-10:28 am

Nonstop1h 28m

$264

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 6/10

7:35 am-12:46 pm

1 stop6h 11m

Chicago Midway

Sat 6/13

4:25 pm-12:04 am

1 stop6h 39m

$269

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 7/10

7:35 am-12:38 pm

1 stop6h 03m

Chicago Midway

Mon 7/13

6:00 am-12:17 pm

1 stop5h 17m

$269

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 7/2

7:35 am-1:00 pm

1 stop6h 25m

Chicago O'Hare Intl

Sun 7/5

1:40 pm-9:19 pm

1 stop6h 39m

$269

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 7/15

7:35 am-1:03 pm

1 stop6h 28m

Chicago O'Hare Intl

Thu 7/23

6:35 am-12:17 pm

1 stop4h 42m

$269

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 5/29

5:15 am-6:05 am

Nonstop1h 50m

Chicago O'Hare Intl

Sat 5/30

10:40 am-1:20 pm

Nonstop1h 40m

$277

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 6/6

6:11 pm-9:53 pm

1 stop4h 42m

Chicago O'Hare Intl

Sat 6/13

11:15 am-5:18 pm

1 stop5h 03m

$279

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Mon 6/1

10:43 am-1:01 pm

1 stop3h 18m

Chicago O'Hare Intl

Mon 6/8

2:07 pm-9:19 pm

1 stop6h 12m

$279

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 6/5

8:20 pm-11:59 pm

1 stop4h 39m

Chicago O'Hare Intl

Fri 6/12

1:46 pm-10:03 pm

1 stop7h 17m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 51 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Lexington-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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?

To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 67 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, October is the cheapest month in which you can book a flight from Lexington to Chicago (average of $167). Flying from Lexington to Chicago in January 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 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 May 11, 2026.

A simple way to save on the total cost of your ticket is to fly from Lexington to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 38% 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 May 9, 2026.

Travelers seeking maximum savings on their Lexington to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday evenings 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 May 11, 2026.

The most flights from LEX to CHI are scheduled on a Monday (31 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (28 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 May 11, 2026.
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
9,699 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,699 reviews
United Airlines
7.4
Good
9,699 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,667 reviews
United Airlines
7.4
Good
9,699 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 30 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 36m. The time it takes to get you to your destination can typically vary by up to 4h 35m. 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 32% 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: PSA Airlines (83%), Japan Airlines (79%), Aer Lingus (77%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $780 for a flight from Lexington to Chicago. The cheapest flight overall is $268 while the most popular route, (Lexington Blue Grass - Chicago O'Hare Intl) is currently priced at $249.

  • 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, October is the cheapest month in which you can book a flight from Lexington to Chicago (average of $167). Flying from Lexington to Chicago in January 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$262FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$280FlexibilityNo cancel feeOn-time71%

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