$153+ Cheap flights from Harlingen (HRL) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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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 Harlingen to ChicagoExplore the most affordable flight options available from Harlingen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2026.
Explore the most affordable flight options available from Harlingen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 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.
Fri 10/305:05 am -
1 stop5h 06m
Tue 11/105:30 pm -
1 stop5h 18m
Deal found 9/29![United Airlines logo]()
$325
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.
Fri 10/305:30 pm -
1 stop7h 00m
Tue 11/106:40 am -
1 stop5h 30m
Deal found 9/29![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/296:30 pm -
2 stops6h 40m
Wed 11/46:40 am -
1 stop5h 30m
Deal found 9/28![Southwest logo]()
$330
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.
Fri 10/235:30 pm -
1 stop7h 00m
Sun 10/255:25 am -
1 stop4h 15m
Deal found 9/29![Southwest logo]()
$334
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 11/54:45 pm -
1 stop8h 25m
Wed 11/117:05 am -
2 stops8h 45m
Deal found 9/30![Southwest logo]()
$336
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:13 pm -
1 stop5h 25m
Sun 10/256:20 am -
1 stop7h 03m
Deal found 9/29![Delta logo]()
$339
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.
Fri 11/65:50 pm -
1 stop6h 20m
Mon 11/95:15 am -
1 stop4h 55m
Deal found 9/29![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/216:25 pm -
1 stop6h 25m
Tue 11/246:30 am -
1 stop4h 40m
Deal found 9/26![Southwest logo]()
$346
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.
Sun 11/15:50 am -
1 stop4h 30m
Sun 11/85:15 am -
1 stop4h 55m
Deal found 9/30![Southwest logo]()
$360
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 10/102:00 pm -
1 stop7h 42m
Sat 10/247:30 am -
1 stop5h 53m
Deal found 9/29![United Airlines logo]()
$364
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.
Fri 11/136:41 pm -
1 stop5h 18m
Sun 11/156:59 am -
1 stop6h 57m
Deal found 9/29![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/212:50 pm -
1 stop7h 43m
Tue 11/246:05 am -
1 stop8h 15m
Deal found 9/26![American Airlines logo]()
$379
Best flights from Harlingen to ChicagoDiscover carefully curated flight deals from Harlingen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
Discover carefully curated flight deals from Harlingen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:00 pm -
1 stop6h 20m
Tue 1/129:15 am -
1 stop6h 19m
Deal found 10/1![United Airlines 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.
Sat 12/1212:45 pm -
1 stop5h 25m
Tue 1/1212:25 pm -
2 stops8h 10m
Deal found 10/1![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/232:13 pm -
1 stop5h 25m
Sun 10/256:20 am -
1 stop7h 03m
Deal found 9/26![Delta logo]()
$339
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 11/55:05 am -
1 stop5h 06m
Wed 11/116:55 am -
1 stop6h 26m
Deal found 9/30![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/296:30 pm -
2 stops6h 40m
Wed 11/46:40 am -
1 stop5h 30m
Deal found 9/28![Southwest logo]()
$330
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 11/54:45 pm -
1 stop8h 25m
Wed 11/117:05 am -
2 stops8h 45m
Deal found 9/30![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:05 am -
1 stop5h 05m
Sun 11/159:21 am -
1 stop6h 40m
Deal found 9/26![United Airlines logo]()
$399
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.
Sun 11/15:50 am -
2 stops6h 10m
Sun 11/85:15 am -
1 stop4h 55m
Deal found 9/30![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/82:13 pm -
1 stop5h 25m
Sun 10/116:20 am -
1 stop7h 03m
Deal found 9/27![Delta logo]()
$446
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.
Tue 11/101:59 pm -
1 stop7h 41m
Wed 11/119:21 am -
1 stop6h 40m
Deal found 9/30![United Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/235:30 pm -
1 stop7h 00m
Sun 10/255:25 am -
1 stop4h 15m
Deal found 9/26![Southwest logo]()
$423
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/205:25 pm -
1 stop7h 20m
Sat 11/216:55 am -
1 stop6h 26m
Deal found 9/26![United Airlines logo]()
$432
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.
Sat 12/196:25 pm -
1 stop6h 20m
Tue 12/226:10 pm -
1 stop5h 55m
Deal found 9/30![Southwest logo]()
$439
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/135:50 pm -
1 stop6h 20m
Sun 11/157:20 am -
1 stop5h 00m
Deal found 9/26![Southwest logo]()
$459
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/235:18 pm -
2 stops17h 22m
Sun 10/255:30 am -
1 stop5h 20m
Deal found 9/26![United Airlines logo]()
$532
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.
Fri 10/161:50 pm -
1 stop7h 35m
Mon 10/197:15 am -
1 stop6h 00m
Deal found 9/29![Southwest logo]()
$468
Last-minute flights from Harlingen to ChicagoDiscover last-minute flight deals from Harlingen to Chicago. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Harlingen to Chicago. Data last updated October 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/14:53 pm -
1 stop7h 21m
Tue 10/65:00 am -
1 stop5h 08m
Deal found 9/26![American Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/33:35 pm -
1 stop5h 34m
Tue 10/65:00 am -
1 stop5h 08m
Deal found 9/28![American Airlines logo]()
$388
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.
Sat 10/35:28 pm -
1 stop6h 02m
Wed 10/75:00 am -
1 stop5h 08m
Deal found 9/30![American Airlines logo]()
$389
This SmartFares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:13 pm -
1 stop5h 25m
Sun 10/116:20 am -
1 stop7h 03m
Deal found 9/26![Delta logo]()
$409
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 10/102:00 pm -
1 stop7h 42m
Sat 10/247:30 am -
1 stop5h 53m
Deal found 9/29![United Airlines logo]()
$364
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.
Sat 10/103:15 pm -
1 stop4h 45m
Sat 10/243:10 pm -
1 stop5h 50m
Deal found 9/29![Southwest logo]()
$393
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.
Fri 10/235:30 pm -
1 stop7h 00m
Sun 10/255:25 am -
1 stop4h 15m
Deal found 9/29![Southwest logo]()
$334
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:13 pm -
1 stop5h 25m
Sun 10/256:20 am -
1 stop7h 03m
Deal found 9/29![Delta logo]()
$339
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.
Fri 10/235:30 pm -
1 stop7h 00m
Mon 10/267:10 am -
1 stop5h 05m
Deal found 9/29![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/296:30 pm -
2 stops6h 40m
Wed 11/46:40 am -
1 stop5h 30m
Deal found 9/28![Southwest logo]()
$330
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.
Fri 10/305:05 am -
1 stop5h 06m
Tue 11/105:30 pm -
1 stop5h 18m
Deal found 9/29![United Airlines logo]()
$325
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.
Fri 10/305:30 pm -
1 stop7h 00m
Tue 11/106:40 am -
1 stop5h 30m
Deal found 9/29![Southwest logo]()
$325
One-way flights from Harlingen to ChicagoSearch for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
Search for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:41 am -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Sun Country Air logo]()
$153
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/271:59 pm -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![United Airlines logo]()
$156
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/265:22 pm -
1 stop6h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![United Airlines logo]()
$160
This Sun Country Air deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 12/2512:34 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Sun Country Air logo]()
$163
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:13 pm -
1 stop7h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Delta logo]()
$170
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.
Fri 11/65:50 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/256:22 pm -
2 stops30h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$178
This Sun Country Air deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/2211:50 am -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Sun Country Air logo]()
$183
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/276:15 am -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Southwest logo]()
$191
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2910:52 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Sun Country Air logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/106:42 pm -
1 stop5h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![American Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/102:13 pm -
2 stops9h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$200
Find flight deals from Harlingen to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Harlingen (HRL) 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 October 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Southwest) |
One-way from | $153 (Sun Country Air) |
Popular in | January |
Cheapest in | November |
Average price | $468 |
Cheapflights Fare Finder
Customize your flight search to find flights from Harlingen to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 1, 2026.
Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Thu 10/29
11:41 am-6:18 pm
1 stop6h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$153
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Mon 12/28
11:10 am-6:40 pm
1 stop7h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$163
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Fri 10/23
2:13 pm-9:27 pm
1 stop7h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Wed 10/28
1:59 pm-7:55 pm
1 stop5h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Fri 10/30
2:13 pm-11:57 pm
2 stops9h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
Quickest round-trip
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Wed 11/25
5:05 am-10:11 am
1 stop5h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Wed 12/2
12:00 pm-6:20 pm
1 stop6h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Tue 12/22
5:22 pm-12:44 am
1 stop7h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
HarlingenChicago
HRL Harlingen Valley Intl - MDW Chicago Midway
HRLMDW
Harlingen Valley Intl
Sat 10/10
3:15 pm-10:20 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Sun 10/25
5:25 pm-12:45 am
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$225
Showing 1-10 of 29 resultsSorted by cheapest first
Compare providers for flights from Harlingen 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 Harlingen to Chicago 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 Harlingen-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Harlingen-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Harlingen-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Harlingen-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 Harlingen-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 Harlingen to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Harlingen with our price prediction graph.
HRL-CHI
HRL-ORD
HRL-MDW
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 Harlingen to Chicago
HRL-CHI
HRL-ORD
HRL-MDW
What is the cheapest month to book a flight from Harlingen to Chicago?
Currently, May is the cheapest month in which you can book a flight from Harlingen to Chicago (average of $298). Flying from Harlingen to Chicago in March is currently the most expensive (average of $540). 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.
How much does it cost to fly round-trip from Harlingen to Chicago?
Airfare is below average for this route at the moment.
Harlingen to Chicago flights typically cost between $336 and $512 in December.The cheapest round-trip price found within the last 5 days was $306 on Southwest (Dec 12-Jan 12).
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 October 1, 2026.
Read through reviews of airlines operating flights from Harlingen to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Harlingen 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
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 1, 2026.
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Harlingen and Chicago flights
Browse other Harlingen and Chicago flight options. Last updated on October 1, 2026.
Other flights from Harlingen
Browse through other flights departing from Harlingen. Flights are based on user searches made on Cheapflights and were last updated on October 1, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Harlingen to Chicago
Discover the top 2 airlines that operate flights from Harlingen to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$401 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$290 | Average$384 | FlexibilityNo cancel fee | On-time71% |