$102+ Cheap flights from Chicago (CHI) to Lexington (LEX)
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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Feb 11 — Feb 181
1 adult, Economy
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Find cheap flights from Chicago to Lexington with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Lexington
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Lexington (LEX). 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 12, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $189 (American Airlines) |
One-way from | $102 (Kiwi.com) |
Popular in | October |
Cheapest in | December |
Average price | $222 |
Good round-trip deal | $189 or less |
Good one-way deal | $138 or less |
Find flight deals from Chicago to Lexington
Cheapest flights from Chicago to LexingtonExplore the most affordable flight options available from Chicago to Lexington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.
Explore the most affordable flight options available from Chicago to Lexington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.
This American Airlines deal was found by Cheapflights users on 1/10. 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 2/137:04 am
ORD
- LEX
Nonstop1h 24m
American Airlines
Mon 2/1610:27 am
LEX
- ORD
Nonstop1h 35m
American Airlines
Deal found 1/10![American Airlines logo]()
$189
This United Airlines deal was found by Cheapflights users on 1/11. 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.
Thu 1/295:59 pm
ORD
- LEX
Nonstop1h 32m
United Airlines
Sun 2/15:32 pm
LEX
- ORD
Nonstop1h 57m
United Airlines
Deal found 1/11![United Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 1/11. 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 4/185:03 pm
ORD
- LEX
1 stop3h 39m
Delta
Mon 4/207:55 pm
LEX
- ORD
1 stop5h 02m
Delta
Deal found 1/11![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 1/10. 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.
Wed 4/12:25 pm
ORD
- LEX
Nonstop1h 37m
United Airlines
Mon 4/65:45 pm
LEX
- ORD
Nonstop1h 49m
United Airlines
Deal found 1/10![United Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 1/11. 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 2/277:04 am
ORD
- LEX
Nonstop1h 24m
American Airlines
Sun 3/18:14 am
LEX
- ORD
Nonstop1h 43m
American Airlines
Deal found 1/11![American Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 1/11. 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 3/126:25 am
MDW
- LEX
1 stop4h 29m
Delta
Sun 3/157:45 am
LEX
- MDW
1 stop5h 44m
Delta
Deal found 1/11![Delta logo]()
$224
This Delta deal was found by Cheapflights users on 1/9. 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 1/291:58 pm
ORD
- LEX
1 stop6h 43m
Delta
Thu 2/510:37 am
LEX
- ORD
1 stop3h 36m
Delta
Deal found 1/9![Delta logo]()
$224
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Tue 2/37:59 pm
ORD
- LEX
1 stop18h 38m
American Airlines
Wed 2/44:58 pm
LEX
- ORD
Nonstop1h 51m
American Airlines
Deal found 1/10![American Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 1/12. 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 3/59:34 am
MDW
- LEX
1 stop6h 17m
Delta
Sun 3/87:45 am
LEX
- MDW
1 stop5h 44m
Delta
Deal found 1/12![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 1/12. 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 3/510:35 am
ORD
- LEX
1 stop5h 16m
Delta
Tue 3/1010:30 am
LEX
- ORD
1 stop3h 47m
Delta
Deal found 1/12![Delta logo]()
$229
This American Airlines deal was found by Cheapflights users on 1/10. 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 2/137:04 am
ORD
- LEX
Nonstop1h 24m
American Airlines
Sun 2/1511:21 am
LEX
- ORD
1 stop5h 00m
American Airlines
Deal found 1/10![American Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 1/12. 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 2/81:45 pm
ORD
- LEX
Nonstop1h 29m
American Airlines
Sun 2/1510:27 am
LEX
- ORD
Nonstop1h 35m
American Airlines
Deal found 1/12![American Airlines logo]()
$233
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Lexington 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 12, 2026.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.
Fly from
Chicago
Fly to
Lexington
Route
Depart
Return
Price
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Tue 2/3
8:05 pm-10:40 pm
Nonstop1h 35m
Lexington Blue Grass
Tue 2/10
5:32 pm-6:29 pm
Nonstop1h 57m
$189
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Sat 2/14
7:04 am-9:28 am
Nonstop1h 24m
Lexington Blue Grass
Sun 2/22
8:14 am-8:57 am
Nonstop1h 43m
$189
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Sat 2/14
9:25 pm-11:49 pm
Nonstop1h 24m
Lexington Blue Grass
Sat 2/21
5:45 pm-6:31 pm
Nonstop1h 46m
$189
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Fri 1/30
8:05 pm-10:40 pm
Nonstop1h 35m
Lexington Blue Grass
Sun 2/1
5:32 pm-6:29 pm
Nonstop1h 57m
$204
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Thu 1/29
5:59 pm-8:31 pm
Nonstop1h 32m
Lexington Blue Grass
Sun 2/1
5:32 pm-6:29 pm
Nonstop1h 57m
$204
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Wed 2/4
10:35 am-4:50 pm
1 stop5h 15m
Lexington Blue Grass
Wed 2/11
5:35 pm-9:05 pm
1 stop4h 30m
$209
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Sat 4/18
10:45 am-5:08 pm
1 stop5h 23m
Lexington Blue Grass
Mon 4/20
7:55 pm-11:57 pm
1 stop5h 02m
$209
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Tue 2/3
10:35 am-4:50 pm
1 stop5h 15m
Lexington Blue Grass
Tue 2/10
10:37 am-1:13 pm
1 stop3h 36m
$209
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Wed 4/1
2:25 pm-5:02 pm
Nonstop1h 37m
Lexington Blue Grass
Mon 4/6
5:45 pm-6:34 pm
Nonstop1h 49m
$221
ChicagoLexington
ORD - LEX
ORDLEX
Chicago O'Hare Intl
Sun 2/8
8:05 pm-10:40 pm
Nonstop1h 35m
Lexington Blue Grass
Sun 2/15
7:00 am-7:44 am
Nonstop1h 44m
$222
Showing 1-10 of 39 results
Compare providers for flights from Chicago to Lexington
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 Chicago to Lexington in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Lexington flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Lexington flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Lexington flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Lexington 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 Chicago-Lexington 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 Chicago to Lexington
Have a flexible travel schedule? Discover the best time to fly to Lexington from Chicago 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 Chicago to Lexington
What is the cheapest month to book a flight from Chicago to Lexington?
Currently, June is the cheapest month in which you can book a flight from Chicago to Lexington (average of $98). Flying from Chicago to Lexington in July 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 CHI to LEX?
Find hourly flight availability from Chicago to Lexington. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 12, 2026.
When flying from Chicago to Lexington, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 18% versus a flight at noon.
What is the cheapest day to fly from Chicago to Lexington?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Lexington. Price data was last updated on January 10, 2026.
Travelers seeking maximum savings on their Chicago to Lexington flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Lexington
Explore weekly flight availability from Chicago to Lexington. 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 12, 2026.
The most flights from CHI to LEX are scheduled on a Thursday (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 Lexington
Get insights into the airlines that provide service to Lexington. 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 Lexington. Reviews last updated January 12, 2026.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Lexington have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Boarding
7.7
Comfort
7.3
Food
6.6
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Boarding
7.7
Comfort
7.3
Food
6.6
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Boarding
7.7
Comfort
7.3
Food
6.6
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Chicago to Lexington. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Lexington?
Book flights to Lexington if you plan to visit one of these locationsSomerset
Berea
Georgetown
Frankfort
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Alternative routes for Chicago to Lexington
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Chicago to Lexington
Discover the top 2 airlines that operate flights from Chicago to Lexington. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$263 | FlexibilityNo cancel fee | On-time71% |