$140+ Cheap flights from Lexington (LEX) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Oct 22 — Oct 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Lexington to Chicago 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.Cheapflights Tip: The best prices from Lexington Blue Grass to Chicago are usually found in February or December, booked 78 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Lexington to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Lexington to ChicagoExplore 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 September 22, 2026.
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 September 22, 2026.
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/236:00 am -
Nonstop1h 45m
Mon 10/264:30 pm -
Nonstop1h 40m
Deal found 9/21![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/238:03 pm -
1 stop5h 05m
Sun 10/253:45 pm -
Nonstop1h 39m
Deal found 9/18![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:29 am -
Nonstop1h 39m
Tue 10/2712:05 pm -
1 stop5h 39m
Deal found 9/19![American Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/96:00 am -
Nonstop1h 45m
Mon 10/196:50 am -
Nonstop1h 38m
Deal found 9/21![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:53 pm -
1 stop3h 37m
Tue 10/278:05 am -
1 stop5h 44m
Deal found 9/19![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Sat 10/246:58 pm -
Nonstop2h 01m
Tue 10/279:35 pm -
Nonstop1h 34m
Deal found 9/20![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 10/98:03 pm -
1 stop5h 05m
Sun 10/119:35 pm -
Nonstop1h 34m
Deal found 9/20![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 am -
Nonstop1h 45m
Sun 10/46:50 am -
Nonstop1h 38m
Deal found 9/18![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/245:30 am -
Nonstop1h 45m
Mon 11/309:30 pm -
Nonstop1h 24m
Deal found 9/17![United Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:00 am -
1 stop5h 10m
Tue 10/279:35 pm -
Nonstop1h 34m
Deal found 9/19![American Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/96:59 pm -
1 stop5h 58m
Tue 10/206:30 am -
1 stop4h 28m
Deal found 9/21![Delta logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 10/95:29 am -
Nonstop1h 39m
Sat 10/1012:05 pm -
1 stop4h 20m
Deal found 9/20![American Airlines logo]()
$339
Best flights from Lexington to ChicagoDiscover carefully curated flight deals from Lexington to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Lexington to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:10 am -
Nonstop1h 46m
Sat 11/287:40 am -
Nonstop1h 33m
Deal found 9/18![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 12/1112:45 pm -
1 stop7h 20m
Sun 12/138:04 am -
1 stop5h 43m
Deal found 9/21![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Sat 10/176:00 am -
Nonstop1h 45m
Sat 10/2410:41 am -
Nonstop1h 40m
Deal found 9/19![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/21. 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 11/1811:05 am -
Nonstop1h 47m
Mon 11/239:30 pm -
Nonstop1h 24m
Deal found 9/21![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:30 am -
Nonstop1h 45m
Mon 11/24:30 pm -
Nonstop1h 40m
Deal found 9/20![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Fri 11/135:25 am -
Nonstop1h 45m
Mon 11/169:30 pm -
Nonstop1h 24m
Deal found 9/19![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/196:05 pm -
Nonstop1h 52m
Mon 10/267:40 am -
Nonstop1h 33m
Deal found 9/21![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Thu 10/228:50 am -
Nonstop1h 45m
Sat 10/2410:41 am -
Nonstop1h 40m
Deal found 9/22![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:56 pm -
Nonstop1h 44m
Mon 10/126:50 am -
Nonstop1h 38m
Deal found 9/20![United Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 am -
Nonstop1h 45m
Sun 10/46:50 am -
Nonstop1h 38m
Deal found 9/18![United Airlines logo]()
$329
Last-minute flights from Lexington to ChicagoDiscover last-minute flight deals from Lexington to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Lexington to Chicago. Data last updated September 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/111:43 am -
1 stop5h 17m
Sun 10/45:18 am -
1 stop4h 14m
Deal found 9/17![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:50 am -
Nonstop1h 45m
Sun 10/46:50 am -
Nonstop1h 38m
Deal found 9/18![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/96:00 am -
Nonstop1h 45m
Mon 10/196:50 am -
Nonstop1h 38m
Deal found 9/21![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 10/98:03 pm -
1 stop5h 05m
Sun 10/119:35 pm -
Nonstop1h 34m
Deal found 9/20![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/96:59 pm -
1 stop5h 58m
Tue 10/206:30 am -
1 stop4h 28m
Deal found 9/21![Delta logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 10/95:29 am -
Nonstop1h 39m
Sat 10/1012:05 pm -
1 stop4h 20m
Deal found 9/20![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:29 am -
Nonstop1h 39m
Tue 10/2712:05 pm -
1 stop5h 39m
Deal found 9/19![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:53 pm -
1 stop3h 37m
Tue 10/278:05 am -
1 stop5h 44m
Deal found 9/19![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Fri 10/236:00 am -
Nonstop1h 45m
Mon 10/264:30 pm -
Nonstop1h 40m
Deal found 9/21![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/238:03 pm -
1 stop5h 05m
Sun 10/253:45 pm -
Nonstop1h 39m
Deal found 9/18![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:00 am -
1 stop5h 10m
Tue 10/279:35 pm -
Nonstop1h 34m
Deal found 9/19![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Sat 10/246:58 pm -
Nonstop2h 01m
Tue 10/279:35 pm -
Nonstop1h 34m
Deal found 9/20![American Airlines logo]()
$322
One-way flights from Lexington to ChicagoSearch for one-way flight options from Lexington to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Lexington to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:11 pm -
1 stop19h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:10 pm -
1 stop18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Sun 10/188:59 pm -
1 stop19h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:53 pm -
1 stop19h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:20 pm -
1 stop18h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$179
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (United Airlines) |
One-way from | $140 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $329 |
Good round-trip deal | $386 or less |
Good one-way deal | $329 or less |
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 7,457,451 searches. Data last updated September 22, 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
Cheapest round-trip
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Wed 12/23
5:50 pm-6:43 pm
Nonstop1h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Sun 11/22
5:25 am-6:10 am
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 10/30
6:15 pm-7:05 pm
Nonstop1h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Sat 12/19
10:45 am-11:50 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Tue 10/20
6:05 pm-6:57 pm
Nonstop1h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 10/23
8:50 am-9:35 am
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
Quickest round-trip
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Mon 11/16
9:00 am-9:40 am
Nonstop1h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 10/16
1:56 pm-2:40 pm
Nonstop1h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Mon 12/21
1:55 pm-2:55 pm
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Sun 10/18
8:50 am-9:35 am
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
Showing 1-10 of 21 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
LEX-CHI
LEX-ORD
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
LEX-CHI
LEX-ORD
What is the cheapest month to book a flight from Lexington to Chicago?
Currently, February is the cheapest month in which you can book a flight from Lexington to Chicago (average of $238). Flying from Lexington to Chicago in July is currently the most expensive (average of $344). 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 September 22, 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 34% on your trip compared to booking a flight at noon.
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 September 22, 2026.
The most flights from LEX to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Tuesday, 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?
Airfare is typical for this route at the moment.
Lexington to Chicago flights typically cost between $247 and $438 in October.The cheapest round-trip price found within the last 5 days was $299 on United Airlines (Oct 15-Oct 19).
How far ahead should I book a flight from Lexington to Chicago?
To ensure you get the cheapest price possible for a flight from Lexington to Chicago, you should look to book at least 67 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 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 September 19, 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.
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 September 22, 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.
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Lexington
Popular flights
Alternative routes for Lexington to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Lexington to Chicago by cabin class
Find flights from Lexington to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Lexington and Chicago flights
Browse other Lexington and Chicago flight options. Last updated on September 22, 2026.
Other flights from Lexington
Browse through other flights departing from Lexington. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$300 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$303 | FlexibilityNo cancel fee | On-time71% |