$133+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — LEX
Oct 8 — Oct 151
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
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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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Fri 11/63:49 pm -
Nonstop1h 35m
Sun 11/811:26 am -
Nonstop1h 48m
Deal found 9/3![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:15 pm -
Nonstop1h 31m
Mon 9/2811:13 am -
Nonstop1h 46m
Deal found 9/5![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:35 pm -
Nonstop1h 34m
Fri 10/236:21 am -
1 stop5h 44m
Deal found 9/4![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Sun 9/208:10 am -
Nonstop1h 32m
Sat 9/266:01 pm -
Nonstop1h 58m
Deal found 9/3![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 9/248:10 am -
Nonstop1h 32m
Mon 9/2811:13 am -
Nonstop1h 46m
Deal found 9/3![American Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 9/3. 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.
Sun 12/66:00 am -
1 stop4h 48m
Sat 1/97:30 am -
1 stop6h 03m
Deal found 9/3![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:30 pm -
Nonstop1h 35m
Wed 9/235:57 pm -
Nonstop1h 52m
Deal found 9/4![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/7. 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 12/249:30 am -
1 stop6h 39m
Thu 12/3110:25 am -
1 stop5h 16m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/7. 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 12/239:30 am -
1 stop6h 41m
Sun 1/36:00 am -
1 stop3h 50m
Deal found 9/7![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 9/196:05 am -
1 stop5h 11m
Wed 9/235:57 pm -
1 stop5h 47m
Deal found 9/4![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/3. 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.
Mon 9/146:05 am -
1 stop4h 39m
Mon 9/216:00 am -
1 stop4h 49m
Deal found 9/3![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/51:00 pm -
1 stop5h 42m
Mon 10/1210:28 am -
1 stop3h 19m
Deal found 9/7![Delta logo]()
$434
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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:35 pm -
Nonstop1h 34m
Tue 10/206:58 pm -
Nonstop2h 01m
Deal found 9/7![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/3. 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.
Sun 12/66:00 am -
1 stop4h 48m
Sat 1/97:30 am -
1 stop6h 03m
Deal found 9/3![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Wed 10/76:50 am -
Nonstop1h 38m
Sun 10/116:00 am -
Nonstop1h 45m
Deal found 9/3![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:49 pm -
Nonstop1h 35m
Sun 11/811:26 am -
Nonstop1h 48m
Deal found 9/7![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/7. 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 12/249:30 am -
1 stop6h 39m
Thu 12/3110:25 am -
1 stop5h 16m
Deal found 9/7![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Fri 10/309:30 pm -
Nonstop1h 24m
Mon 11/25:30 am -
Nonstop1h 45m
Deal found 9/3![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 3/56:00 am -
1 stop5h 37m
Sun 3/77:30 am -
1 stop6h 03m
Deal found 9/7![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:15 pm -
Nonstop1h 31m
Sun 10/45:23 am -
Nonstop1h 47m
Deal found 9/7![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 1/306:00 am -
1 stop5h 37m
Fri 4/307:30 am -
1 stop6h 03m
Deal found 9/4![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:35 pm -
Nonstop1h 34m
Sat 10/105:29 am -
Nonstop1h 39m
Deal found 9/4![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/5. 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 9/266:05 am -
1 stop5h 11m
Mon 9/287:35 am -
1 stop6h 04m
Deal found 9/5![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:06 am -
Nonstop1h 38m
Sun 10/255:29 am -
Nonstop1h 39m
Deal found 9/5![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 12/259:30 am -
1 stop6h 39m
Fri 1/16:00 am -
1 stop3h 50m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/7. 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 10/151:55 pm -
1 stop6h 11m
Sat 10/175:59 pm -
1 stop6h 58m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/7. 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 10/2211:19 am -
1 stop4h 54m
Tue 10/2710:28 am -
1 stop3h 31m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/6. 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 10/296:08 pm -
1 stop4h 51m
Sun 11/17:59 pm -
1 stop4h 58m
Deal found 9/6![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/3. 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 10/75:27 am -
1 stop5h 31m
Sun 10/117:45 am -
1 stop3h 44m
Deal found 9/3![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/7. 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 10/2211:19 am -
1 stop4h 54m
Sat 10/243:34 pm -
1 stop6h 04m
Deal found 9/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/6. 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.
Sat 9/266:05 am -
1 stop5h 11m
Sun 9/277:35 am -
1 stop6h 04m
Deal found 9/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 9/196:05 am -
1 stop5h 11m
Wed 9/235:57 pm -
1 stop5h 47m
Deal found 9/4![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/7. 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 12/249:30 am -
1 stop6h 39m
Fri 1/16:00 am -
2 stops12h 24m
Deal found 9/7![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 9/6. 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.
Sat 10/36:05 am -
1 stop5h 11m
Mon 10/510:08 am -
1 stop7h 03m
Deal found 9/6![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 9/3. 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.
Sun 11/86:04 am -
1 stop4h 54m
Wed 11/117:35 am -
1 stop6h 16m
Deal found 9/3![Delta logo]()
$537
Last-minute flights from Chicago to LexingtonDiscover last-minute flight deals from Chicago to Lexington. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Lexington. Data last updated September 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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.
Mon 9/146:05 am -
1 stop4h 39m
Mon 9/216:00 am -
1 stop4h 49m
Deal found 9/3![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 9/4. 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 9/166:05 am -
1 stop4h 39m
Mon 9/216:00 am -
1 stop4h 49m
Deal found 9/4![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 9/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:30 pm -
Nonstop1h 35m
Wed 9/235:57 pm -
Nonstop1h 52m
Deal found 9/4![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 9/196:05 am -
1 stop5h 11m
Wed 9/235:57 pm -
1 stop5h 47m
Deal found 9/4![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Sun 9/208:10 am -
Nonstop1h 32m
Sat 9/266:01 pm -
Nonstop1h 58m
Deal found 9/3![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 9/248:10 am -
Nonstop1h 32m
Mon 9/2811:13 am -
Nonstop1h 46m
Deal found 9/3![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 9/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:15 pm -
Nonstop1h 31m
Mon 9/2811:13 am -
Nonstop1h 46m
Deal found 9/5![American Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 9/5. 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 9/266:05 am -
1 stop5h 11m
Mon 9/287:35 am -
1 stop6h 04m
Deal found 9/5![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/19:15 pm -
Nonstop1h 31m
Sun 10/48:13 pm -
1 stop4h 46m
Deal found 9/3![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/51:00 pm -
1 stop5h 42m
Mon 10/1210:28 am -
1 stop3h 19m
Deal found 9/7![Delta logo]()
$434
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:35 pm -
Nonstop1h 34m
Fri 10/236:21 am -
1 stop5h 44m
Deal found 9/4![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:35 pm -
Nonstop1h 34m
Tue 11/35:14 am -
Nonstop1h 45m
Deal found 9/4![American Airlines logo]()
$279
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 September 8, 2026.
Search for one-way flight options from Chicago to Lexington. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 12/35:00 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 11/58:00 am -
1 stop8h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 10/317:15 am -
2 stops35h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 11/47:15 am -
2 stops33h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 12/28:10 am -
2 stops30h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Wed 10/286:16 am -
2 stops36h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/256:40 pm -
2 stops38h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/196:25 am -
2 stops34h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/151:12 pm -
3 stops45h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 11/228:42 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 9/6. 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 10/156:04 am -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 9/5. 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 10/165:31 pm -
1 stop24h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$289
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (American Airlines) |
One-way from | $133 (Kiwi.com) |
Popular in | July |
Cheapest in | August |
Average price | $329 |
Good round-trip deal | $294 or less |
Good one-way deal | $364 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 September 8, 2026.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Sat 9/19
6:25 am-5:50 pm
2 stops34h 25m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$230
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Thu 10/15
1:12 pm-11:22 am
3 stops45h 10m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$257
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Wed 12/2
5:55 pm-8:35 pm
Nonstop1h 40m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$259
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Sun 11/22
8:42 pm-8:48 am
1 stop11h 06m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$263
ChicagoLexington
ORD Chicago O'Hare Intl - LEX Lexington Blue Grass
ORDLEX
Chicago O'Hare Intl
Tue 12/1
2:44 pm-9:21 pm
1 stop5h 37m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$269
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Wed 10/28
6:04 am-11:58 am
1 stop4h 54m
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 12/1
9:30 pm-11:56 pm
Nonstop1h 26m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Thu 10/15
6:04 am-11:58 am
1 stop4h 54m
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 10/4
5:50 pm-8:28 pm
Nonstop1h 38m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Tue 10/6
10:59 am-5:14 pm
1 stop5h 15m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
Showing 1-10 of 41 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 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 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, December is the cheapest month in which you can book a flight from Chicago to Lexington (average of $265). 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 September 8, 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 28% versus a flight in the afternoon.
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 September 5, 2026.
Travelers seeking maximum savings on their Chicago to Lexington flight should consider departing on Saturday evenings when fares are most often at their lowest. Wednesday at noon 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 September 8, 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.
Boarding
7.7
Crew
8.1
Food
6.6
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Crew
8.1
Food
6.6
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Crew
8.1
Food
6.6
Entertainment
7.1
Overall
7.4
Comfort
7.3
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
Berea
Frankfort
Georgetown
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Other flights to Lexington
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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 September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$326 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$424 | FlexibilityNo cancel fee | On-time69% |