CHI - HRL

$150 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 10/12. 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

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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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

Sat, Oct 25 - Tue, Oct 28
American Airlines Logo
5:17 pm - 11:04 pmORD-HRL
5h 47m1 stop
American Airlines Logo
6:37 pm - 11:42 pmHRL-ORD
5h 05m1 stop
$251American Airlines
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Fri, Nov 7 - Tue, Nov 11
American Airlines Logo
11:46 am - 6:10 pmORD-HRL
6h 24m1 stop
American Airlines Logo
6:40 pm - 11:37 pmHRL-ORD
4h 57m1 stop
$334American Airlines
Find Deal
Wed, Dec 31 - Sun, Jan 4
Sun Country Air Logo
11:45 am - 10:53 amORD-HRL
23h 08m1 stop
Sun Country Air Logo
11:49 am - 6:50 pmHRL-ORD
7h 01m1 stop
$372Sun Country Air
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Mon, Sep 29 - Fri, Oct 3
United Airlines Logo
9:00 am - 4:13 pmORD-HRL
7h 13m1 stop
United Airlines Logo
5:00 am - 11:05 amHRL-ORD
6h 05m1 stop
$379United Airlines
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Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
6:00 am - 11:35 amORD-HRL
5h 35m1 stop
American Airlines Logo
5:50 am - 10:58 amHRL-ORD
5h 08m1 stop
$384American Airlines
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Sat, Oct 25 - Tue, Oct 28
United Airlines Logo
7:40 pm - 10:59 amORD-HRL
15h 19m2 stops
United Airlines Logo
5:00 pm - 12:15 amHRL-ORD
7h 15m1 stop
$385United Airlines
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Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
7:10 am - 7:39 pmORD-HRL
12h 29m2 stops
United Airlines Logo
5:00 pm - 12:15 amHRL-ORD
7h 15m1 stop
$403United Airlines
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Fri, Nov 21 - Fri, Nov 28
Southwest Logo
2:15 pm - 11:35 pmORD-HRL
9h 20m2 stops
Southwest Logo
5:45 am - 12:15 pmHRL-ORD
6h 30m2 stops
$429Southwest
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Thu, Oct 9 - Sun, Oct 12
United Airlines Logo
9:00 am - 7:41 pmORD-HRL
10h 41m1 stop
United Airlines Logo
5:17 pm - 12:14 amHRL-ORD
6h 57m1 stop
$437United Airlines
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Sun, Oct 12 - Sun, Oct 19
Southwest Logo
3:10 pm - 11:05 pmORD-HRL
7h 55m1 stop
Southwest Logo
6:50 am - 3:20 pmHRL-ORD
8h 30m2 stops
$524Southwest
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $251 (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
When to travel
April
Cheapest • 29% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$251
Overall average: $420
American Airlines
Sat 10/25Tue 10/28
ORD - HRL • 1 stop
Cheapest one-way
$150
Typical prices: $274-289
Delta
Sun 10/12
ORD - HRL • 1 stop
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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!
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 $518 on the route between Chicago O'Hare Intl Airport (ORD) and Harlingen (HRL). It is also the most popular route.

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

The average price of all round-trip flights from Chicago to Harlingen clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Harlingen, look for departures on Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Harlingen, Tuesday is the cheapest day to fly and Saturday is the most expensive.

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 April, where tickets cost $273 (return) on average. On the other hand, the most expensive months are November and September, where the average cost of round-trip tickets is $473 and $471 respectively.

Good to know

Low seasonSeptember
Cheapest flight$150
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 15% 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 $150 for a one-way ticket and $251 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Harlingen, with SkyTeam 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 $389 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 $388 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 4242 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

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