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$110+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
apr 22 — apr 291
mer 4/22
mer 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in February 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 marzo 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
gio 4/239:31 am
LEX
-
ORD
1 stop12h 46m
Multiple Airlines
mer 4/291:27 pm
ORD
-
LEX
1 stop18h 14m
Multiple Airlines
Deal found 3/18$213
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
lun 4/279:45 pm
LEX
-
ORD
1 stop16h 15m
Multiple Airlines
mer 4/297:15 pm
ORD
-
LEX
1 stop12h 26m
Multiple Airlines
Deal found 3/20$233
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
gio 4/239:31 am
LEX
-
ORD
1 stop15h 53m
Multiple Airlines
sab 4/257:15 pm
ORD
-
LEX
1 stop12h 26m
Multiple Airlines
Deal found 3/18$235
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
gio 4/309:31 am
LEX
-
MDW
2 stops13h 48m
Multiple Airlines
dom 5/39:16 am
MDW
-
LEX
1 stop22h 26m
Multiple Airlines
Deal found 3/20$248
This United Airlines deal was found by Cheapflights users on 3/22. 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.
sab 5/166:03 pm
LEX
-
ORD
Nonstop1h 48m
United Airlines
lun 5/184:20 pm
ORD
-
LEX
Nonstop1h 29m
United Airlines
Deal found 3/22$249
This American Airlines deal was found by Cheapflights users on 3/18. 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.
mer 5/131:14 pm
LEX
-
ORD
Nonstop1h 45m
American Airlines
ven 5/228:06 am
ORD
-
LEX
Nonstop1h 36m
American Airlines
Deal found 3/18$251
This American Airlines deal was found by Cheapflights users on 3/22. 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.
ven 4/171:14 pm
LEX
-
ORD
Nonstop1h 45m
American Airlines
dom 4/199:06 pm
ORD
-
LEX
Nonstop1h 32m
American Airlines
Deal found 3/22$252
This American Airlines deal was found by Cheapflights users on 3/22. 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.
mar 4/214:27 pm
LEX
-
ORD
Nonstop1h 51m
American Airlines
mar 4/289:06 pm
ORD
-
LEX
Nonstop1h 32m
American Airlines
Deal found 3/22$255
This United Airlines deal was found by Cheapflights users on 3/19. 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.
mer 6/37:00 am
LEX
-
ORD
Nonstop1h 50m
United Airlines
dom 6/79:20 pm
ORD
-
LEX
Nonstop1h 39m
United Airlines
Deal found 3/19$258
This American Airlines deal was found by Cheapflights users on 3/20. 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.
ven 4/244:27 pm
LEX
-
ORD
Nonstop1h 51m
American Airlines
lun 4/273:31 pm
ORD
-
LEX
1 stop7h 21m
American Airlines
Deal found 3/20$259
This Delta deal was found by Cheapflights users on 3/22. 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.
mar 4/2110:22 am
LEX
-
MDW
1 stop7h 04m
Delta
mar 4/286:00 am
MDW
-
LEX
1 stop6h 34m
Delta
Deal found 3/22$269
This Delta deal was found by Cheapflights users on 3/20. 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.
ven 4/37:45 am
LEX
-
MDW
1 stop5h 44m
Delta
lun 4/61:10 pm
MDW
-
LEX
1 stop2h 57m
Delta
Deal found 3/20$299

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 marzo 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$233
(Kiwi.com)

One-way from

$110
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$294

Good round-trip deal

$372 or less

Good one-way deal

$288 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. 2% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 marzo 23, 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

gio 4/23

9:00 pm-9:47 pm

Nonstop1h 47m

Chicago O'Hare Intl

dom 4/26

7:55 pm-10:29 pm

Nonstop1h 34m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

mer 5/13

8:50 am-9:42 am

Nonstop1h 52m

Chicago O'Hare Intl

ven 5/22

4:32 pm-7:09 pm

Nonstop1h 37m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

gio 5/7

10:10 am-11:02 am

Nonstop1h 52m

Chicago O'Hare Intl

dom 5/10

6:55 am-9:20 am

Nonstop1h 25m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

ven 5/8

7:00 am-7:50 am

Nonstop1h 50m

Chicago O'Hare Intl

dom 5/10

4:20 pm-6:49 pm

Nonstop1h 29m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

mer 7/29

10:12 am-11:00 am

Nonstop1h 48m

Chicago O'Hare Intl

dom 8/2

6:45 am-9:16 am

Nonstop1h 31m

$249
Quickest round-trip

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

lun 4/20

9:00 pm-9:47 pm

Nonstop1h 47m

Chicago O'Hare Intl

lun 4/27

6:55 am-9:20 am

Nonstop1h 25m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

gio 4/16

9:00 pm-9:47 pm

Nonstop1h 47m

Chicago O'Hare Intl

gio 4/23

9:30 pm-11:59 pm

Nonstop1h 29m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

gio 7/2

7:44 pm-8:35 pm

Nonstop1h 51m

Chicago O'Hare Intl

sab 7/4

7:54 pm-10:35 pm

Nonstop1h 41m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

mer 7/8

8:50 am-9:35 am

Nonstop1h 45m

Chicago O'Hare Intl

dom 7/12

6:45 am-9:16 am

Nonstop1h 31m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

mar 4/21

4:27 pm-5:18 pm

Nonstop1h 51m

Chicago O'Hare Intl

mar 4/28

9:06 pm-11:38 pm

Nonstop1h 32m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 48 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 March.
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?

Use this chart to determine the optimal time to book a round-trip flight from Lexington to Chicago. Price data was last updated on March 13, 2026.

To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 21 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, September is the cheapest month in which you can book a flight from Lexington to Chicago (average of $77). Flying from Lexington to Chicago in February is currently the most expensive (average of $204). 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 marzo 23, 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 39% 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 March 23, 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 marzo 23, 2026.

The most flights from LEX to CHI are scheduled on a Wednesday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (22 on average).

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 marzo 23, 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
9,460 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,460 reviews
United Airlines
7.4
Good
9,460 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,489 reviews
United Airlines
7.4
Good
9,460 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 27 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, Delta, and Allegiant Air fly from Lexington to Chicago in about 1h 47m. The time it takes to get you to your destination can typically vary by up to 24h 41m. 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 29% 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: Air Canada (78%), Lufthansa (77%), Avianca (76%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $894 for a flight from Lexington to Chicago. The cheapest flight overall is $220 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, September is the cheapest month in which you can book a flight from Lexington to Chicago (average of $77). Flying from Lexington to Chicago in February is currently the most expensive (average of $204). 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 marzo 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$258FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$280FlexibilityNo cancel feeOn-time71%

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