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$154+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in September or November, booked 82 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Mytrip)

One-way from

$154
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$278

Good round-trip deal

$330 or less

Good one-way deal

$265 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. 16% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2712:19 pmLEX - ORD
1 stop21h 31mMultiple Airlines
Thu 5/296:30 amORD - LEX
1 stop24h 48mMultiple Airlines
Deal found 4/30$208
This Delta deal was found by Cheapflights users on 4/29. 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.
Wed 6/118:06 amLEX - MDW
1 stop5h 23mDelta
Wed 8/271:00 pmMDW - LEX
1 stop3h 07mDelta
Deal found 4/29$209
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/225:49 pmLEX - ORD
1 stop3h 32mDelta
Sun 5/257:10 amORD - LEX
1 stop3h 08mDelta
Deal found 4/29$209
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/156:48 pmLEX - ORD
Nonstop1h 35mAmerican Airlines
Sat 6/218:45 pmORD - LEX
Nonstop1h 43mAmerican Airlines
Deal found 4/29$217
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/136:10 pmLEX - ORD
Nonstop1h 45mUnited Airlines
Tue 5/202:58 pmORD - LEX
Nonstop1h 31mUnited Airlines
Deal found 4/29$254
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/119:13 pmLEX - RFD
1 stop13h 39mAllegiant Air
Wed 8/276:03 pmRFD - LEX
1 stop24h 34mAllegiant Air
Deal found 4/29$278

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 1, 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

Tue 5/27

12:19 pm-8:50 am

1 stop21h 31m

Chicago O'Hare Intl

Thu 5/29

6:30 am-8:18 am

1 stop24h 48m

$208

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 6/11

8:06 am-12:29 pm

1 stop5h 23m

Chicago Midway

Wed 8/27

1:00 pm-5:07 pm

1 stop3h 07m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 5/22

5:49 pm-8:21 pm

1 stop3h 32m

Chicago O'Hare Intl

Sun 5/25

7:10 am-11:18 am

1 stop3h 08m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sun 6/15

6:48 pm-7:23 pm

Nonstop1h 35m

Chicago O'Hare Intl

Sat 6/21

8:45 pm-11:28 pm

Nonstop1h 43m

$217

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 5/13

6:10 pm-6:55 pm

Nonstop1h 45m

Chicago O'Hare Intl

Tue 5/20

2:58 pm-5:29 pm

Nonstop1h 31m

$254

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

Wed 6/11

9:13 pm-9:52 am

1 stop13h 39m

Chicago Greater Rockford

Wed 8/27

6:03 pm-7:37 pm

1 stop24h 34m

$278

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

Wed 6/4

9:13 pm-9:52 am

1 stop13h 39m

$154

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 6/4

9:13 pm-10:55 am

1 stop14h 42m

$157

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 5/8

5:07 pm-12:05 am

1 stop7h 58m

$160

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 5/28

8:10 am-9:30 pm

2 stops14h 20m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 13 results
1
2

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*2 stars
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 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 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 April 25, 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 May 1, 2025.

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 46% on your trip compared to booking a flight in the evening.

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 June 9, 2024.

Travelers seeking maximum savings on their Lexington to Chicago flight should consider departing on Friday 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 May 1, 2025.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 1, 2025.
To help decide which airline to fly from Lexington to Chicago, see what other customers have to say about Delta, United Airlines and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    Delta, at $209, was found to be the cheapest airline from Lexington to Chicago.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Delta is currently priced 25% 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 $154. Users have also found prices from $186 and $194 on United Airlines and Delta, 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 (85%), SkyWest Airlines (85%), Envoy Air (85%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $1,347 for a flight from Lexington to Chicago. The cheapest flight overall is $128 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 Lexington?

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

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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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$173Average$271FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$188Average$278FlexibilityNo cancel feeOn-time69%

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