CHI - HRL

$129 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 4/9. 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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$257
Overall average: $400
United Airlines
ven 4/17lun 4/20
ORD - HRL • 1 stop
Cheapest one-way
$129
Typical prices: $143-$194
American Airlines
gio 4/9
ORD - HRL • 1 stop
Top airlines
Cheapest • from $257 (round-trip)
Best reviews • 8.0 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 04m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Start a new search
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

ven, apr 17 - lun, apr 20
United Airlines Logo
5:48 am - 11:23 am
ORD
-
HRL
5h 35m
1 stop
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
$257United Airlines
gio, apr 23 - lun, apr 27
Southwest Logo
2:40 pm - 11:00 pm
ORD
-
HRL
8h 20m
2 stops
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
$262Southwest
gio, apr 23 - lun, apr 27
United Airlines Logo
2:05 pm - 7:40 pm
ORD
-
HRL
5h 35m
1 stop
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
$281United Airlines
dom, apr 26 - ven, mag 8
United Airlines Logo
5:48 am - 11:23 am
ORD
-
HRL
5h 35m
1 stop
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
$284United Airlines
ven, apr 3 - dom, apr 12
Southwest Logo
2:40 pm - 12:05 am
ORD
-
HRL
9h 25m
2 stops
Southwest Logo
7:00 am - 1:15 pm
HRL
-
ORD
6h 15m
1 stop
$292Southwest
gio, apr 2 - mer, apr 8
American Airlines Logo
11:45 am - 7:36 pm
ORD
-
HRL
7h 51m
1 stop
American Airlines Logo
2:47 pm - 10:45 pm
HRL
-
ORD
7h 58m
1 stop
$297American Airlines
lun, apr 27 - ven, mag 8
Southwest Logo
4:15 pm - 11:00 pm
ORD
-
HRL
6h 45m
2 stops
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
$302Southwest
ven, apr 3 - dom, apr 12
Southwest Logo
3:50 pm - 10:10 pm
ORD
-
HRL
6h 20m
1 stop
Southwest Logo
7:00 am - 1:15 pm
HRL
-
ORD
6h 15m
1 stop
$317Southwest
dom, mag 3 - mar, mag 5
Southwest Logo
3:45 pm - 11:50 pm
ORD
-
HRL
8h 05m
2 stops
Southwest Logo
7:10 am - 1:15 pm
HRL
-
ORD
6h 05m
1 stop
$318Southwest
sab, apr 11 - dom, apr 19
Southwest Logo
2:05 pm - 9:35 pm
ORD
-
HRL
7h 30m
2 stops
Southwest Logo
7:00 am - 1:15 pm
HRL
-
ORD
6h 15m
1 stop
$322Southwest
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$129
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 27% 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 $129 for a one-way ticket and $257 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 $393 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 $348 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 4320 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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 ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

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.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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

Information on your arrival and departure airports