CHI - HRL

$135 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 1/15. 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
$251
Overall average: $295
United Airlines
Tue 1/6Tue 1/13
ORD - HRL • 1 stop
Cheapest one-way
$135
Typical prices: $108-$126
American Airlines
Thu 1/15
ORD - HRL • 1 stop
Top airlines
United Airlines
Cheapest • from $251 (round-trip)
Southwest
Best reviews • 7.9 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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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, Jan 6 - Tue, Jan 13
United Airlines Logo
2:12 pm - 8:01 pm
ORD
-
HRL
5h 49m1 stop
United Airlines Logo
5:25 pm - 10:58 pm
HRL
-
ORD
5h 33m1 stop
$251United Airlines
Wed, Jan 21 - Mon, Jan 26
American Airlines Logo
11:56 am - 6:14 pm
ORD
-
HRL
6h 18m1 stop
American Airlines Logo
6:44 pm - 11:44 pm
HRL
-
ORD
5h 00m1 stop
$260American Airlines
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
5:05 am - 10:36 am
ORD
-
HRL
5h 31m1 stop
American Airlines Logo
3:22 pm - 10:09 pm
HRL
-
ORD
6h 47m1 stop
$269American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
5:11 pm - 10:52 pm
ORD
-
HRL
5h 41m1 stop
American Airlines Logo
6:00 am - 10:47 am
HRL
-
ORD
4h 47m1 stop
$280American Airlines
Sat, Mar 14 - Fri, Mar 20
Southwest Logo
2:40 pm - 11:55 pm
ORD
-
HRL
9h 15m2 stops
Southwest Logo
6:50 am - 2:20 pm
HRL
-
ORD
7h 30m1 stop
$324Southwest
Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
8:54 am - 4:06 pm
ORD
-
HRL
7h 12m1 stop
United Airlines Logo
12:10 pm - 7:49 pm
HRL
-
ORD
7h 39m1 stop
$331United Airlines
Wed, Feb 11 - Thu, Feb 19
Southwest Logo
2:15 pm - 9:50 pm
ORD
-
HRL
7h 35m2 stops
Southwest Logo
5:40 am - 1:00 pm
HRL
-
ORD
7h 20m2 stops
$333Southwest
Mon, Dec 22 - Fri, Dec 26
United Airlines Logo
4:00 pm - 9:59 pm
ORD
-
HRL
5h 59m1 stop
United Airlines Logo
5:00 am - 10:08 am
HRL
-
ORD
5h 08m1 stop
$375United Airlines
Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
8:54 am - 4:06 pm
ORD
-
HRL
7h 12m1 stop
United Airlines Logo
5:25 pm - 11:45 am
HRL
-
ORD
18h 20m2 stops
$382United Airlines
Mon, Dec 22 - Fri, Dec 26
United Airlines Logo
4:00 pm - 9:59 pm
ORD
-
HRL
5h 59m1 stop
United Airlines Logo
5:00 am - 10:08 am
HRL
-
ORD
5h 08m1 stop
$383United 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.

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’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 Saturday, 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.

Good to know

Low seasonApril
Cheapest flight$135
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 24% 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 $135 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Harlingen, with Star Alliance 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 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $380 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.
7.9
SouthwestOverall score based on 4252 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025
DCA - DAL
Read more Southwest reviews

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.

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.

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.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

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.

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.

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

Information on your arrival and departure airports