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$126+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$247
(Southwest)

One-way from

$126
(American Airlines)

Popular in

June

Cheapest in

May

Average price

$299
From Harlingen Valley Intl to Chicago (CHI)
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One-way flight from Harlingen Valley Intl to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 10/1410:40 amHRL - ORD
1 stop10h 50mSouthwest
Tue 10/214:20 pmORD - HRL
1 stop5h 20mSouthwest
Deal found 9/14$247
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/286:37 pmHRL - ORD
1 stop5h 05mAmerican Airlines
Wed 11/58:10 amORD - HRL
1 stop7h 22mAmerican Airlines
Deal found 9/13$251
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/146:40 pmHRL - ORD
1 stop4h 57mAmerican Airlines
Mon 11/177:25 amORD - HRL
1 stop8h 07mAmerican Airlines
Deal found 9/14$269
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/292:50 pmHRL - ORD
1 stop6h 24mAmerican Airlines
Tue 11/48:50 amORD - HRL
1 stop6h 42mAmerican Airlines
Deal found 9/14$285
This Sun Country Air deal was found by Cheapflights users on 9/15. 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.
Mon 12/2911:13 amHRL - ORD
1 stop7h 25mSun Country Air
Sun 1/47:50 pmORD - HRL
1 stop14h 57mSun Country Air
Deal found 9/15$292
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/302:51 pmHRL - ORD
1 stop6h 54mAmerican Airlines
Sat 10/41:20 pmORD - HRL
1 stop4h 45mAmerican Airlines
Deal found 9/15$319
This Southwest deal was found by Cheapflights users on 9/15. 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 10/287:30 amHRL - ORD
1 stop8h 55mSouthwest
Wed 11/52:15 pmORD - HRL
2 stops7h 40mSouthwest
Deal found 9/15$328
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/305:23 amHRL - ORD
1 stop5h 36mAmerican Airlines
Sun 11/25:18 amORD - HRL
1 stop6h 20mAmerican Airlines
Deal found 9/14$329
This Southwest deal was found by Cheapflights users on 9/14. 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 10/296:40 amHRL - ORD
2 stops8h 40mSouthwest
Tue 11/42:15 pmORD - HRL
2 stops7h 40mSouthwest
Deal found 9/14$334
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/134:02 pmHRL - ORD
1 stop7h 29mAmerican Airlines
Mon 11/177:25 amORD - HRL
1 stop8h 07mAmerican Airlines
Deal found 9/14$343

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 September 15, 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 10/14

10:40 am-9:30 pm

1 stop10h 50m

Chicago O'Hare Intl

Tue 10/21

4:20 pm-9:40 pm

1 stop5h 20m

$247

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 10/29

7:30 am-4:25 pm

1 stop8h 55m

Chicago O'Hare Intl

Tue 11/4

2:15 pm-9:55 pm

2 stops7h 40m

$253

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 11/14

6:40 pm-11:37 pm

1 stop4h 57m

Chicago O'Hare Intl

Mon 11/17

7:25 am-3:32 pm

1 stop8h 07m

$269

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 10/29

2:50 pm-9:14 pm

1 stop6h 24m

Chicago O'Hare Intl

Tue 11/4

8:50 am-3:32 pm

1 stop6h 42m

$285

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 12/29

11:13 am-6:38 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 1/4

7:50 pm-10:47 am

1 stop14h 57m

$292

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 2/24

5:50 am-6:00 pm

2 stops12h 10m

Chicago O'Hare Intl

Wed 2/25

5:00 am-11:39 am

1 stop6h 39m

$316

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 10/30

6:00 am-3:20 pm

2 stops9h 20m

Chicago O'Hare Intl

Sun 11/2

2:15 pm-11:35 pm

2 stops9h 20m

$319

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/30

2:51 pm-9:45 pm

1 stop6h 54m

Chicago O'Hare Intl

Sat 10/4

1:20 pm-6:05 pm

1 stop4h 45m

$319

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 10/28

7:30 am-4:25 pm

1 stop8h 55m

Chicago O'Hare Intl

Tue 11/4

2:15 pm-9:55 pm

2 stops7h 40m

$328

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 10/15

6:37 pm-11:42 pm

1 stop5h 05m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 12 results
1
2

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 September 15, 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.

How much does it cost to fly round-trip from Harlingen, Texas to Chicago?

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 September 15, 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
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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.

  • How long is the flight from Harlingen, Texas to Chicago?

    Southwest and American Airlines can get you from Harlingen, Texas to Chicago in just under 4h 57m. Your travel time can differ by up to 5h 53m. Harlingen, Texas and Chicago are separated by a distance of 1220 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $252 and $288 round-trip. American Airlines is priced at 33% 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
Chesterton

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Alternative routes for Harlingen to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$392FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$252Average$319FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$288Average$393FlexibilityNo cancel feeOn-time69%

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