HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$93+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Harlingen to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 24, 2026.

This Southwest deal was found by Cheapflights users on 3/22. 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.
Mon 5/46:55 am
HRL
-
ORD
1 stop6h 20m
Southwest
Wed 5/63:45 pm
ORD
-
HRL
1 stop5h 10m
Southwest
Deal found 3/22$203
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Sat 8/225:16 pm
HRL
-
ORD
1 stop6h 01m
United Airlines
Sat 8/2910:32 am
ORD
-
HRL
1 stop5h 02m
United Airlines
Deal found 3/20$277
This Southwest deal was found by Cheapflights users on 3/20. 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.
Thu 4/306:55 am
HRL
-
ORD
1 stop6h 20m
Southwest
Fri 5/14:15 pm
ORD
-
HRL
2 stops6h 45m
Southwest
Deal found 3/20$282
This Southwest deal was found by Cheapflights users on 3/18. 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 5/207:10 am
HRL
-
ORD
1 stop6h 05m
Southwest
Sun 5/242:40 pm
ORD
-
HRL
2 stops7h 20m
Southwest
Deal found 3/18$322
This Southwest deal was found by Cheapflights users on 3/19. 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 4/17:00 am
HRL
-
ORD
1 stop6h 15m
Southwest
Sun 4/53:45 pm
ORD
-
HRL
1 stop6h 15m
Southwest
Deal found 3/19$337
This Southwest deal was found by Cheapflights users on 3/19. 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 4/17:00 am
HRL
-
ORD
1 stop6h 15m
Southwest
Mon 4/62:40 pm
ORD
-
HRL
2 stops9h 25m
Southwest
Deal found 3/19$342
This American Airlines deal was found by Cheapflights users on 3/21. 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 5/264:57 pm
HRL
-
ORD
1 stop7h 45m
American Airlines
Sat 5/306:32 pm
ORD
-
HRL
1 stop5h 42m
American Airlines
Deal found 3/21$348
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Sat 5/25:18 pm
HRL
-
ORD
1 stop5h 56m
United Airlines
Tue 5/52:10 pm
ORD
-
HRL
1 stop7h 49m
United Airlines
Deal found 3/19$367

Find 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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Southwest)

One-way from

$93
(Southwest)

Popular in

January

Cheapest in

May

Average price

$453
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.
Search Deals
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. 13% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 24, 2026.
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

Cheapest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 5/4

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 5/6

3:45 pm-8:55 pm

1 stop5h 10m

$203
Quickest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 4/30

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Fri 5/1

3:45 pm-8:35 pm

1 stop4h 50m

$277

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 5/9

12:10 pm-8:12 pm

1 stop8h 02m

Chicago O'Hare Intl

Tue 5/12

2:10 pm-8:00 pm

1 stop5h 50m

$308

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 5/2

5:18 pm-11:14 pm

1 stop5h 56m

Chicago O'Hare Intl

Tue 5/5

2:10 pm-9:59 pm

1 stop7h 49m

$367

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 8/21

5:16 pm-11:17 pm

1 stop6h 01m

Chicago O'Hare Intl

Fri 8/28

5:30 am-1:14 pm

1 stop7h 44m

$367

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 4/4

6:10 am-12:50 pm

2 stops6h 40m

Chicago O'Hare Intl

Tue 4/7

3:45 pm-8:55 pm

1 stop5h 10m

$383

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 6/13

5:20 pm-11:14 pm

1 stop5h 54m

Chicago O'Hare Intl

Wed 6/17

8:51 am-3:59 pm

1 stop7h 08m

$391

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 4/4

5:18 pm-12:45 am

1 stop7h 27m

Chicago O'Hare Intl

Wed 4/8

2:05 pm-7:40 pm

1 stop5h 35m

$433
Cheapest one-way

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 4/15

7:10 am-1:15 pm

1 stop6h 05m

$93

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 4/21

2:47 pm-10:45 pm

1 stop7h 58m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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, December is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $136). Flying from Harlingen, Texas to Chicago in February is currently the most expensive (average of $538). 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.

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 March 24, 2026.
Read through reviews of airlines operating flights from Harlingen to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
United Airlines
7.4
Good
9,469 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
American Airlines
7.1
Good
11,491 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 United Airlines can get you from Harlingen, Texas to Chicago in just under 5h 56m. Your travel time can differ by up to 24m. 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 United Airlines. Our recent data shows that you can find tickets from as low as $250 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $252 and $259 round-trip. United Airlines is priced at 25% 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, December is the cheapest month in which you can book a flight from Harlingen, Texas to Chicago (average of $136). Flying from Harlingen, Texas to Chicago in February is currently the most expensive (average of $538). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Harlingen to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Austin to O'Hare Intl flights
Love Field to O'Hare Intl flights
Austin to Midway flights
Love Field to Midway flights
San Antonio to O'Hare Intl flights
Hobby to Midway flights
Dallas/Fort Worth to St. Louis flights
George Bush Intcntl to Midway flights
Hobby to St. Louis flights
George Bush Intcntl to St. Louis flights
El Paso to O'Hare Intl flights
San Antonio to Midway flights
Austin to St. Louis flights
San Antonio to St. Louis flights
El Paso to Midway flights
Love Field to St. Louis flights
Dallas/Fort Worth to Bloomington flights
Dallas/Fort Worth to Peoria flights
Hobby to Peoria flights
El Paso to St. Louis flights
George Bush Intcntl to Peoria flights
McAllen to O'Hare Intl flights
Hobby to Bloomington flights
Austin to Moline flights
McAllen to Midway flights
Hobby to Moline flights
Laredo to O'Hare Intl flights
George Bush Intcntl to Moline flights
Harlingen to O'Hare Intl flights
George Bush Intcntl to Bloomington flights
Corpus Christi to O'Hare Intl flights
Lubbock to O'Hare Intl flights
Austin to Rockford flights
Dallas/Fort Worth to Moline flights
Hobby to Rockford flights
Austin to Bloomington flights
San Antonio to Moline flights
Dallas/Fort Worth to Evansville flights
Amarillo to O'Hare Intl flights
Midland to O'Hare Intl flights
Austin to Peoria flights
Dallas/Fort Worth to Champaign flights
Dallas/Fort Worth to Decatur flights

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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$250Average$408FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$252Average$319FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$259Average$435FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.