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Harlingen

$200+ Cheap flights from Chicago (CHI) to Harlingen (HRL)

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HRL
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheap flight deals from Chicago to Harlingen

Cheapest flights from Chicago to Harlingen
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 May 7, 2026.

This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:13 pm
ORD
-
HRL
1 stop5h 16m
United Airlines
Sat 8/222:00 pm
HRL
-
ORD
1 stop7h 37m
United Airlines
Deal found 5/3$269
This American Airlines deal was found by Cheapflights users on 5/4. 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 8/155:00 am
ORD
-
HRL
1 stop5h 04m
American Airlines
Sat 8/2210:34 am
HRL
-
ORD
1 stop8h 01m
American Airlines
Deal found 5/4$285
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 5/195:00 am
ORD
-
HRL
1 stop5h 17m
American Airlines
Sat 5/235:18 pm
HRL
-
ORD
1 stop7h 24m
American Airlines
Deal found 5/4$308
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Wed 5/65:00 am
ORD
-
HRL
1 stop5h 17m
American Airlines
Sat 5/92:51 pm
HRL
-
ORD
1 stop6h 23m
American Airlines
Deal found 5/4$309
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:45 pm
ORD
-
HRL
1 stop5h 10m
Southwest
Sat 5/96:05 am
HRL
-
ORD
2 stops15h 50m
Southwest
Deal found 5/4$320
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/306:32 pm
ORD
-
HRL
1 stop5h 42m
American Airlines
Sat 6/65:18 pm
HRL
-
ORD
1 stop5h 17m
American Airlines
Deal found 5/3$324
This United Airlines deal was found by Cheapflights users on 5/5. 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 9/117:30 am
ORD
-
HRL
1 stop8h 04m
United Airlines
Sun 9/135:15 am
HRL
-
ORD
1 stop4h 59m
United Airlines
Deal found 5/5$326
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:32 pm
ORD
-
HRL
1 stop5h 42m
American Airlines
Thu 5/284:57 pm
HRL
-
ORD
1 stop7h 45m
American Airlines
Deal found 5/7$336
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:05 pm
ORD
-
HRL
2 stops7h 30m
Southwest
Fri 5/156:55 am
HRL
-
ORD
1 stop6h 20m
Southwest
Deal found 5/4$378
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:05 pm
ORD
-
HRL
2 stops7h 30m
Southwest
Thu 5/286:55 am
HRL
-
ORD
1 stop6h 20m
Southwest
Deal found 5/7$381

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$200
(United Airlines)

Popular in

March

Cheapest in

November

Average price

$311
Provider with most accurate pricing for Chicago (CHI)-Harlingen Valley Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Harlingen Valley Intl flights.
Search Deals
From Chicago (CHI) to Harlingen Valley Intl
Search Deals
One-way flight from Chicago (CHI) to Harlingen Valley Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 2,558,603 searches. Data last updated May 7, 2026.
Use the filters below to find and compare flights from Chicago to Harlingen that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 8/15

5:00 am-10:04 am

1 stop5h 04m

Harlingen Valley Intl

Sat 8/22

6:43 pm-11:58 pm

1 stop5h 15m

$285

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 5/30

6:32 pm-12:14 am

1 stop5h 42m

Harlingen Valley Intl

Sat 6/6

5:18 pm-10:35 pm

1 stop5h 17m

$324

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Thu 6/11

7:30 am-1:30 pm

1 stop6h 00m

Harlingen Valley Intl

Mon 6/15

5:20 pm-12:45 am

1 stop7h 25m

$348

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 6/1

3:45 pm-8:35 pm

1 stop4h 50m

Harlingen Valley Intl

Wed 6/3

7:10 am-1:15 pm

1 stop6h 05m

$414

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 9/1

7:30 am-3:34 pm

1 stop8h 04m

Harlingen Valley Intl

Sat 9/5

5:16 pm-12:48 am

1 stop7h 32m

$429

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 5/22

3:45 pm-8:35 pm

1 stop4h 50m

Harlingen Valley Intl

Sun 5/24

7:55 am-6:50 pm

1 stop10h 55m

$466

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 8/15

7:00 am-7:29 pm

2 stops12h 29m

Harlingen Valley Intl

Sat 8/22

2:00 pm-9:37 pm

1 stop7h 37m

$490
Cheapest one-way
Quickest one-way

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 5/12

2:05 pm-9:59 pm

1 stop7h 54m

$200

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 8/17

7:30 am-3:34 pm

1 stop8h 04m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Sorted 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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

What is the cheapest month to book a flight from Chicago to Harlingen?

Currently, January is the cheapest month in which you can book a flight from Chicago to Harlingen (average of $134). Flying from Chicago to Harlingen in November is currently the most expensive (average of $291). 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 Chicago to Harlingen?

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 May 7, 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.
Southwest
7.9
Good
4,301 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,690 reviews
Southwest
7.9
Good
4,301 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.1
Good
11,669 reviews
Southwest
7.9
Good
4,301 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly into for flights to Harlingen from Chicago?

    Located just 3.7 mi from the city center, Harlingen Valley Intl is the airport most travelers will use when flying to Harlingen from Chicago. Booking flights from Chicago to Valley Intl (HRL) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Harlingen?

    American Airlines, Southwest, and United Airlines can get you from Chicago to Harlingen in just under 4h 50m. Your travel time can differ by up to 3h 14m. There are 1220 mi between Chicago and Harlingen. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Harlingen round-trip?

    According to our current data, Southwest ($216), American Airlines ($233), and United Airlines ($251) offers the cheapest pricing from Chicago to Harlingen. These flights start at 42% lower than the current average price 3 months from now.

  • Can I find deals for flights from Chicago to Harlingen that include hotel bookings?

    Yes. In addition to deals on Chicago to Harlingen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Harlingen?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Harlingen.

  • Can I find deals for business class flights from Chicago to Harlingen?

    Yes. Cheapflights offers flight deals from Chicago to Harlingen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Harlingen?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Harlingen (average of $134). Flying from Chicago to Harlingen in November is currently the most expensive (average of $291). 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.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 2,558,603 searches. Data last updated May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$348FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$233Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$251Average$359FlexibilityNo cancel feeOn-time69%

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