$127+ Cheap flights from Chicago (CHI) to Lexington (LEX)
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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Dec 7 — Dec 141
Round-trip
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
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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 November 7, 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 November 7, 2026.
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/268:15 am -
Nonstop1h 35m
Mon 11/305:15 am -
Nonstop1h 44m
Deal found 11/2![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/179:28 pm -
Nonstop1h 31m
Sun 12/205:50 pm -
Nonstop1h 53m
Deal found 11/3![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/199:10 pm -
Nonstop1h 36m
Sun 1/1710:33 am -
1 stop6h 09m
Deal found 11/3![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/36:10 am -
1 stop8h 55m
Sun 12/65:25 pm -
2 stops29h 04m
Deal found 11/4![Multiple Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 11/3. 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 11/264:13 pm -
1 stop5h 36m
Mon 11/3012:50 pm -
1 stop4h 28m
Deal found 11/3![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/245:56 pm -
Nonstop1h 42m
Sat 12/268:30 am -
Nonstop1h 59m
Deal found 11/5![United Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 11/7. 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 11/217:40 am -
Nonstop1h 35m
Sun 11/295:25 am -
Nonstop1h 45m
Deal found 11/7![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 11/6. 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 12/211:28 am -
1 stop6h 42m
Sat 12/510:40 am -
1 stop3h 21m
Deal found 11/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/5. 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 12/2410:30 am -
1 stop5h 39m
Sat 12/265:31 pm -
1 stop3h 57m
Deal found 11/5![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/3. 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 11/181:30 pm -
1 stop4h 35m
Mon 11/2310:33 am -
1 stop4h 26m
Deal found 11/3![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/6. 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 11/209:30 pm -
Nonstop1h 24m
Sun 11/229:00 am -
Nonstop1h 40m
Deal found 11/6![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. 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 11/186:00 am -
1 stop4h 49m
Sun 11/225:59 pm -
1 stop5h 55m
Deal found 11/3![Delta logo]()
$369
Best flights from Chicago to LexingtonDiscover carefully curated flight deals from Chicago to Lexington that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 7, 2026.
Discover carefully curated flight deals from Chicago to Lexington that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 7, 2026.
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/301:59 pm -
Nonstop1h 39m
Sat 1/210:45 am -
Nonstop2h 05m
Deal found 11/5![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 11/3. 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 11/264:13 pm -
1 stop5h 36m
Mon 11/3012:50 pm -
1 stop4h 28m
Deal found 11/3![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 11/2. 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 11/267:05 am -
1 stop6h 00m
Mon 11/303:38 pm -
1 stop6h 11m
Deal found 11/2![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 11/7. 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 12/211:28 am -
1 stop6h 42m
Sat 12/510:40 am -
1 stop3h 21m
Deal found 11/7![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/109:30 pm -
Nonstop1h 26m
Sun 12/137:00 am -
Nonstop1h 51m
Deal found 11/6![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 11/5. 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 12/2410:30 am -
1 stop5h 39m
Sat 12/265:31 pm -
1 stop3h 57m
Deal found 11/5![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/215:56 pm -
Nonstop1h 42m
Sat 1/28:30 am -
Nonstop1h 59m
Deal found 11/6![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 11/5. 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 12/185:30 am -
1 stop5h 17m
Sat 12/265:31 pm -
1 stop3h 57m
Deal found 11/5![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/3. 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 11/186:00 am -
1 stop4h 49m
Sun 11/225:59 pm -
1 stop5h 55m
Deal found 11/3![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 11/4. 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 11/115:30 am -
1 stop5h 19m
Thu 3/47:30 am -
1 stop6h 14m
Deal found 11/4![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 11/7. 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 11/1111:27 am -
1 stop4h 40m
Thu 3/47:30 am -
1 stop6h 31m
Deal found 11/7![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 11/3. 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 12/313:30 pm -
1 stop6h 20m
Fri 1/16:10 am -
1 stop3h 39m
Deal found 11/3![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 11/6. 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 12/216:00 am -
1 stop4h 38m
Sat 1/26:10 am -
1 stop3h 39m
Deal found 11/6![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 11/6. 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 12/102:41 pm -
1 stop5h 40m
Fri 12/115:59 pm -
1 stop17h 50m
Deal found 11/6![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 11/5. 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 11/1411:27 am -
1 stop4h 27m
Sun 11/157:35 am -
1 stop6h 16m
Deal found 11/5![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 11/3. 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 12/56:20 am -
2 stops9h 59m
Mon 12/77:59 pm -
1 stop4h 57m
Deal found 11/3![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 11/6. 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 11/119:30 am -
2 stops8h 33m
Sun 1/176:00 am -
1 stop5h 00m
Deal found 11/6![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 11/7. 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 11/125:13 pm -
1 stop5h 45m
Sun 11/157:35 am -
1 stop6h 16m
Deal found 11/7![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 11/5. 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 12/305:05 pm -
1 stop4h 09m
Sat 1/26:10 am -
1 stop3h 39m
Deal found 11/5![Delta logo]()
$558
Last-minute flights from Chicago to LexingtonDiscover last-minute flight deals from Chicago to Lexington. Data last updated November 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Lexington. Data last updated November 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/3. 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 11/181:30 pm -
1 stop4h 35m
Mon 11/2310:33 am -
1 stop4h 26m
Deal found 11/3![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 11/3. 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 11/186:00 am -
1 stop4h 49m
Sun 11/225:59 pm -
1 stop5h 55m
Deal found 11/3![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/6. 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 11/209:30 pm -
Nonstop1h 24m
Sun 11/229:00 am -
Nonstop1h 40m
Deal found 11/6![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/7. 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 11/217:40 am -
Nonstop1h 35m
Sun 11/295:25 am -
Nonstop1h 45m
Deal found 11/7![United Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/268:15 am -
Nonstop1h 35m
Mon 11/305:15 am -
Nonstop1h 44m
Deal found 11/2![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 11/3. 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 11/264:13 pm -
1 stop5h 36m
Mon 11/3012:50 pm -
1 stop4h 28m
Deal found 11/3![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 11/6. 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 12/211:28 am -
1 stop6h 42m
Sat 12/510:40 am -
1 stop3h 21m
Deal found 11/6![Delta logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/36:10 am -
1 stop8h 55m
Sun 12/65:25 pm -
2 stops29h 04m
Deal found 11/4![Multiple Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/179:28 pm -
Nonstop1h 31m
Sun 12/205:50 pm -
Nonstop1h 53m
Deal found 11/3![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/199:10 pm -
Nonstop1h 36m
Sun 1/1710:33 am -
1 stop6h 09m
Deal found 11/3![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/245:56 pm -
Nonstop1h 42m
Sat 12/268:30 am -
Nonstop1h 59m
Deal found 11/5![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 11/5. 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 12/2410:30 am -
1 stop5h 39m
Sat 12/265:31 pm -
1 stop3h 57m
Deal found 11/5![Delta logo]()
$349
One-way flights from Chicago to LexingtonSearch for one-way flight options from Chicago to Lexington. Find affordable one-way fares based on user searches. Data last updated November 7, 2026.
Search for one-way flight options from Chicago to Lexington. Find affordable one-way fares based on user searches. Data last updated November 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 12/98:30 am -
2 stops30h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 12/910:40 am -
2 stops28h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/84:00 pm -
3 stops47h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$150
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/249:15 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Mon 12/148:30 am -
2 stops25h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/106:10 pm -
1 stop23h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Allegiant Air logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/185:58 am -
2 stops31h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 11/133:16 pm -
2 stops39h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Allegiant Air logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/106:07 am -
1 stop8h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/181:11 pm -
2 stops24h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 11/4. 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 12/118:40 pm -
1 stop22h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/207:45 am -
3 stops30h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$241
Find 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 November 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $316 (American Airlines) |
One-way from | $127 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $364 |
Good round-trip deal | $386 or less |
Good one-way deal | $300 or less |
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 7,457,451 searches. Data last updated November 7, 2026.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.
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Cheapest round-trip
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Wed 12/9
10:40 am-4:05 pm
2 stops28h 25m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Sun 12/20
5:21 am-12:42 pm
1 stop6h 21m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Thu 12/10
6:10 pm-6:40 pm
1 stop23h 30m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Thu 12/10
6:07 am-4:05 pm
1 stop8h 58m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$206
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Sun 12/20
4:53 pm-6:34 pm
1 stop24h 41m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Thu 12/10
2:35 pm-5:15 pm
Nonstop1h 40m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Quickest round-trip
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Tue 12/8
9:30 pm-11:56 pm
Nonstop1h 26m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Sun 11/29
7:40 am-10:13 am
Nonstop1h 33m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Mon 12/14
6:55 am-9:30 am
Nonstop1h 35m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Thu 12/3
11:28 am-7:12 pm
1 stop6h 44m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
Showing 1-10 of 38 resultsSorted by cheapest first
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Lexington flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Lexington flight deals on Cheapflights vs. FlightHub >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 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 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.
CHI-LEX
ORD-LEX
MDW-LEX
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
CHI-LEX
ORD-LEX
MDW-LEX
What is the cheapest month to book a flight from Chicago to Lexington?
Currently, August is the cheapest month in which you can book a flight from Chicago to Lexington (average of $319). Flying from Chicago to Lexington in June is currently the most expensive (average of $478). 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 November 7, 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 morning, which can drop the price by up to 23% versus a flight in the afternoon.
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 November 7, 2026.
The most flights from CHI to LEX are scheduled on a Friday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Chicago to Lexington?
Airfare is typical for this route at the moment.
Chicago to Lexington flights typically cost between $279 and $409 in December.The cheapest round-trip price found within the last 5 days was $319 on United Airlines (Dec 17-Dec 20).
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 October 31, 2026.
Travelers seeking maximum savings on their Chicago to Lexington flight should consider departing on Wednesday evenings 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.
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 November 7, 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.
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.3
Comfort
7.3
Food
6.7
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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
Richmond
Danville
Frankfort
Georgetown
Berea
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Complete your trip
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Other flights to Lexington
Explore flights to Lexington departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 7, 2026.
Chicago and Lexington flights
Browse other Chicago and Lexington flight options. Last updated on November 7, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on November 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated November 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$340 | FlexibilityNo cancel fee | On-time71% |