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$131+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in November or September, booked 82 days in advance, depart on a Wednesday or Friday 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 July 30, 2025.

Round-trip from

$189
(American Airlines)

One-way from

$131
(Mytrip)

Popular in

June

Cheapest in

November

Average price

$284

Good round-trip deal

$322 or less

Good one-way deal

$249 or less
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. 5% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:44 amLEX - ORD
Nonstop1h 36mAmerican Airlines
Sun 8/248:44 amORD - LEX
Nonstop1h 27mAmerican Airlines
Deal found 7/30$189
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2110:24 amLEX - MDW
1 stop3h 04mDelta
Sat 8/236:04 amMDW - LEX
1 stop5h 14mDelta
Deal found 7/28$209
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:42 pmLEX - ORD
1 stop7h 16mDelta
Tue 1/137:10 amORD - LEX
1 stop6h 19mDelta
Deal found 7/28$209
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:58 pmLEX - ORD
Nonstop1h 57mUnited Airlines
Sun 1/119:10 pmORD - LEX
Nonstop1h 31mUnited Airlines
Deal found 7/28$249
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Thu 8/147:47 pmLEX - ORD
1 stop14h 34mMultiple Airlines
Sat 8/168:12 pmORD - LEX
2 stops19h 18mMultiple Airlines
Deal found 7/30$266
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Tue 11/259:31 pmLEX - MDW
2 stops16h 50mAllegiant Air
Sun 11/304:24 pmMDW - LEX
2 stops19h 04mAllegiant Air
Deal found 7/29$902

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 July 30, 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

Thu 8/21

11:44 am-12:20 pm

Nonstop1h 36m

Chicago O'Hare Intl

Sun 8/24

8:44 am-11:11 am

Nonstop1h 27m

$189

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 8/21

10:24 am-12:28 pm

1 stop3h 04m

Chicago Midway

Sat 8/23

6:04 am-12:18 pm

1 stop5h 14m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 12/23

5:42 pm-11:58 pm

1 stop7h 16m

Chicago O'Hare Intl

Tue 1/13

7:10 am-2:29 pm

1 stop6h 19m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 12/23

1:58 pm-2:55 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 1/11

9:10 pm-11:41 pm

Nonstop1h 31m

$249

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 8/14

7:47 pm-9:21 am

1 stop14h 34m

Chicago O'Hare Intl

Sat 8/16

8:12 pm-4:30 pm

2 stops19h 18m

$266

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Tue 11/25

9:31 pm-1:21 pm

2 stops16h 50m

Chicago Midway

Sun 11/30

4:24 pm-12:28 pm

2 stops19h 04m

$902

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sun 8/17

7:47 pm-4:10 pm

2 stops21h 23m

$131

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

Thu 8/21

8:27 pm-10:13 am

1 stop14h 46m

$140

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 8/21

9:19 am-8:42 am

2 stops24h 23m

$167

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 8/30

6:41 am-5:12 pm

2 stops11h 31m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 results
1
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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 July 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 July 30, 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 40% 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 Saturday evenings 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 July 30, 2025.

The most flights from LEX to CHI are scheduled on a Tuesday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 July 30, 2025.
Peruse reviews from past customers who have flown with Delta, 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.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.2
Good
703 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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

  • 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.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is currently priced 30% 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 $153. Users have also found prices from $201 and $213 on American 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: Avianca (97%), ANA (87%), GoJet (87%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $968 for a flight from Lexington to Chicago. The cheapest flight overall is $194 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$188Average$268FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$275FlexibilityNo cancel feeOn-time69%

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