MDW - HRL

Find cheap flights from Chicago Midway Airport to Harlingen

1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Harlingen

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Harlingen, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Harlingen, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
Multiple Airlines
sáb. 1/31
MDW - HRL • multi-stop
Cheapest one-way
Multiple Airlines
sáb. 1/31
MDW - HRL • multi-stop
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Harlingen (MDW-HRL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Harlingen that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Harlingen

Multiple Airlines Logo
MDW
-
HRL
1213 mimulti-stop
Multiple Airlines Logo
HRL
-
MDW
1213 mimulti-stop
Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to Harlingen flights

Get data-powered insights and trends into flights from Midway to Harlingen to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Chicago Midway Airport to Harlingen?

Percentage of 1-stop round-trip flights from Chicago Midway Airport to Harlingen chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Houston (HOU) is the top choice – 69% of KAYAK users who clicked on 1-stop flights from Chicago Midway Airport to Harlingen picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago Midway Airport to Harlingen?

Average round-trip price for 1-stop flights from Chicago Midway Airport to Harlingen clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Dallas (DAL) offer the most affordable fares, with an average round-trip price of $337.

Which layover airport offers the shortest total travel time from Chicago Midway Airport to Harlingen?

Shortest average total travel time for 1-stop one-way flights from Chicago Midway Airport to Harlingen via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Dallas (DAL) for the shortest journey. The average one-way travel time for flights connecting there is 4h 35m.

Which layover airport has the quickest connection when flying from Chicago Midway Airport to Harlingen?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago Midway Airport to Harlingen, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Houston (HOU) often has the shortest layovers from Chicago Midway Airport to Harlingen, with an average of 1h 32m.

Find deals

Good to know

Low seasonOctober
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 3% increase in price.

When to book flights from Midway to Harlingen

Are your dates flexible? Find out the best times to travel from Midway to Harlingen based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Harlingen flights

  • Do I need a passport to fly between Chicago Midway Airport and Harlingen?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Harlingen?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Harlingen?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Harlingen.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Harlingen?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Harlingen from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Harlingen?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Harlingen with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and HRL can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Harlingen?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Harlingen from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Harlingen

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Harlingen. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Harlingen? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4267 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Everything you need to know for your flight from Midway to Harlingen

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Harlingen (HRL)