HRL - CHI

$149 Find Cheap Flights from Harlingen to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$345
Typical prices: $326-$478
American Airlines
Wed 12/5Fri 12/7
HRL - ORD • 1 stop
Cheapest one-way
$149
Typical prices: $182-$289
Southwest
Sat 11/24
HRL - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Harlingen and Chicago. You'll need to take a connecting flight to reach the destination.
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Top routes
HRL - MDW
Cheapest • 4% average savings
HRL - ORD
Most popular
Insights
Insights
When to travel
May
Cheapest • 23% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas Love Field (DAL)
Cheapest • Avg $388 (round-trip)
Houston Hobby (HOU)
Shortest trip • 5h 25m (one-way)
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Insights
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Flight Deals

Cheap Flights from Harlingen to Chicago (HRL-CHI)

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

Recent round-trip flight deals from Harlingen to Chicago

Sat, Dec 5 - Mon, Dec 7
American Airlines Logo
2:24 pm - 9:11 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 47m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:11 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 11m1 stop Dallas/Fort Worth
$345American Airlines
Thu, Dec 3 - Sat, Dec 5
American Airlines Logo
6:41 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 18m1 stop Dallas/Fort Worth
American Airlines Logo
3:04 pm - 11:26 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
8h 22m1 stop Dallas/Fort Worth
$345American Airlines
Mon, Dec 7 - Thu, Dec 17
United Airlines Logo
2:00 pm - 9:37 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
7h 37m1 stop Houston George Bush Intcntl
United Airlines Logo
7:00 am - 1:30 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 30m1 stop Houston George Bush Intcntl
$353United Airlines
Fri, Dec 11 - Sun, Dec 13
United Airlines Logo
4:39 pm - 10:56 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 17m1 stop Houston George Bush Intcntl
United Airlines Logo
7:30 am - 3:50 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
8h 20m1 stop Houston George Bush Intcntl
$359United Airlines
Thu, Dec 3 - Sun, Dec 6
American Airlines Logo
6:41 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 18m1 stop Dallas/Fort Worth
American Airlines Logo
6:59 am - 1:54 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 55m1 stop Dallas/Fort Worth
$359American Airlines
Sun, Jan 24 - Mon, Jan 25
United Airlines Logo
2:05 pm - 9:33 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
7h 28m1 stop Houston George Bush Intcntl
United Airlines Logo
7:25 am - 1:30 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 05m1 stop Houston George Bush Intcntl
$359United Airlines
Thu, Dec 10 - Sun, Dec 13
American Airlines Logo
2:24 pm - 10:15 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
7h 51m1 stop Dallas/Fort Worth
American Airlines Logo
4:00 pm - 10:54 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 54m1 stop Dallas/Fort Worth
$359American Airlines
Wed, Nov 25 - Wed, Dec 2
Southwest Logo
8:35 pm - 1:00 amHRL  Harlingen Valley Intl-MDW Chicago Midway
4h 25m1 stop Houston Hobby
Southwest Logo
3:55 pm - 8:45 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
4h 50m1 stop Austin Bergstrom
$363Southwest
Sun, Jan 24 - Mon, Jan 25
Southwest Logo
7:00 am - 3:10 pmHRL  Harlingen Valley Intl-MDW Chicago Midway
8h 10m2 stops Houston Hobby Dallas Love Field
Southwest Logo
3:45 pm - 9:05 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
5h 20m1 stop Austin Bergstrom
$364Southwest
Wed, Nov 25 - Wed, Dec 2
Southwest Logo
8:35 pm - 1:00 amHRL  Harlingen Valley Intl-MDW Chicago Midway
4h 25m1 stop Houston Hobby
Southwest Logo
7:35 am - 3:50 pmMDW  Chicago Midway-HRL Harlingen Valley Intl
8h 15m2 stops Lambert-St Louis Houston Hobby
$368Southwest
Booking Insights

Price, demand and travel trends for Harlingen to Chicago 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?

Round-trip flights from Harlingen to Chicago typically range from $326 to $478. The lowest price found in the past 5 days was $345, on American Airlines.

What is the cheapest Harlingen to Chicago flight route?

There's little price difference between Harlingen to Chicago routes. They average around $378 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Harlingen to Chicago?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Harlingen to Chicago. It’s 7% cheaper than the average day, while Friday is the most expensive, with prices 27% higher.

What’s the cheapest month to fly from Harlingen to Chicago?

•May is the cheapest month to fly from Harlingen to Chicago at $298 round-trip.
•June ($464) and October ($458) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 55% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Harlingen to Chicago flights

Low season

January

Cheapest flight

$149
Beat the crowds with an average 32% drop in travelers.
The most popular month to fly with an average 36% increase in travelers.
One-way flight from Harlingen to Chicago Midway Airport

When to book flights from Harlingen to Chicago

Are your dates flexible? Find out the best times to travel from Harlingen to Chicago 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 flight questions, answered

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

  • What are the earliest and latest flights from Harlingen to Chicago?

    These are the earliest and latest flight times available from Harlingen to Chicago:

    • Earliest: departs at 1:41 pm and lands at 4:59 pm
    • Latest: departs at 2:09 pm and lands at 5:27 pm.

    The flight takes about 3h 18m.

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

    Two cabin classes are available on flights from Harlingen to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Harlingen to Chicago?

    A nonstop flight from Harlingen to Chicago takes 3h 18m, covering 1,221 miles.

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

    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 flight?

    Round-trip flights from Harlingen to Chicago range from $326 to $478, with an average of $386 over the past 12 months. Anything below $326 counts as a good deal.

  • Have flight prices from Harlingen to Chicago 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 $345 to $840. That means the highest observed fare was about 2x higher than the lowest one.

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

    One-way fares from Harlingen to Chicago are currently in line with typical prices for this route. Average one-way fares are about $228.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

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

    Flights from Harlingen to Chicago usually depart from Harlingen Valley Intl (HRL) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

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

    • Houston George Bush Intcntl (IAH) - 36% of one-stop connections
    • Dallas/Fort Worth (DFW) - 34% of one-stop connections
    • Austin Bergstrom (AUS) - 17% of one-stop connections
    • Houston Hobby (HOU) - 12% of one-stop connections

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

    Yes. Flexible dates can save you up to 27% on flights from Harlingen to Chicago. Saturday is the cheapest departure day at $362 round-trip on average, while Friday is the most expensive at $494, a difference of $132.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Harlingen to Chicago?

    Only American Airlines operates flights between Harlingen and Chicago.

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

    Flying via Houston Hobby (HOU) gives the shortest average 1-stop total travel time at 5h 25m, compared with 5h 27m via Dallas Love Field (DAL) and 5h 32m via Houston George Bush Intcntl (IAH).

  • What popular places can I visit in Chicago?

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

Your guide to booking Harlingen to Chicago 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 Saturday departure and avoid flying on Friday. On this route, Saturday flights average $362, about $132 less than Friday fares (27% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Harlingen to Chicago trip for May. Fares historically average $298 round-trip in that month - typically $166 less than the most expensive month, which is June (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 Chicago Midway Airport

Prefer to fly direct from Harlingen to Chicago?

 
Find which airlines fly direct from Harlingen Valley Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Harlingen Valley Intl to Chicago

Saturday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago to Harlingen Valley Intl

Saturday

American Airlines

American Airlines

See more direct flights

More options for your flight from Harlingen to Chicago

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago