HRL - MDW

$166 Find Cheap Flights from Harlingen to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$248
Typical prices: $318-$485
Southwest
Mon 12/10Fri 12/14
HRL - MDW • 1 stop
Cheapest one-way
$166
Typical prices: $217-$234
Southwest
Sun 11/18
HRL - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Harlingen and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
November
Cheapest • 12% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Austin Bergstrom (AUS)
Cheapest • Avg $354 (round-trip)
Houston Hobby (HOU)
Shortest trip • 5h 25m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
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Booking Insights
Flight Deals

Cheap Flights from Harlingen to Midway (HRL-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Harlingen to Midway

Thu, Dec 10 - Mon, Dec 14
Southwest Logo
4:30 pm - 11:10 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 40m1 stop Houston Hobby
Southwest Logo
10:55 am - 5:20 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
6h 25m1 stop Dallas Love Field
$248Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
4:30 pm - 11:10 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 40m1 stop Houston Hobby
Southwest Logo
9:40 am - 5:20 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
7h 40m2 stops Lambert-St Louis Dallas Love Field
$254Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
4:30 pm - 10:40 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 10m2 stops Houston Hobby Dallas Love Field
Southwest Logo
9:40 am - 5:20 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
7h 40m2 stops Lambert-St Louis Dallas Love Field
$330Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
2:55 pm - 7:50 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
4h 55m1 stop Dallas Love Field
Southwest Logo
5:00 pm - 9:50 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
4h 50m1 stop Houston Hobby
$331Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
12:45 pm - 7:50 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
7h 05m2 stops Houston Hobby Dallas Love Field
Southwest Logo
5:00 pm - 9:50 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
4h 50m1 stop Houston Hobby
$336Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
12:45 pm - 7:50 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
7h 05m2 stops Houston Hobby Dallas Love Field
Southwest Logo
7:05 am - 3:50 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
8h 45m2 stops Dallas Love Field Houston Hobby
$341Southwest
Tue, Dec 15 - Tue, Dec 22
Southwest Logo
11:35 am - 7:55 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
8h 20m1 stop Dallas Love Field
Southwest Logo
1:40 pm - 12:10 amMDW  Chicago Midway-HRL Harlingen Valley Intl
10h 30m1 stop Houston Hobby
$391Southwest
Tue, Dec 15 - Tue, Dec 22
Southwest Logo
4:30 pm - 10:40 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 10m2 stops Houston Hobby Dallas Love Field
Southwest Logo
1:40 pm - 12:10 amMDW  Chicago Midway-HRL Harlingen Valley Intl
10h 30m1 stop Houston Hobby
$391Southwest
Tue, Dec 15 - Tue, Dec 22
Southwest Logo
4:30 pm - 10:40 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 10m2 stops Houston Hobby Dallas Love Field
Southwest Logo
3:40 pm - 12:10 amMDW  Chicago Midway-HRL Harlingen Valley Intl
8h 30m2 stops Dallas Love Field Houston Hobby
$405Southwest
Tue, Nov 3 - Sat, Nov 7
Southwest Logo
4:30 pm - 11:05 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
6h 35m1 stop Houston Hobby
Southwest Logo
7:35 am - 12:05 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
4h 30m1 stop Houston Hobby
$419Southwest
Booking Insights

Price, demand and travel trends for Harlingen to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Harlingen to Chicago Midway Airport?

Round-trip flights from Harlingen to Chicago Midway Airport typically range from $318 to $485. The lowest price found in the past 5 days was $248, on Southwest.

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Key details for Harlingen to Chicago Midway Airport flights

Low season

January

Cheapest flight

$166
Beat the crowds with an average 80% drop in travelers.
The most popular month to fly with an average 27% increase in travelers.
One-way flight from Harlingen to Chicago Midway Airport

When to book flights from Harlingen to Midway

Are your dates flexible? Find out the best times to travel from Harlingen to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Harlingen to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Harlingen to Chicago Midway Airport?

    Only Economy Class is available on flights from Harlingen to Chicago Midway Airport.

  • How long is a flight from Harlingen to Chicago Midway Airport?

    A nonstop flight from Harlingen to Chicago Midway Airport takes 00m, covering 1,213 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Harlingen to Chicago Midway Airport flight?

    Round-trip flights from Harlingen to Chicago Midway Airport range from $318 to $485, with an average of $363 over the past 12 months. Anything below $318 counts as a good deal.

  • Have flight prices from Harlingen to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $248 to $771. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Harlingen to Chicago Midway Airport looking right now?

    One-way fares from Harlingen to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $172, which is 23% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Harlingen to Chicago Midway Airport?

    Flights from Harlingen to Chicago Midway Airport usually depart from Harlingen Valley Intl (HRL) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Harlingen to Chicago Midway Airport pass through?

    One-stop flights from Harlingen to Chicago Midway Airport most commonly connect through:

    • Houston Hobby (HOU) - 68% of one-stop connections
    • Austin Bergstrom (AUS) - 27% of one-stop connections
    • Dallas Love Field (DAL) - 5% of one-stop connections

  • Can I save money by using flexible dates for flights from Harlingen to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 36% on flights from Harlingen to Chicago Midway Airport. Tuesday is the cheapest departure day at $333 round-trip on average, while Friday is the most expensive at $513, a difference of $180.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Harlingen to Chicago Midway Airport?

    Flying via Austin Bergstrom (AUS) gives the shortest average 1-stop total travel time at 5h 22m, compared with 5h 25m via Houston Hobby (HOU) and 5h 27m via Dallas Love Field (DAL).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Harlingen to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Friday. On this route, Tuesday flights average $333, about $180 less than Friday fares (35% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Harlingen to Chicago Midway Airport trip for November. Fares historically average $318 round-trip in that month - typically $190 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Harlingen to Midway

Complete your trip to Chicago with a hotel stay or car rental

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