$156+ Cheap flights from Chicago (CHI) to Harlingen (HRL)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HRL
Nov 3 — Nov 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Harlingen 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 HarlingenExplore the most affordable flight options available from Chicago to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
Explore the most affordable flight options available from Chicago to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:34 am -
1 stop5h 27m
Tue 11/241:59 pm -
1 stop7h 41m
Deal found 9/29![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:40 am -
1 stop5h 30m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 9/29![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:10 pm -
2 stops6h 40m
Wed 12/911:35 am -
2 stops6h 10m
Deal found 10/2![Southwest logo]()
$321
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:50 am -
1 stop6h 35m
Fri 12/112:00 pm -
1 stop5h 55m
Deal found 9/29![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:20 am -
1 stop7h 00m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 10/1![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:52 pm -
1 stop7h 07m
Wed 11/182:26 pm -
1 stop5h 34m
Deal found 10/1![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Wed 12/26:00 am -
1 stop7h 54m
Mon 12/76:41 pm -
1 stop5h 18m
Deal found 9/30![American Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
1 stop7h 51m
Thu 11/55:05 am -
1 stop5h 06m
Deal found 9/30![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:45 am -
1 stop4h 35m
Thu 11/54:45 pm -
1 stop8h 25m
Deal found 9/30![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:55 pm -
2 stops7h 00m
Sun 11/15:50 am -
2 stops6h 10m
Deal found 10/2![Southwest logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/29. 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 11/246:05 am -
1 stop8h 15m
Wed 12/26:41 pm -
1 stop5h 18m
Deal found 9/29![American Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:45 am -
1 stop4h 35m
Sun 11/15:50 am -
1 stop4h 30m
Deal found 10/2![Southwest logo]()
$360
Best flights from Chicago to HarlingenDiscover carefully curated flight deals from Chicago to Harlingen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
Discover carefully curated flight deals from Chicago to Harlingen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:40 am -
1 stop5h 30m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 9/29![Southwest logo]()
$311
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:50 am -
1 stop6h 35m
Fri 12/112:00 pm -
1 stop5h 55m
Deal found 9/29![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:20 am -
1 stop7h 00m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 10/1![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
1 stop7h 51m
Thu 11/55:05 am -
1 stop5h 06m
Deal found 9/30![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 10/296:55 am -
1 stop6h 26m
Sun 11/15:05 am -
1 stop6h 13m
Deal found 10/2![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:10 am -
1 stop5h 05m
Sun 11/15:50 am -
2 stops6h 10m
Deal found 10/2![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:55 pm -
2 stops7h 00m
Sun 11/15:50 am -
2 stops6h 10m
Deal found 10/2![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/215:15 pm -
1 stop5h 33m
Sun 11/299:20 pm -
1 stop5h 15m
Deal found 10/2![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:55 pm -
2 stops12h 25m
Thu 11/54:45 pm -
1 stop8h 25m
Deal found 9/30![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 11/66:55 am -
1 stop6h 26m
Sun 11/85:25 pm -
1 stop7h 20m
Deal found 10/2![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
1 stop5h 35m
Wed 10/214:35 pm -
1 stop4h 30m
Deal found 9/29![Southwest logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/2. 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 10/176:25 am -
1 stop6h 58m
Sun 10/185:18 pm -
1 stop7h 05m
Deal found 10/2![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:55 pm -
1 stop4h 50m
Tue 11/2411:50 am -
1 stop5h 55m
Deal found 9/29![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:30 am -
1 stop7h 53m
Wed 10/285:05 am -
1 stop5h 06m
Deal found 9/29![United Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:15 am -
1 stop4h 55m
Sun 11/155:50 pm -
2 stops7h 20m
Deal found 9/29![Southwest logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 12/145:45 am -
1 stop5h 29m
Mon 1/45:22 pm -
1 stop7h 22m
Deal found 10/3![United Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:35 am -
2 stops9h 05m
Wed 10/214:35 pm -
2 stops5h 25m
Deal found 10/2![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 9/30. 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 12/26:50 am -
1 stop6h 35m
Mon 12/74:39 pm -
2 stops16h 42m
Deal found 9/30![United Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/29. 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 11/122:12 pm -
2 stops23h 09m
Sun 11/155:25 pm -
1 stop6h 01m
Deal found 9/29![United Airlines logo]()
$532
Last-minute flights from Chicago to HarlingenDiscover last-minute flight deals from Chicago to Harlingen. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Harlingen. Data last updated October 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/103:50 pm -
1 stop7h 00m
Tue 10/136:42 pm -
1 stop5h 17m
Deal found 10/3![American Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
1 stop7h 51m
Thu 11/55:05 am -
1 stop5h 06m
Deal found 9/30![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:45 am -
1 stop4h 35m
Thu 11/54:45 pm -
1 stop8h 25m
Deal found 9/30![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:45 am -
1 stop4h 35m
Sun 11/15:50 am -
1 stop4h 30m
Deal found 10/2![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:55 pm -
2 stops7h 00m
Sun 11/15:50 am -
2 stops6h 10m
Deal found 10/2![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 11/66:55 am -
1 stop6h 26m
Sun 11/85:25 pm -
1 stop7h 20m
Deal found 10/2![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:40 am -
1 stop5h 30m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 9/29![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:20 am -
1 stop7h 00m
Wed 11/1811:35 am -
1 stop5h 35m
Deal found 10/1![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:52 pm -
1 stop7h 07m
Wed 11/182:26 pm -
1 stop5h 34m
Deal found 10/1![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:34 am -
1 stop5h 27m
Tue 11/241:59 pm -
1 stop7h 41m
Deal found 9/29![United Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/215:15 pm -
1 stop5h 33m
Sun 11/299:20 pm -
1 stop5h 15m
Deal found 10/2![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/29. 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 11/246:05 am -
1 stop8h 15m
Wed 12/26:41 pm -
1 stop5h 18m
Deal found 9/29![American Airlines logo]()
$350
One-way flights from Chicago to HarlingenSearch for one-way flight options from Chicago to Harlingen. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
Search for one-way flight options from Chicago to Harlingen. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:00 am -
1 stop5h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Southwest logo]()
$156
This Delta deal was found by Cheapflights users on 10/1. 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.
Mon 11/26:20 am -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$170
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:30 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Southwest logo]()
$170
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Wed 10/145:30 am -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:30 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Southwest logo]()
$195
This Sun Country Air deal was found by Cheapflights users on 9/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/3111:53 am -
1 stop22h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Sun Country Air logo]()
$198
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:15 pm -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Southwest logo]()
$200
This United Airlines deal was found by Cheapflights users on 9/30. 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 3/294:57 pm -
1 stop4h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$203
This United Airlines deal was found by Cheapflights users on 10/2. 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 1/27:40 am -
1 stop8h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$205
This Sun Country Air deal was found by Cheapflights users on 9/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/111:45 am -
1 stop22h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Sun Country Air logo]()
$208
This United Airlines deal was found by Cheapflights users on 9/30. 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 3/312:15 pm -
1 stop7h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$211
Find flight deals from Chicago to Harlingen
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Harlingen (HRL). 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 October 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (American Airlines) |
One-way from | $156 (American Airlines) |
Popular in | October |
Cheapest in | May |
Average price | $518 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Harlingen 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 October 4, 2026.
Use the filters below to find and compare flights from Chicago to Harlingen that are best for you.
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Route
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Cheapest round-trip
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Sat 10/31
7:25 am-1:05 pm
1 stop5h 40m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$156
Quickest round-trip
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Thu 4/1
4:57 pm-9:44 pm
1 stop4h 47m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Mon 11/2
6:20 am-1:23 pm
1 stop7h 03m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Fri 11/6
6:20 am-1:23 pm
1 stop7h 03m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Fri 4/2
4:57 pm-9:44 pm
1 stop4h 47m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Tue 10/27
3:30 pm-9:00 pm
1 stop5h 30m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Sun 3/28
4:05 pm-9:44 pm
1 stop5h 39m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Fri 1/8
9:18 am-3:53 pm
1 stop6h 35m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Tue 10/20
3:30 pm-9:00 pm
1 stop5h 30m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$195
ChicagoHarlingen
ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl
ORDHRL
Chicago O'Hare Intl
Thu 12/31
11:53 am-10:49 am
1 stop22h 56m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Chicago to Harlingen
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 Harlingen in October.
| 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-Harlingen flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Harlingen flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Harlingen flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Harlingen 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-Harlingen 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 Harlingen
Have a flexible travel schedule? Discover the best time to fly to Harlingen from Chicago with our price prediction graph.
CHI-HRL
ORD-HRL
MDW-HRL
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 Harlingen
CHI-HRL
ORD-HRL
MDW-HRL
What is the cheapest month to book a flight from Chicago to Harlingen?
Currently, May is the cheapest month in which you can book a flight from Chicago to Harlingen (average of $311). Flying from Chicago to Harlingen in September is currently the most expensive (average of $488). 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.
Reviews of airlines servicing Harlingen
Get insights into the airlines that provide service to Harlingen. 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 Harlingen. Reviews last updated October 4, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Harlingen to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Harlingen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Search flights from Chicago to Harlingen by cabin class
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Other flights to Harlingen
Explore flights to Harlingen departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 4, 2026.
Chicago and Harlingen flights
Browse other Chicago and Harlingen flight options. Last updated on October 4, 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 October 4, 2026.
Popular flight searches
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Top 3 airlines flying from Chicago to Harlingen
Discover the top 3 airlines that operate flights from Chicago to Harlingen. 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 October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$348 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$255 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$367 | FlexibilityNo cancel fee | On-time71% |