CHI - HRL

$155 Find Cheap Flights from Chicago to Harlingen

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 2/15. 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
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Everything you should know

Cheapest round-trip
$211
Typical prices: $394-$542
United Airlines
Tue 3/10Thu 3/19
ORD - HRL • 1 stop
Cheapest one-way
$155
Typical prices: $128-$224
American Airlines
Sun 2/15
ORD - HRL • 1 stop
Top airlines
United Airlines
Cheapest • from $211 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
HRL
Cheapest
ORD
-
HRL
Most popular
Insights
Insights
Insights
Insights
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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, Mar 10 - Thu, Mar 19
United Airlines Logo
2:10 pm - 9:56 pm
ORD
-
HRL
7h 46m
1 stop
United Airlines Logo
5:25 pm - 12:26 am
HRL
-
ORD
7h 01m
1 stop
$211United Airlines
Wed, Feb 25 - Sat, Feb 28
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
6:46 pm - 11:36 pm
HRL
-
ORD
4h 50m
1 stop
$251American Airlines
Wed, Feb 25 - Thu, Mar 5
United Airlines Logo
2:00 pm - 9:59 pm
ORD
-
HRL
7h 59m
1 stop
United Airlines Logo
5:25 pm - 12:26 am
HRL
-
ORD
7h 01m
1 stop
$260United Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
8:06 pm - 12:55 am
HRL
-
ORD
4h 49m
1 stop
$269American Airlines
Sat, Feb 14 - Tue, Feb 24
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
6:46 pm - 11:36 pm
HRL
-
ORD
4h 50m
1 stop
$280American Airlines
Fri, Feb 20 - Fri, Feb 27
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
8:06 pm - 12:55 am
HRL
-
ORD
4h 49m
1 stop
$289American Airlines
Wed, Feb 11 - Tue, Feb 24
United Airlines Logo
7:35 am - 4:06 pm
ORD
-
HRL
8h 31m
1 stop
United Airlines Logo
12:10 pm - 7:53 pm
HRL
-
ORD
7h 43m
1 stop
$305United Airlines
Tue, Feb 10 - Sat, Feb 14
United Airlines Logo
7:35 am - 4:06 pm
ORD
-
HRL
8h 31m
1 stop
United Airlines Logo
5:22 pm - 12:26 am
HRL
-
ORD
7h 04m
1 stop
$309United Airlines
Fri, Feb 27 - Tue, Mar 3
United Airlines Logo
5:45 am - 11:24 am
ORD
-
HRL
5h 39m
1 stop
United Airlines Logo
5:22 pm - 11:04 pm
HRL
-
ORD
5h 42m
1 stop
$313United Airlines
Wed, Feb 25 - Thu, Mar 5
Southwest Logo
1:45 pm - 9:50 pm
ORD
-
HRL
8h 05m
2 stops
Southwest Logo
6:50 am - 2:20 pm
HRL
-
ORD
7h 30m
1 stop
$314Southwest
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.

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.

Good to know

Low seasonApril
Cheapest flight$155
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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 3 days, the lowest price for a flight from Chicago to Harlingen was $155 for a one-way ticket and $211 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 $343 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $398 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 3 airlines serving 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.
8.0
SouthwestOverall score based on 4267 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
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.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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

Information on your arrival and departure airports