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 $251 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $260 and $319 round-trip. American Airlines is priced at 22% 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 $126. Users have also found prices from $145 and $180 on Southwest 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 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 $326 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 40% 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 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.

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.

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.

$126+ Flights from Harlingen, TX to Chicago

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1. Tell us where you want to go

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Cheap flight deals from Harlingen to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$251 (American Airlines)
One-way from	$126 (American Airlines)
Popular in	July
Cheapest in	May
Average price	$233

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)

Search Deals

Highest demand for flights based on searches. 14% potential increase in price ($56 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in May 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 mayo 1, 2025.

vie. 5/1612:05 pmHRL - ORD

1 stop7h 35mAmerican Airlines

sáb. 5/2412:09 pmORD - HRL

1 stop7h 17mAmerican Airlines

Deal found 4/29

$244

mié. 5/145:30 pmHRL - ORD

1 stop5h 28mUnited Airlines

dom. 5/187:35 amORD - HRL

1 stop5h 49mUnited Airlines

Deal found 4/29

$279

jue. 7/107:00 amHRL - ORD

1 stop5h 45mSouthwest

jue. 7/174:20 pmORD - HRL

1 stop5h 25mSouthwest

Deal found 4/29

$299

mar. 12/163:00 pmHRL - ORD

1 stop6h 52mDelta

sáb. 12/206:20 amORD - HRL

1 stop8h 16mDelta

Deal found 4/29

$674

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 mayo 1, 2025.

sáb. 6/148:10 pmHRL - ORD

1 stop4h 49mAmerican Airlines

sáb. 6/211:28 pmORD - HRL

1 stop6h 12mAmerican Airlines

Deal found 4/30

$251

mié. 6/45:20 pmHRL - ORD

1 stop5h 52mUnited Airlines

dom. 6/86:00 amORD - HRL

1 stop7h 25mUnited Airlines

Deal found 4/30

$260

mié. 7/96:00 amHRL - ORD

2 stops9h 00mSouthwest

vie. 7/184:20 pmORD - HRL

1 stop5h 25mSouthwest

Deal found 4/30

$319

Last-minute flights from Harlingen to Chicago
Discover last-minute flight deals from Harlingen to Chicago. Data last updated mayo 1, 2025 and is based on user searches.

mié. 5/145:30 pmHRL - ORD

1 stop5h 28mUnited Airlines

dom. 5/187:35 amORD - HRL

1 stop5h 49mUnited Airlines

Deal found 4/29

$279

vie. 5/1612:05 pmHRL - ORD

1 stop7h 35mAmerican Airlines

sáb. 5/2412:09 pmORD - HRL

1 stop7h 17mAmerican Airlines

Deal found 4/29

$244

jue. 5/297:00 amHRL - ORD

2 stops8h 00mSouthwest

mar. 6/37:30 amORD - HRL

1 stop9h 10mSouthwest

Deal found 4/30

$365

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 mayo 1, 2025.

mié. 5/2110:15 amHRL - ORD

1 stop5h 14mAmerican Airlines

Deal found 4/29

$126

mié. 5/147:30 amHRL - ORD

1 stop8h 55mSouthwest

Deal found 4/29

$145

mié. 5/145:30 pmHRL - ORD

1 stop6h 45mUnited Airlines

Deal found 4/30

$180

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

vie. 5/16

12:05 pm-7:40 pm

1 stop7h 35m

Chicago O'Hare Intl

sáb. 5/24

12:09 pm-7:26 pm

1 stop7h 17m

$244

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

mié. 5/14

5:30 pm-10:58 pm

1 stop5h 28m

Chicago O'Hare Intl

dom. 5/18

7:35 am-1:24 pm

1 stop5h 49m

$279

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

jue. 7/10

7:00 am-12:45 pm

1 stop5h 45m

Chicago O'Hare Intl

jue. 7/17

4:20 pm-9:45 pm

1 stop5h 25m

$299

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

mié. 5/21

10:15 am-3:29 pm

1 stop5h 14m

$126

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

mié. 5/14

7:30 am-4:25 pm

1 stop8h 55m

$145

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

mié. 5/14

5:30 pm-12:15 am

1 stop6h 45m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 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 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, 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?

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

Southwest

8.0

Very good

4,294 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

8.0

Very good

4,294 reviews

Southwest

8.0

Very good

4,294 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

8,696 reviews

Southwest

8.0

Very good

4,294 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

8.0

Very good

4,294 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. 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 $251 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $260 and $319 round-trip. American Airlines is priced at 22% 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 $126. Users have also found prices from $145 and $180 on Southwest 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.

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Top 3 airlines flying from Harlingen to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$236	Average$358	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$263	Average$307	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$288	Average$414	FlexibilityNo cancel fee	On-time69%

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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 5/21. 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

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 mayo 1, 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 mayo 1, 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 May.

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 mayo 1, 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

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?

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 3 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 mayo 1, 2025.