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$160+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$248
(Southwest)

One-way from

$160
(Southwest)

Popular in

June

Cheapest in

May

Average price

$545
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. 17% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/12. 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 8/2012:20 pmHRL - ORD
1 stop9h 10mSouthwest
Sun 8/247:30 amORD - HRL
1 stop6h 40mSouthwest
Deal found 6/12$248
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/135:25 amHRL - ORD
1 stop6h 57mAmerican Airlines
Fri 8/2210:25 amORD - HRL
1 stop7h 35mAmerican Airlines
Deal found 6/10$288
This eDestinos deal was found by Cheapflights users on 6/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2312:10 pmHRL - ORD
1 stop6h 30mSun Country Air
Fri 11/289:10 pmORD - HRL
1 stop13h 21mSun Country Air
Deal found 6/11$304
This United Airlines deal was found by Cheapflights users on 6/10. 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 10/25:27 pmHRL - ORD
1 stop6h 47mUnited Airlines
Sun 10/57:10 amORD - HRL
1 stop6h 09mUnited Airlines
Deal found 6/10$363

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 June 12, 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

Wed 8/20

12:20 pm-9:30 pm

1 stop9h 10m

Chicago O'Hare Intl

Sun 8/24

7:30 am-2:10 pm

1 stop6h 40m

$248

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 8/13

5:25 am-12:22 pm

1 stop6h 57m

Chicago O'Hare Intl

Fri 8/22

10:25 am-6:00 pm

1 stop7h 35m

$288

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sun 11/23

12:10 pm-6:40 pm

1 stop6h 30m

Chicago O'Hare Intl

Fri 11/28

9:10 pm-10:31 am

1 stop13h 21m

$304

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 10/2

5:27 pm-12:14 am

1 stop6h 47m

Chicago O'Hare Intl

Sun 10/5

7:10 am-1:19 pm

1 stop6h 09m

$363

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 7/21

7:59 pm-12:59 am

1 stop5h 00m

$175

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 7/21

5:20 pm-9:38 am

2 stops16h 18m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 12, 2025.

It’s optimal to fly from Harlingen, Texas to Chicago in the morning. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight at noon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
See what other customers who have flown with Southwest, United Airlines and American Airlines from Harlingen to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

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
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

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.
Sun Country Air
6.9
Okay
345 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

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 Southwest. Our recent data shows that you can find tickets from as low as $248 on this airline. Additional options worth looking into are American Airlines and Sun Country Air, starting at $288 and $304 round-trip. Southwest is priced at 26% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Harlingen, Texas to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $160. Users have also found prices from $175 and $253 on American Airlines and United Airlines, respectively.

  • 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 Harlingen?

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

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Alternative routes for Harlingen to Chicago

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$360FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$263Average$313FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$288Average$397FlexibilityNo cancel feeOn-time69%

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