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$140+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$140
(United Airlines)

Popular in

June

Cheapest in

May

Average price

$316
Provider with most accurate pricing for Harlingen Valley Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Harlingen Valley Intl-Chicago (CHI) flights.
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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 ($20 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 October 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 12/36:10 pmHRL - ORD
1 stop5h 25mAmerican Airlines
Wed 12/107:15 amORD - HRL
1 stop8h 15mAmerican Airlines
Deal found 10/28$251
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:49 amHRL - ORD
1 stop28h 53mMultiple Airlines
Thu 1/16:14 pmORD - HRL
1 stop16h 39mMultiple Airlines
Deal found 10/29$274
This Sun Country Air deal was found by Cheapflights users on 10/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:37 pmHRL - ORD
1 stop6h 07mSun Country Air
Tue 12/306:44 pmORD - HRL
1 stop16h 09mSun Country Air
Deal found 10/29$315
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/1212:10 pmHRL - ORD
1 stop7h 46mUnited Airlines
Sun 11/166:00 amORD - HRL
1 stop4h 59mUnited Airlines
Deal found 10/28$339
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/135:00 pmHRL - ORD
1 stop7h 15mUnited Airlines
Mon 11/172:21 pmORD - HRL
1 stop7h 33mUnited Airlines
Deal found 10/28$359
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 12/35:00 pmHRL - ORD
1 stop5h 56mUnited Airlines
Wed 12/105:50 pmORD - HRL
2 stops22h 09mUnited Airlines
Deal found 10/28$367
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/116:40 pmHRL - ORD
1 stop4h 57mAmerican Airlines
Sat 11/158:50 amORD - HRL
1 stop6h 42mAmerican Airlines
Deal found 10/29$374
This Sun Country Air deal was found by Cheapflights users on 10/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2211:43 amHRL - ORD
1 stop22h 43mSun Country Air
Fri 1/211:51 amORD - HRL
1 stop22h 11mSun Country Air
Deal found 10/29$385
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:20 pmHRL - ORD
2 stops14h 45mUnited Airlines
Sat 1/37:35 amORD - HRL
1 stop8h 31mUnited Airlines
Deal found 10/29$391

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 October 30, 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

Thu 12/25

11:49 am-4:42 pm

1 stop28h 53m

Chicago O'Hare Intl

Thu 1/1

6:14 pm-10:53 am

1 stop16h 39m

$274

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 12/26

12:37 pm-6:44 pm

1 stop6h 07m

Chicago O'Hare Intl

Tue 12/30

6:44 pm-10:53 am

1 stop16h 09m

$315

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 2/24

2:46 pm-10:26 pm

1 stop7h 40m

Chicago O'Hare Intl

Wed 2/25

2:55 pm-10:51 pm

1 stop7h 56m

$331

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 11/13

5:40 am-11:47 am

1 stop6h 07m

Chicago O'Hare Intl

Mon 11/17

5:10 pm-11:14 pm

1 stop6h 04m

$359

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 11/11

4:02 pm-10:20 pm

1 stop6h 18m

Chicago O'Hare Intl

Sat 11/15

10:25 am-6:10 pm

1 stop7h 45m

$374

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 12/22

11:43 am-10:26 am

1 stop22h 43m

Chicago O'Hare Intl

Fri 1/2

11:51 am-10:02 am

1 stop22h 11m

$385

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 12/22

5:20 pm-8:05 am

2 stops14h 45m

Chicago O'Hare Intl

Sat 1/3

7:35 am-4:06 pm

1 stop8h 31m

$391

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 12/3

5:00 pm-12:15 am

1 stop7h 15m

Chicago O'Hare Intl

Wed 12/10

8:59 am-9:49 pm

2 stops12h 50m

$404

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 12/23

5:34 am-10:54 am

1 stop5h 20m

Chicago O'Hare Intl

Thu 1/1

7:36 am-2:18 pm

1 stop6h 42m

$408

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 12/23

5:20 pm-12:14 am

1 stop6h 54m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 17 results
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Compare providers for flights from Harlingen to Chicago

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 Harlingen to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Harlingen, Texas-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Harlingen, Texas-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Harlingen, Texas-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Harlingen, Texas-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Harlingen, Texas-Chicago 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 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, December is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $130). Flying from Harlingen, Texas to Chicago in February is currently the most expensive (average of $328). 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 October 30, 2025.

It’s optimal to fly from Harlingen, Texas to Chicago in the morning. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the afternoon.

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 October 30, 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
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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?

    Sun Country Air and American Airlines can get you from Harlingen, Texas to Chicago in just under 6h 07m. Your travel time can differ by up to 1h 33m. 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 32% 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 United Airlines. According to our data, you can fly for as low as $140. Users have also found prices from $168 and $306 on Sun Country Air and Southwest, 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, December is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $130). Flying from Harlingen, Texas to Chicago in February is currently the most expensive (average of $328). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$407FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$252Average$319FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$288Average$397FlexibilityNo cancel feeOn-time69%

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