HRL - CHI

$153 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
$311
Typical prices: $315-$465
American Airlines
Wed 10/17Sun 10/21
HRL - ORD • 1 stop
Cheapest one-way
$153
Typical prices: $180-$299
Sun Country Air
Mon 11/12
HRL - ORD • 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.
Insights
Insights
Top routes
HRL - MDW
Cheapest • 6% average savings
HRL - ORD
Most popular
Insights
Insights
When to travel
May
Cheapest • 20% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $361 (round-trip)
Dallas Love Field (DAL)
Shortest trip • 5h 27m (one-way)
Insights
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, Oct 17 - Wed, Oct 21
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:08 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 08m1 stop Dallas/Fort Worth
$311American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:08 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 08m1 stop Dallas/Fort Worth
$325American Airlines
Fri, Oct 30 - Tue, Nov 3
American Airlines Logo
10:40 am - 4:16 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 36m1 stop Dallas/Fort Worth
American Airlines Logo
3:00 pm - 11:31 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
8h 31m1 stop Dallas/Fort Worth
$325American Airlines
Fri, Oct 16 - Wed, Oct 21
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:08 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 08m1 stop Dallas/Fort Worth
$325American Airlines
Fri, Oct 16 - Mon, Oct 19
Delta Logo
2:13 pm - 7:38 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 25m1 stop Minneapolis St Paul
Delta Logo
6:20 am - 1:23 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 03m1 stop Minneapolis St Paul
$354Delta
Fri, Dec 25 - Thu, Dec 31
Sun Country Air Logo
12:34 pm - 6:45 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 11m1 stop Minneapolis St Paul
Sun Country Air Logo
11:53 am - 10:49 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
22h 56m1 stop Minneapolis St Paul
$365Sun Country Air
Thu, Dec 24 - Thu, Dec 31
Sun Country Air Logo
11:46 am - 10:23 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
22h 37m1 stop Minneapolis St Paul
Sun Country Air Logo
11:53 am - 10:49 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
22h 56m1 stop Minneapolis St Paul
$365Sun Country Air
Wed, Oct 21 - Sun, Oct 25
United Airlines Logo
5:05 am - 11:16 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 11m1 stop Houston George Bush Intcntl
United Airlines Logo
5:30 am - 10:50 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 20m1 stop Houston George Bush Intcntl
$370United Airlines
Thu, Sep 24 - Sat, Sep 26
United Airlines Logo
5:05 am - 10:16 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 11m1 stop Houston George Bush Intcntl
United Airlines Logo
8:45 am - 3:59 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 14m1 stop Houston George Bush Intcntl
$389United Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
5:18 pm - 11:26 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 08m1 stop Houston George Bush Intcntl
United Airlines Logo
4:11 pm - 9:52 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 41m1 stop Houston George Bush Intcntl
$394United Airlines
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 from Harlingen to Chicago with more confidence.

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

Round-trip flights from Harlingen to Chicago start at $311. Prices are below average for this route right now, with typical round-trip fares ranging from $315 to $465. The lowest price found in the past 5 days was $311 on American Airlines.

What is the cheapest Harlingen to Chicago flight route?

Harlingen (HRL) to Chicago Midway Airport (MDW) is the cheapest Harlingen to Chicago route, averaging $338 round-trip. Other Harlingen to Chicago routes average $384, based on KAYAK data over the past 12 months.

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

Saturday is the cheapest day of the week to fly from Harlingen to Chicago, it is 10% cheaper than the average day. Monday is the most expensive day with flight prices 28% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is 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 March ($453) 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

$153
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Harlingen to Chicago O'Hare Intl 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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

  • 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

  • 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) - 35% of one-stop connections
    • Dallas/Fort Worth (DFW) - 31% of one-stop connections
    • Austin Bergstrom (AUS) - 20% of one-stop connections
    • Houston Hobby (HOU) - 12% of one-stop connections

    Houston George Bush Intcntl (IAH) handles the largest share of one-stop connections on this route.

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

    On the Harlingen to Chicago route, being flexible with your departure day can save you up to 30%. Saturday is the cheapest day at $336 round-trip on average, while Monday is the most expensive at $476: a $140 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What popular places can I visit in Chicago?

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

  • How long is a flight from Harlingen to Chicago?

    A nonstop flight from Harlingen to Chicago takes 0h 00m, 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.

  • 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 $311 to $1,111. That means the highest observed fare was about 4x 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 lower than usual. Average one-way flight prices are about $156, which is 33% below the typical average for this route.

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

    Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 5h 27m, compared with 5h 32m via Houston George Bush Intcntl (IAH) and 5h 50m via Dallas/Fort Worth (DFW).

  • 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 from around $17:

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

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

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

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

    Round-trip flights from Harlingen to Chicago range from $315 to $465, with an average of $371 over the past 12 months. Anything below $315 counts as a good deal.

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 can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $336 - about $140 less than Monday (29% 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

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