$139+ Cheap flights from Lexington (LEX) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — CHI
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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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 September, booked 70 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Lexington to Chicago
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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 August 6, 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 August 6, 2026.
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/46:34 am -
Nonstop1h 56m
Sun 9/69:15 pm -
Nonstop1h 31m
Deal found 8/5![American Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/276:30 am -
Nonstop1h 56m
Sun 8/309:15 pm -
Nonstop1h 31m
Deal found 8/5![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 9/56:34 am -
Nonstop1h 56m
Mon 9/79:15 pm -
Nonstop1h 31m
Deal found 8/4![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 8/226:30 am -
Nonstop1h 56m
Wed 8/269:15 pm -
Nonstop1h 31m
Deal found 8/4![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 8/4. 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.
Thu 9/176:00 pm -
1 stop3h 30m
Mon 9/216:40 am -
1 stop4h 04m
Deal found 8/4![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/117:00 am -
Nonstop1h 45m
Mon 9/149:30 pm -
Nonstop1h 35m
Deal found 8/5![United Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/4. 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 8/285:00 pm -
1 stop7h 52m
Sun 8/306:49 am -
1 stop5h 06m
Deal found 8/4![American Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 8/4. 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 8/224:30 pm -
1 stop7h 06m
Wed 8/266:05 am -
1 stop5h 06m
Deal found 8/4![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
1 stop6h 36m
Tue 9/86:05 am -
1 stop4h 39m
Deal found 8/4![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/5. 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 9/197:00 am -
1 stop4h 36m
Sat 9/264:30 pm -
1 stop5h 12m
Deal found 8/5![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/1110:39 am -
1 stop6h 38m
Sat 9/126:05 am -
1 stop5h 13m
Deal found 8/3![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/1110:39 am -
1 stop6h 38m
Mon 9/146:05 am -
1 stop4h 39m
Deal found 8/3![Delta 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 August 6, 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 August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 9/37:00 am -
Nonstop1h 45m
Sun 9/139:30 pm -
Nonstop1h 35m
Deal found 8/4![United Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/176:01 pm -
Nonstop1h 58m
Sun 9/209:15 pm -
Nonstop1h 31m
Deal found 8/5![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/1. 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 9/510:54 am -
1 stop5h 50m
Tue 9/86:05 am -
1 stop4h 39m
Deal found 8/1![Delta logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 11/58:48 am -
1 stop24h 50m
Mon 11/910:38 am -
1 stop22h 55m
Deal found 8/3![Allegiant Air logo]()
$390
This United Airlines deal was found by Cheapflights users on 8/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm -
Nonstop1h 50m
Mon 9/79:20 pm -
Nonstop1h 35m
Deal found 8/2![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/4. 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 11/135:59 pm -
1 stop5h 57m
Sat 11/1411:28 am -
1 stop4h 39m
Deal found 8/4![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/1111:43 am -
1 stop6h 55m
Sun 9/135:18 am -
1 stop4h 14m
Deal found 8/5![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/3. 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 9/55:00 pm -
1 stop6h 36m
Sun 9/66:05 am -
1 stop5h 06m
Deal found 8/3![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/1. 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 11/2010:30 am -
1 stop6h 54m
Sat 11/282:44 pm -
1 stop5h 34m
Deal found 8/1![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/4. 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 9/116:00 pm -
1 stop3h 30m
Mon 9/145:30 am -
1 stop5h 14m
Deal found 8/4![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/3. 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 9/510:52 am -
1 stop3h 58m
Tue 9/811:17 am -
1 stop5h 03m
Deal found 8/3![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/4. 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.
Thu 9/37:35 am -
1 stop6h 33m
Sun 9/135:30 am -
1 stop4h 20m
Deal found 8/4![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 10/237:59 pm -
1 stop4h 53m
Tue 10/275:27 am -
1 stop5h 31m
Deal found 8/3![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/5. 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 8/224:30 pm -
1 stop7h 06m
Wed 8/266:05 am -
1 stop5h 06m
Deal found 8/5![Delta logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:41 am -
1 stop6h 55m
Thu 8/2010:44 am -
1 stop29h 48m
Deal found 8/2![Allegiant Air logo]()
$634
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/1110:39 am -
1 stop6h 38m
Mon 9/146:05 am -
1 stop4h 39m
Deal found 8/3![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/2. 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.
Sat 10/37:35 am -
1 stop6h 04m
Thu 10/85:15 pm -
1 stop5h 43m
Deal found 8/2![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 8/2. 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 9/107:00 am -
1 stop4h 36m
Mon 9/146:05 am -
1 stop4h 39m
Deal found 8/2![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 8/5. 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 9/196:00 am -
1 stop5h 36m
Sun 9/206:05 am -
1 stop4h 39m
Deal found 8/5![Delta logo]()
$439
Last-minute flights from Lexington to ChicagoDiscover last-minute flight deals from Lexington to Chicago. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Lexington to Chicago. Data last updated August 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 8/226:30 am -
Nonstop1h 56m
Wed 8/269:15 pm -
Nonstop1h 31m
Deal found 8/4![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 8/4. 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 8/224:30 pm -
1 stop7h 06m
Wed 8/266:05 am -
1 stop5h 06m
Deal found 8/4![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/276:30 am -
Nonstop1h 56m
Sun 8/309:15 pm -
Nonstop1h 31m
Deal found 8/5![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 8/4. 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 8/285:00 pm -
1 stop7h 52m
Sun 8/306:49 am -
1 stop5h 06m
Deal found 8/4![American Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/46:34 am -
Nonstop1h 56m
Sun 9/69:15 pm -
Nonstop1h 31m
Deal found 8/5![American Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 9/56:34 am -
Nonstop1h 56m
Mon 9/79:15 pm -
Nonstop1h 31m
Deal found 8/4![American Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
1 stop6h 36m
Tue 9/86:05 am -
1 stop4h 39m
Deal found 8/4![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 9/117:00 am -
Nonstop1h 45m
Mon 9/149:30 pm -
Nonstop1h 35m
Deal found 8/5![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/1110:39 am -
1 stop6h 38m
Sat 9/126:05 am -
1 stop5h 13m
Deal found 8/3![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/1110:39 am -
1 stop6h 38m
Mon 9/146:05 am -
1 stop4h 39m
Deal found 8/3![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/4. 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.
Thu 9/176:00 pm -
1 stop3h 30m
Sun 9/205:30 am -
1 stop5h 14m
Deal found 8/4![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 8/5. 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 9/197:00 am -
1 stop4h 36m
Sat 9/264:30 pm -
1 stop5h 12m
Deal found 8/5![Delta logo]()
$308
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 August 6, 2026.
Search for one-way flight options from Lexington to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 11/17:22 pm -
1 stop21h 02m
Deal found 8/4![Multiple Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 8/296:30 am -
Nonstop1h 56m
Deal found 8/4![American Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/246:40 pm -
1 stop21h 05m
Deal found 8/4![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/19:11 pm -
1 stop18h 34m
Deal found 8/5![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 11/87:24 pm -
2 stops27h 10m
Deal found 8/5![Multiple Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Fri 8/146:30 am -
Nonstop1h 56m
Deal found 8/5![American Airlines logo]()
$153
This Delta deal was found by Cheapflights users on 8/4. 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 9/510:52 am -
1 stop6h 25m
Deal found 8/4![Delta logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 10/215:36 pm -
1 stop16h 42m
Deal found 8/3![Allegiant Air logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/246:40 pm -
2 stops24h 11m
Deal found 8/4![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/19:11 pm -
2 stops21h 40m
Deal found 8/5![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 10/56:59 pm -
1 stop18h 53m
Deal found 8/3![Allegiant Air logo]()
$205
This Delta deal was found by Cheapflights users on 8/4. 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 9/235:57 pm -
1 stop5h 47m
Deal found 8/4![Delta logo]()
$259
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $215 (American Airlines) |
One-way from | $139 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $284 |
Good round-trip deal | $370 or less |
Good one-way deal | $324 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 2,558,603 searches. Data last updated August 6, 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
Quickest round-trip
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Thu 9/3
7:00 am-7:45 am
Nonstop1h 45m
Chicago O'Hare Intl
Sun 9/13
9:30 pm-12:05 am
Nonstop1h 35m
$259
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Thu 9/17
6:01 pm-6:59 pm
Nonstop1h 58m
Chicago O'Hare Intl
Sun 9/20
9:15 pm-11:46 pm
Nonstop1h 31m
$259
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Sat 9/5
7:15 pm-8:05 pm
Nonstop1h 50m
Chicago O'Hare Intl
Mon 9/7
9:20 pm-11:55 pm
Nonstop1h 35m
$259
LexingtonChicago
LEX Lexington Blue Grass - MDW Chicago Midway
LEXMDW
Lexington Blue Grass
Sat 9/5
10:54 am-3:44 pm
1 stop5h 50m
Chicago Midway
Tue 9/8
6:05 am-11:44 am
1 stop4h 39m
$279
LexingtonChicago
LEX Lexington Blue Grass - MDW Chicago Midway
LEXMDW
Lexington Blue Grass
Fri 11/13
5:59 pm-10:56 pm
1 stop5h 57m
Chicago Midway
Sat 11/14
11:28 am-5:07 pm
1 stop4h 39m
$279
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 9/11
11:43 am-5:38 pm
1 stop6h 55m
Chicago O'Hare Intl
Sun 9/13
5:18 am-10:32 am
1 stop4h 14m
$279
LexingtonChicago
LEX Lexington Blue Grass - MDW Chicago Midway
LEXMDW
Lexington Blue Grass
Sat 9/5
5:00 pm-10:36 pm
1 stop6h 36m
Chicago Midway
Sun 9/6
6:05 am-12:11 pm
1 stop5h 06m
$279
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 11/20
10:30 am-4:24 pm
1 stop6h 54m
Chicago O'Hare Intl
Sat 11/28
2:44 pm-9:18 pm
1 stop5h 34m
$279
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Fri 9/11
6:00 pm-8:30 pm
1 stop3h 30m
Chicago O'Hare Intl
Mon 9/14
5:30 am-11:44 am
1 stop5h 14m
$279
LexingtonChicago
LEX Lexington Blue Grass - ORD Chicago O'Hare Intl
LEXORD
Lexington Blue Grass
Sat 9/5
10:52 am-1:50 pm
1 stop3h 58m
Chicago O'Hare Intl
Tue 9/8
11:17 am-5:20 pm
1 stop5h 03m
$279
Showing 1-10 of 40 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 August.
| 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
LEX-MDW
LEX-RFD
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
LEX-MDW
LEX-RFD
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 May is currently the most expensive (average of $342). 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 August 6, 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 August 6, 2026.
The most flights from LEX to CHI are scheduled on a Wednesday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Lexington to Chicago?
Airfare is below average for this route at the moment.
Lexington to Chicago flights typically cost between $252 and $453 in September.The cheapest round-trip price found within the last 5 days was $215 on American Airlines (Sep 4-Sep 6).
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 29 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 August 1, 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 August 6, 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
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - 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
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Other flights to Chicago
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Lexington and Chicago flights
Browse other Lexington and Chicago flight options. Last updated on August 6, 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 August 6, 2026.
Popular flight searches
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Top 2 airlines flying from Lexington to Chicago
Discover the top 2 airlines that operate flights from Lexington to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$281 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$282 | FlexibilityNo cancel fee | On-time71% |