HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$119+ Cheap flights from Harlingen, TX (HRL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Harlingen to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 July 31, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$343
From Harlingen Valley Intl to Chicago (CHI)
Search Deals
One-way flight from Harlingen Valley Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Harlingen to Chicago

Cheapest flights from Harlingen to Chicago
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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/31. 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 9/97:25 amHRL - ORD
1 stop7h 55mSouthwest
Tue 9/167:30 amORD - HRL
1 stop6h 05mSouthwest
Deal found 7/31$217
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/196:30 pmHRL - ORD
1 stop15h 31mAmerican Airlines
Sat 8/2310:25 amORD - HRL
1 stop7h 35mAmerican Airlines
Deal found 7/29$282
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/95:00 amHRL - ORD
2 stops13h 55mUnited Airlines
Tue 9/164:50 pmORD - HRL
1 stop5h 02mUnited Airlines
Deal found 7/31$347

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 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.

Fly from

Harlingen

Fly to

Chicago

Route

Depart

Return

Price

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

2:51 pm-8:01 pm

1 stop5h 10m

Chicago O'Hare Intl

Tue 9/16

3:08 pm-10:57 pm

1 stop7h 49m

$217

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

7:25 am-3:20 pm

1 stop7h 55m

Chicago O'Hare Intl

Tue 9/16

4:20 pm-9:25 pm

1 stop5h 05m

$237

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

5:00 am-6:55 pm

2 stops13h 55m

Chicago O'Hare Intl

Tue 9/16

4:50 pm-9:52 pm

1 stop5h 02m

$347

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/30

5:45 am-11:00 am

1 stop5h 15m

$119

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/30

11:15 am-9:30 pm

2 stops10h 15m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.
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

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

Currently, August is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $245). Flying from Harlingen, Texas to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HRL to CHI?

Find hourly flight availability from Harlingen to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

It’s optimal to fly from Harlingen, Texas to Chicago in the morning. By choosing this option you can save up to 49% on the cost of your flight, compared to a flight at noon.

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 July 31, 2025.
Read through reviews of airlines operating flights from Harlingen to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    Harlingen Valley Intl (HRL), located 3.7 mi from the city center, is the airport you fly out of when you book flights from Harlingen to Chicago. 3 airlines have flights from Valley Intl to Chicago on a regular basis. Booking flights from Harlingen Valley Intl to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

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

    Our cheapest airline available from Harlingen, Texas to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $217 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $237 and $347 round-trip. American Airlines is priced at 31% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Harlingen to Chicago 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 Harlingen, Texas to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $245). Flying from Harlingen, Texas to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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 Harlingen to Chicago

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

Top 3 airlines flying from Harlingen to Chicago

Discover the top 3 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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$387FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$263Average$313FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$288Average$393FlexibilityNo 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.