HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Harlingen

$160+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HRL
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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.

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 June 24, 2026.

This American Airlines deal was found by Cheapflights users on 6/23. 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 9/2211:00 am
ORD
-
HRL
1 stop5h 58m
American Airlines
Sat 9/263:35 pm
HRL
-
ORD
1 stop6h 29m
American Airlines
Deal found 6/23$257
This United Airlines deal was found by Cheapflights users on 6/21. 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 8/148:50 am
ORD
-
HRL
1 stop7h 09m
United Airlines
Sat 8/295:18 pm
HRL
-
ORD
1 stop6h 08m
United Airlines
Deal found 6/21$293
This American Airlines deal was found by Cheapflights users on 6/24. 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 8/75:00 am
ORD
-
HRL
1 stop5h 04m
American Airlines
Sat 8/153:17 pm
HRL
-
ORD
1 stop5h 59m
American Airlines
Deal found 6/24$328
This American Airlines deal was found by Cheapflights users on 6/23. 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 8/1412:11 pm
ORD
-
HRL
1 stop6h 02m
American Airlines
Fri 8/216:43 pm
HRL
-
ORD
1 stop5h 35m
American Airlines
Deal found 6/23$329
This American Airlines deal was found by Cheapflights users on 6/23. 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 8/15:00 am
ORD
-
HRL
1 stop5h 12m
American Airlines
Sat 8/153:17 pm
HRL
-
ORD
1 stop5h 59m
American Airlines
Deal found 6/23$358
This American Airlines deal was found by Cheapflights users on 6/22. 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 7/235:00 am
ORD
-
HRL
1 stop5h 12m
American Airlines
Sun 7/266:00 am
HRL
-
ORD
1 stop5h 10m
American Airlines
Deal found 6/22$366
This United Airlines deal was found by Cheapflights users on 6/22. 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 11/177:40 am
ORD
-
HRL
1 stop8h 20m
United Airlines
Wed 11/185:05 am
HRL
-
ORD
1 stop5h 06m
United Airlines
Deal found 6/22$378
This United Airlines deal was found by Cheapflights users on 6/23. 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 8/62:15 pm
ORD
-
HRL
1 stop7h 39m
United Airlines
Fri 8/145:18 pm
HRL
-
ORD
1 stop6h 08m
United Airlines
Deal found 6/23$385
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/285:00 am
ORD
-
HRL
1 stop5h 12m
American Airlines
Tue 8/44:58 pm
HRL
-
ORD
1 stop7h 45m
American Airlines
Deal found 6/21$388
This Delta deal was found by Cheapflights users on 6/22. 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.
Tue 11/246:00 am
ORD
-
HRL
1 stop7h 31m
Delta
Wed 12/22:00 pm
HRL
-
ORD
2 stops9h 50m
Delta
Deal found 6/22$393
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/112:15 pm
ORD
-
HRL
1 stop7h 39m
United Airlines
Sat 7/187:20 am
HRL
-
ORD
1 stop5h 09m
United Airlines
Deal found 6/20$399

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(American Airlines)

One-way from

$160
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$393
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 ($31 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 June 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 June 24, 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

Tue 8/18

8:50 am-3:59 pm

1 stop7h 09m

Harlingen Valley Intl

Tue 8/25

5:18 pm-11:26 pm

1 stop6h 08m

$257

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 11/17

7:40 am-4:00 pm

1 stop8h 20m

Harlingen Valley Intl

Wed 11/18

5:05 am-10:11 am

1 stop5h 06m

$378

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 8/28

6:30 am-1:24 pm

1 stop6h 54m

Harlingen Valley Intl

Tue 9/1

1:59 pm-9:32 pm

1 stop7h 33m

$388

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 9/22

8:50 am-3:59 pm

1 stop7h 09m

Harlingen Valley Intl

Sat 9/26

7:15 am-8:30 pm

2 stops13h 15m

$411

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 11/24

11:46 am-7:30 pm

1 stop7h 44m

Harlingen Valley Intl

Wed 12/2

4:02 pm-10:19 pm

1 stop6h 17m

$412
Cheapest one-way

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 8/19

8:50 am-3:59 pm

1 stop7h 09m

$174
Quickest one-way

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 7/25

5:00 am-10:12 am

1 stop5h 12m

$209

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 6/30

2:15 pm-7:49 pm

1 stop5h 34m

$238

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 9/22

8:30 pm-3:59 pm

2 stops19h 29m

$244

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 11/24

8:34 pm-11:19 am

1 stop14h 45m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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 June.
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 May is currently the most expensive (average of $296). 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?

What’s the top layover airport for flights from Chicago to Harlingen?

Share of 1-stop round-trip flights from Chicago to Harlingen chosen by Cheapflights users in the past 12 months, using the same layover each way.

Houston (IAH) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Harlingen on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Harlingen?

Average round-trip fare for 1-stop flights from Chicago to Harlingen, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Austin (AUS) is the most affordable 1-stop option, with an average round-trip price of $310.

What’s the fastest layover option from Chicago to Harlingen?

Shortest average travel time for 1-stop one-way flights from Chicago to Harlingen, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Austin (AUS) have the shortest average one-way travel time for 1-stop routes: 4h 30m.

Which airport typically offers the quickest layover for flights from Chicago to Harlingen?

Average layover duration for 1-stop one-way flights from Chicago to Harlingen, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Austin (AUS) offer the fastest connection on this route, with an average layover time of 1h 03m.

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 June 24, 2026.
Peruse reviews from past customers who have flown with Southwest and United 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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

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
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

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
9,881 reviews
Southwest
7.9
Good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

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?

    United Airlines can get you from Chicago to Harlingen in just under 7h 09m. Your travel time can differ by up to . There are 1220 mi between Chicago and Harlingen.

  • 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 ($255) offers the cheapest pricing from Chicago to Harlingen. These flights start at 41% 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 May is currently the most expensive (average of $296). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Harlingen

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Hobby flights
O'Hare Intl to George Bush Intcntl flights
Midway to Hobby flights
O'Hare Intl to Austin flights
Midway to George Bush Intcntl flights
O'Hare Intl to San Antonio flights
St. Louis to Dallas/Fort Worth flights
St. Louis to Hobby flights
St. Louis to George Bush Intcntl flights
Midway to Love Field flights
Midway to Austin flights
O'Hare Intl to El Paso flights
Peoria to Dallas/Fort Worth flights
O'Hare Intl to Love Field flights
Midway to San Antonio flights
Moline to Dallas/Fort Worth flights
St. Louis to Love Field flights
St. Louis to San Antonio flights
St. Louis to Austin flights
Bloomington to Dallas/Fort Worth flights
Midway to El Paso flights
Moline to Hobby flights
Moline to George Bush Intcntl flights
O'Hare Intl to Corpus Christi flights
Springfield to Dallas/Fort Worth flights
O'Hare Intl to McAllen flights
Moline to San Antonio flights
St. Louis to Lubbock flights
Peoria to San Antonio flights
Moline to Austin flights
Decatur to Dallas/Fort Worth flights
Bloomington to Love Field flights
St. Louis to Amarillo flights
Evansville to Hobby flights
O'Hare Intl to Harlingen flights
St. Louis to McAllen flights
Bloomington to San Antonio flights
Evansville to Dallas/Fort Worth flights
Peoria to Hobby flights
St. Louis to El Paso flights
Champaign to Dallas/Fort Worth flights
O'Hare Intl to Midland flights
Peoria to Austin flights
Peoria to George Bush Intcntl flights
Moline to McAllen flights
Bloomington to Austin flights

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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$348FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$233Average$330FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$255Average$359FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.