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 $269 on this airline. Additional options worth looking into are Delta and Southwest, starting at $279 and $343 round-trip. American Airlines is priced at 20% 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 American Airlines. According to our data, you can fly for as low as $135. Users have also found prices from $145 and $235 on Delta and United Airlines, respectively.

What is the cheapest day to fly from Harlingen, Texas to Chicago?

Travelers seeking maximum savings on their Harlingen, Texas to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Harlingen, Texas to Chicago?

Looking at all options, your cheapest flight can be booked for $268. While the most popular route (Harlingen Valley Intl - Chicago O'Hare Intl) can be booked for $278 on average our data indicates $531 when flying from Harlingen, Texas to Chicago.

What is the cheapest day to fly round-trip from Harlingen, Texas to Chicago?

Flights from Harlingen, Texas to Chicago are found to be more expensive on Friday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

What is the cheapest month to fly from Harlingen, Texas to Chicago?

May is one of the best times of the year to fly to Chicago from Harlingen, Texas. Prices for May average $340 per person but you can even find prices for as low as $227. The most expensive prices can be found in the month of July. Opting for a May flight can save you 38% on your journey compared to booking in July

Most accurate provider : When it comes to deals on Harlingen, Texas-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Harlingen, Texas-Chicago flight deals on Cheapflights vs. FlightHub >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 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 Harlingen, Texas-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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. 2 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.

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.

$135+ Flights from Harlingen, TX to Chicago

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Cheap flight deals from Harlingen to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$269 (American Airlines)
One-way from	$135 (American Airlines)
Popular in	July
Cheapest in	May
Average price	$332
Good round-trip deal	$531 or less

Provider with most accurate pricing for Harlingen Valley Intl-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Harlingen Valley Intl-Chicago (CHI) flights.

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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. 15% potential increase in price ($63 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 March 2025

Search Deals

Price to beat on a round-trip flight from Harlingen Valley Intl to Chicago (CHI).

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 March 28, 2025.

Sat 6/288:10 pmHRL - ORD

1 stop4h 49mAmerican Airlines

Sat 7/55:00 amORD - HRL

1 stop4h 37mAmerican Airlines

Deal found 3/28

$269

Fri 4/112:40 pmHRL - ORD

1 stop7h 05mDelta

Tue 4/156:35 amORD - HRL

1 stop7h 11mDelta

Deal found 3/27

$279

Mon 5/197:00 amHRL - ORD

1 stop9h 25mSouthwest

Sun 5/257:30 amORD - HRL

2 stops13h 35mSouthwest

Deal found 3/27

$343

Thu 10/25:16 pmHRL - ORD

1 stop6h 54mUnited Airlines

Sun 10/57:45 amORD - HRL

1 stop7h 49mUnited Airlines

Deal found 3/27

$349

Tue 4/11:45 pmHRL - ORD

3 stops35h 53mMultiple Airlines

Tue 4/89:57 pmORD - HRL

3 stops36h 48mMultiple Airlines

Deal found 3/27

$743

Best flights from Harlingen to Chicago
Discover carefully curated flight deals from Harlingen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 28, 2025.

Sat 6/288:10 pmHRL - ORD

1 stop4h 49mAmerican Airlines

Sat 7/55:00 amORD - HRL

1 stop4h 37mAmerican Airlines

Deal found 3/28

$269

Fri 4/112:40 pmHRL - ORD

1 stop7h 05mDelta

Tue 4/156:35 amORD - HRL

1 stop7h 11mDelta

Deal found 3/27

$279

Mon 5/197:00 amHRL - ORD

1 stop9h 25mSouthwest

Sun 5/257:30 amORD - HRL

2 stops13h 35mSouthwest

Deal found 3/27

$343

Thu 5/225:20 pmHRL - ORD

1 stop6h 53mUnited Airlines

Mon 5/266:00 amORD - HRL

1 stop7h 25mUnited Airlines

Deal found 3/27

$419

Last-minute flights from Harlingen to Chicago
Discover last-minute flight deals from Harlingen to Chicago. Data last updated March 28, 2025 and is based on user searches.

Tue 4/14:32 pmHRL - ORD

1 stop7h 46mAmerican Airlines

Tue 4/86:00 amORD - HRL

1 stop5h 30mAmerican Airlines

Deal found 3/27

$409

Tue 4/16:15 amHRL - ORD

2 stops10h 30mSouthwest

Tue 4/81:30 pmORD - HRL

2 stops9h 30mSouthwest

Deal found 3/27

$419

Tue 4/11:45 pmHRL - ORD

3 stops35h 53mMultiple Airlines

Tue 4/89:57 pmORD - HRL

3 stops36h 48mMultiple Airlines

Deal found 3/27

$743

Wed 4/22:34 pmHRL - ORD

1 stop7h 13mDelta

Sun 4/66:15 amORD - HRL

1 stop7h 30mDelta

Deal found 3/27

$409

Wed 4/25:15 amHRL - ORD

2 stops13h 00mUnited Airlines

Sun 4/67:45 amORD - HRL

1 stop5h 43mUnited Airlines

Deal found 3/27

$675

Wed 4/25:46 amHRL - ORD

2 stops6h 54mAmerican Airlines

Sun 4/64:40 pmORD - HRL

2 stops7h 19mAmerican Airlines

Deal found 3/27

$1,016

Fri 4/112:40 pmHRL - ORD

1 stop7h 05mDelta

Tue 4/156:35 amORD - HRL

1 stop7h 11mDelta

Deal found 3/27

$279

Fri 4/112:05 pmHRL - ORD

1 stop7h 23mUnited Airlines

Tue 4/157:10 amORD - HRL

2 stops12h 34mUnited Airlines

Deal found 3/27

$441

One-way flights from Harlingen to Chicago
Search for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated March 28, 2025.

Tue 7/15:25 amHRL - ORD

1 stop5h 30mAmerican Airlines

Deal found 3/27

$135

Sat 4/121:05 pmHRL - ORD

2 stops10h 54mDelta

Deal found 3/27

$145

Mon 7/215:20 pmHRL - ORD

2 stops16h 18mUnited Airlines

Deal found 3/28

$235

Cheapflights Fare Finder

Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 6/28

8:10 pm-12:59 am

1 stop4h 49m

Chicago O'Hare Intl

Sat 7/5

5:00 am-9:37 am

1 stop4h 37m

$269

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 4/11

2:40 pm-9:45 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 4/15

6:35 am-1:46 pm

1 stop7h 11m

$279

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 5/19

7:00 am-4:25 pm

1 stop9h 25m

Chicago O'Hare Intl

Sun 5/25

7:30 am-9:05 pm

2 stops13h 35m

$343

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 5/22

5:20 pm-12:13 am

1 stop6h 53m

Chicago O'Hare Intl

Mon 5/26

6:00 am-1:25 pm

1 stop7h 25m

$419

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 7/1

5:25 am-10:55 am

1 stop5h 30m

$135

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 4/12

1:05 pm-11:59 pm

2 stops10h 54m

$145

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 7/21

5:20 pm-9:38 am

2 stops16h 18m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Compare providers for flights from Harlingen to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Harlingen to Chicago in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Harlingen, Texas-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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, 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 $323). 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?

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

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

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

See what other customers who have flown with Southwest, Delta and United 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

8.1

Very good

4,273 reviews

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

8.1

Very good

4,273 reviews

Southwest

8.1

Very good

4,273 reviews

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.

Delta

8.0

Very good

7,896 reviews

Southwest

8.1

Very good

4,273 reviews

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

8,603 reviews

Southwest

8.1

Very good

4,273 reviews

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

8.1

Very good

4,273 reviews

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

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. 2 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 $269 on this airline. Additional options worth looking into are Delta and Southwest, starting at $279 and $343 round-trip. American Airlines is priced at 20% 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 American Airlines. According to our data, you can fly for as low as $135. Users have also found prices from $145 and $235 on Delta and United Airlines, respectively.
What are the cheapest flights from Harlingen, Texas to Chicago?
Looking at all options, your cheapest flight can be booked for $268. While the most popular route (Harlingen Valley Intl - Chicago O'Hare Intl) can be booked for $278 on average our data indicates $531 when flying from Harlingen, Texas to Chicago.
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 $323). 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

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Porter

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Top 2 airlines flying from Harlingen to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$233	Average$358	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$281	Average$414	FlexibilityNo cancel fee	On-time69%

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$135+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Harlingen to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Harlingen to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Harlingen to Chicago

Cheapest flights from Harlingen to ChicagoExplore 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 March 28, 2025.

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 March 28, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.

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 March.

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.

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?

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 March 28, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

See what other customers who have flown with Southwest, Delta and United 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.

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?

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

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

What are the cheapest flights from Harlingen, Texas to Chicago?

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

How can I find direct flights from Harlingen to Chicago?

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

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

Traveling to a place near Harlingen?

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Alternative routes for Harlingen to Chicago

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Top 2 airlines flying from Harlingen to Chicago

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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 March 28, 2025.