CHI - HRL

$165 Find Cheap Flights from Chicago to Harlingen - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Harlingen departing on 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$206
Overall average: $288
American Airlines
Tue 9/22Sat 9/26
ORD - HRL • 1 stop
Cheapest one-way
$165
Typical prices: $207-$280
American Airlines
Thu 7/9
ORD - HRL • 1 stop
Top airlines
Cheapest • from $206 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Harlingen. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $299 (round-trip)
Shortest trip • 5h 10m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 42% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Harlingen!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Harlingen (CHI-HRL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 Chicago to Harlingen

Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
5:00 am - 9:58 am
ORD
-
HRL
4h 58m
1 stop
American Airlines Logo
3:35 pm - 9:09 pm
HRL
-
ORD
5h 34m
1 stop
$206American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
5:00 am - 10:04 am
ORD
-
HRL
5h 04m
1 stop
American Airlines Logo
6:43 pm - 12:18 am
HRL
-
ORD
5h 35m
1 stop
$224American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
4:58 pm - 12:43 am
HRL
-
ORD
7h 45m
1 stop
$281American Airlines
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
5:00 am - 9:58 am
ORD
-
HRL
4h 58m
1 stop
American Airlines Logo
5:51 am - 12:18 pm
HRL
-
ORD
6h 27m
1 stop
$291American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
4:58 pm - 12:43 am
HRL
-
ORD
7h 45m
1 stop
$305American Airlines
Tue, Oct 27 - Sat, Oct 31
United Airlines Logo
4:57 pm - 9:44 pm
ORD
-
HRL
4h 47m
1 stop
United Airlines Logo
5:16 pm - 12:15 am
HRL
-
ORD
6h 59m
1 stop
$310United Airlines
Tue, Aug 4 - Tue, Aug 11
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
6:43 pm - 12:18 am
HRL
-
ORD
5h 35m
1 stop
$331American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
12:05 pm - 8:12 pm
ORD
-
HRL
8h 07m
1 stop
American Airlines Logo
5:18 pm - 12:50 am
HRL
-
ORD
7h 32m
1 stop
$336American Airlines
Wed, Jul 29 - Wed, Aug 5
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
10:34 am - 3:55 pm
HRL
-
ORD
5h 21m
1 stop
$342American Airlines
Tue, Nov 24 - Wed, Dec 2
American Airlines Logo
8:55 am - 3:31 pm
ORD
-
HRL
6h 36m
1 stop
American Airlines Logo
4:02 pm - 10:19 pm
HRL
-
ORD
6h 17m
1 stop
$359American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Harlingen flights

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Harlingen departing in September.

What is the cheapest Chicago to Harlingen flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Harlingen costs $496 on the route between Chicago O'Hare Intl Airport (ORD) and Harlingen (HRL). It is also the most popular route.

What is the cheapest month to fly from Chicago to Harlingen?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Harlingen, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Harlingen is January, where tickets cost $134 (return) on average. On the other hand, the most expensive months are May and July, where the average cost of round-trip tickets is $296 and $289 respectively.

Good to know

Low seasonNovember
Cheapest flight$165
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Harlingen

When to book flights from Chicago to Harlingen

Are your dates flexible? Find out the best times to travel from Chicago 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 flights from Chicago to Harlingen

  • What is the cheapest flight from Chicago to Harlingen?

    In the last 5 days, the lowest price for a flight from Chicago to Harlingen was $165 for a one-way ticket and $206 for a round-trip.

  • Do I need a passport to fly between Chicago 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 airports will I be using when flying from Chicago to Harlingen?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Harlingen Valley Intl.

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Harlingen flight route.

  • Which airline alliances offer flights from Chicago to Harlingen?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Harlingen, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Harlingen, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Harlingen are Southwest and United Airlines. With an average price for the route of $361 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $358 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago 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 to Harlingen.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Harlingen from Chicago 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago 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 Chicago 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.
7.9
SouthwestOverall score based on 4234 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

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

Information on your arrival and departure airports