$109 Cheap Flights from Chicago (MDW) to Harlingen (HRL)

View $109 flight on Wed, Feb 18, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Valley Intl. Airport (HRL)

Cheap Flights from Chicago to Harlingen (MDW-HRL)

Prices were available within the past 7 days and start at $109 for one-way flights and $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
HRL
Harlingen
$245 Roundtrip, found 23 hours ago
$245
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Wed, Dec 10, priced at $245 found 23 hours ago
Southwest Airlines
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
HRL
Harlingen
$248 Roundtrip, found 23 hours ago
$248
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Wed, Dec 10, priced at $248 found 23 hours ago
Southwest Airlines
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
HRL
Harlingen
$251 Roundtrip, found 23 hours ago
$251
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Wed, Dec 10, priced at $251 found 23 hours ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
HRL
Harlingen
$257 Roundtrip, found 17 hours ago
$257
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Mon, Dec 8, priced at $257 found 17 hours ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
HRL
Harlingen
$260 Roundtrip, found 17 hours ago
$260
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Mon, Dec 8, priced at $260 found 17 hours ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
HRL
Harlingen
$262 Roundtrip, found 17 hours ago
$262
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Mon, Dec 8, priced at $262 found 17 hours ago
Southwest Airlines
Wed, Feb 18 - Mon, Feb 23
MDW
Chicago
HRL
Harlingen
$263 Roundtrip, found 6 days ago
$263
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Chicago to Harlingen, returning Mon, Feb 23, priced at $263 found 6 days ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
HRL
Harlingen
$265 Roundtrip, found 17 hours ago
$265
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Mon, Dec 8, priced at $265 found 17 hours ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
HRL
Harlingen
$267 Roundtrip, found 17 hours ago
$267
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Harlingen, returning Mon, Dec 8, priced at $267 found 17 hours ago
Delta
Wed, Dec 31 - Fri, Jan 16
MDW
Chicago
HRL
Harlingen
$376 Roundtrip, found 6 days ago
$376
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 31 from Chicago to Harlingen, returning Fri, Jan 16, priced at $376 found 6 days ago

Find the cheapest month to fly from Chicago (MDW) to Harlingen (HRL)

September is typically the cheapest month to fly

From $208 - $1,035 per traveler.

Alternative airports near Harlingen

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Valley Intl. HRL. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $339
HRL
Valley Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $339

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL) cost?
Get a cheap one-way flight from $109 or cheap return flight from $245 from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL)?
December is the cheapest month to fly from MDW to HRL. Traveling during quieter months is often the key to finding a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from MDW to HRL. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from MDW to HRL?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change based on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL) route, aim to fly before 3 PM. Flights after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL) last-minute?
Booking your plane ticket from MDW to HRL just before your journey is usually more expensive. However, if you're flexible with your schedule, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to HRL flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to HRL flight and hotel package with Expedia could result in significant savings. Better still, having it all in one place takes the hassle out of travel planning. Just pick your flights and select from our wide range of hotels, then customize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Valley Intl. Airport (HRL)?
You can usually reschedule or cancel your MDW to HRL flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Valley Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$245
Distance
1214 mi

Book with confidence

Chicago to Harlingen Flights

The cheapest times to fly from Chicago to Harlingen

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Harlingen are during the month of December. You can find some of the cheapest flights from Chicago to Harlingen with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Harlingen

Sunday is one of the best days to book for cheap flights from Chicago to Harlingen: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Harlingen

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Harlingen in 2025. You can also book with separate airlines for your outbound and return journeys, from $109 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Harlingen flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Harlingen airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Harlingen Flights

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*Available to One Key members.