$86 Cheap Flights from Harlingen (HRL) to Chicago (MDW)

View $86 flight on Wed, Oct 15, 2025Opens in a new window

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

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Cheap Flights from Harlingen to Chicago (HRL-MDW)

Prices were available within the past 7 days and start at $86 for one-way flights and $171 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 1 - Tue, Oct 21
HRL
Harlingen
MDW
Chicago
$171 Roundtrip, found 10 hours ago
$171
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Harlingen to Chicago, returning Tue, Oct 21, priced at $171 found 10 hours ago
Southwest Airlines
Tue, Sep 2 - Tue, Sep 9
HRL
Harlingen
MDW
Chicago
$176 Roundtrip, found 4 hours ago
$176
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Harlingen to Chicago, returning Tue, Sep 9, priced at $176 found 4 hours ago
Southwest Airlines
Tue, Oct 14 - Wed, Oct 15
HRL
Harlingen
MDW
Chicago
$191 Roundtrip, found 8 hours ago
$191
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Harlingen to Chicago, returning Wed, Oct 15, priced at $191 found 8 hours ago
Southwest Airlines
Tue, Sep 2 - Tue, Sep 9
HRL
Harlingen
MDW
Chicago
$196 Roundtrip, found 4 hours ago
$196
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Harlingen to Chicago, returning Tue, Sep 9, priced at $196 found 4 hours ago
Southwest Airlines
Wed, Oct 1 - Tue, Oct 21
HRL
Harlingen
MDW
Chicago
$200 Roundtrip, found 10 hours ago
$200
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Harlingen to Chicago, returning Tue, Oct 21, priced at $200 found 10 hours ago
Southwest Airlines
Wed, Oct 1 - Tue, Oct 21
HRL
Harlingen
MDW
Chicago
$205 Roundtrip, found 10 hours ago
$205
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Harlingen to Chicago, returning Tue, Oct 21, priced at $205 found 10 hours ago
Southwest Airlines
Thu, Oct 2 - Mon, Oct 6
HRL
Harlingen
MDW
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Harlingen to Chicago, returning Mon, Oct 6, priced at $209 found 1 day ago
Southwest Airlines
Tue, Sep 2 - Tue, Sep 9
HRL
Harlingen
MDW
Chicago
$211 Roundtrip, found 4 hours ago
$211
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Harlingen to Chicago, returning Tue, Sep 9, priced at $211 found 4 hours ago
Southwest Airlines
Thu, Oct 2 - Mon, Oct 6
HRL
Harlingen
MDW
Chicago
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Harlingen to Chicago, returning Mon, Oct 6, priced at $214 found 1 day ago
Delta
Mon, Oct 6 - Sat, Oct 25
HRL
Harlingen
MDW
Chicago
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 6 from Harlingen to Chicago, returning Sat, Oct 25, priced at $243 found 1 day ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $365
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $365
Flights from Harlingen (HRL) to Chicago (MDW)
Origin airport
Valley Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$170
Distance
1214 mi

Harlingen to Chicago Flights

The cheapest times to fly from Harlingen to Chicago

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 Harlingen to Chicago are during the month of October. You can find some of the cheapest flights from Harlingen to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Harlingen to Chicago

Sunday is one of the best days to book for cheap flights from Harlingen to Chicago: 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 Harlingen to Chicago

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 Harlingen to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $86 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 Harlingen to Chicago 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 Harlingen to Chicago 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.

 

Frequently asked questions

How much does a flight from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $86 or cheap return flight from $171 from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW)?
Planning your trip for October may help you find better deals, as it's the cheapest month for flights between HRL and MDW. You'll usually find the lowest prices during off-peak months.
What is the cheapest airline that flies from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest HRL to MDW flight.
How many flights per day from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW)?
Nonstop flights from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from HRL to MDW?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary based on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW)?
Select a flight from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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 Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a ticket from HRL to MDW often results in higher prices. While it's possible to find some last-minute discounts, there's no guarantee. Keep your travel plans flexible to maximize your chances of snagging a bargain.
Is it cheaper to book a HRL to MDW flight and hotel package?
You'll typically save money by securing a HRL to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After selecting your ideal accommodations and flights, you can add extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Valley Intl. Airport (HRL) to Midway Intl. Airport (MDW)?
Typically, you're able to cancel or reschedule your HRL to MDW flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you'd like more information, head to our Customer Service portal.

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*Available to One Key members.