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$118+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in May 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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 3/145:39 pm
LEX
-
ORD
Nonstop1h 46m
United Airlines
Fri 3/209:20 pm
ORD
-
LEX
Nonstop1h 24m
United Airlines
Deal found 1/28$189
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Sat 2/214:59 pm
LEX
-
ORD
Nonstop1h 40m
American Airlines
Sun 2/227:04 am
ORD
-
LEX
Nonstop1h 24m
American Airlines
Deal found 1/29$191
This United Airlines deal was found by Cheapflights users on 1/27. 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 7/215:50 pm
LEX
-
ORD
Nonstop1h 33m
United Airlines
Sat 7/252:24 pm
ORD
-
LEX
Nonstop1h 31m
United Airlines
Deal found 1/27$197
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/244:27 pm
LEX
-
ORD
Nonstop1h 45m
American Airlines
Mon 4/278:51 pm
ORD
-
LEX
Nonstop1h 33m
American Airlines
Deal found 1/27$204
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
LEX
-
ORD
Nonstop1h 47m
American Airlines
Mon 4/208:51 pm
ORD
-
LEX
Nonstop1h 33m
American Airlines
Deal found 1/28$206
This Delta deal was found by Cheapflights users on 1/28. 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 4/167:30 am
LEX
-
MDW
1 stop6h 13m
Delta
Wed 4/226:00 am
MDW
-
LEX
1 stop4h 46m
Delta
Deal found 1/28$209
This Delta deal was found by Cheapflights users on 1/28. 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 4/167:30 am
LEX
-
ORD
1 stop6h 15m
Delta
Sat 4/185:10 am
ORD
-
LEX
1 stop5h 36m
Delta
Deal found 1/28$209
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1210:27 am
LEX
-
ORD
Nonstop1h 35m
American Airlines
Mon 2/167:04 am
ORD
-
LEX
Nonstop1h 24m
American Airlines
Deal found 1/28$219
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 3/147:45 am
LEX
-
MDW
1 stop5h 44m
Delta
Tue 3/1712:47 pm
MDW
-
LEX
1 stop5h 23m
Delta
Deal found 1/28$224
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 3/305:49 pm
LEX
-
ORD
1 stop3h 28m
Delta
Mon 4/69:50 am
ORD
-
LEX
1 stop6h 17m
Delta
Deal found 1/28$224
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/2010:27 am
LEX
-
ORD
Nonstop1h 35m
American Airlines
Sun 2/227:04 am
ORD
-
LEX
Nonstop1h 24m
American Airlines
Deal found 1/27$234
This Delta deal was found by Cheapflights users on 1/28. 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 2/127:26 am
LEX
-
ORD
1 stop6h 54m
Delta
Mon 2/162:05 pm
ORD
-
LEX
1 stop6h 34m
Delta
Deal found 1/28$239

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$118
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$268

Good round-trip deal

$366 or less

Good one-way deal

$320 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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 7/21

7:25 am-7:58 am

Nonstop1h 33m

Chicago O'Hare Intl

Sat 7/25

2:24 pm-4:55 pm

Nonstop1h 31m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 2/26

5:07 pm-5:47 pm

Nonstop1h 40m

Chicago O'Hare Intl

Sat 2/28

7:04 am-9:28 am

Nonstop1h 24m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 3/5

5:07 pm-5:47 pm

Nonstop1h 40m

Chicago O'Hare Intl

Tue 3/10

1:28 pm-3:51 pm

Nonstop1h 23m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 3/14

5:39 pm-6:25 pm

Nonstop1h 46m

Chicago O'Hare Intl

Fri 3/20

9:20 pm-11:44 pm

Nonstop1h 24m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 2/21

4:59 pm-5:39 pm

Nonstop1h 40m

Chicago O'Hare Intl

Sun 2/22

7:04 am-9:28 am

Nonstop1h 24m

$191

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Wed 6/3

6:00 am-6:36 am

Nonstop1h 36m

Chicago O'Hare Intl

Mon 6/8

8:53 am-11:26 am

Nonstop1h 33m

$204

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 2/20

7:26 am-12:46 pm

1 stop6h 20m

Chicago Midway

Sun 2/22

9:34 am-4:51 pm

1 stop6h 17m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/1

7:45 am-12:29 pm

1 stop5h 44m

Chicago Midway

Wed 4/8

1:10 pm-5:07 pm

1 stop2h 57m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Wed 4/1

7:45 am-12:29 pm

1 stop5h 44m

Chicago Midway

Tue 4/7

1:10 pm-5:07 pm

1 stop2h 57m

$209

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Tue 3/31

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Tue 4/7

6:00 am-11:54 am

1 stop4h 54m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January.
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 January 23, 2026.

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, 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 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 January 29, 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 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 January 24, 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 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 January 29, 2026.

The most flights from LEX to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 January 29, 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
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 18 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 33m. The time it takes to get you to your destination can typically vary by up to 4h 47m. 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: PSA Airlines (100%), United Airlines (78%), Qatar Airways (75%).

  • What are the cheapest flights from Lexington to Chicago?

    On average you can expect to pay $896 for a flight from Lexington to Chicago. The cheapest flight overall is $213 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, 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 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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Alternative routes for Lexington to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$189Average$271FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$279FlexibilityNo cancel feeOn-time71%

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