HRL - CHI

$131 Find Cheap Flights from Harlingen to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Harlingen to Chicago departing on 7/1. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Harlingen to Chicago, 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 Harlingen to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$261
Typical prices: $338-$268
American Airlines
Tue 8/11Wed 8/19
HRL - ORD • 1 stop
Cheapest one-way
$131
Typical prices: $118-$183
United Airlines
Wed 7/1
HRL - ORD • 1 stop
Top airlines
Cheapest • from $261 (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 Harlingen and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $314 (round-trip)
Shortest trip • 5h 04m (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 Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Harlingen to Chicago (HRL-CHI)

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

Tue, Aug 11 - Wed, Aug 19
American Airlines Logo
3:17 pm - 11:10 pm
HRL
-
ORD
7h 53m
1 stop
American Airlines Logo
5:00 am - 10:04 am
ORD
-
HRL
5h 04m
1 stop
$261American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
6:45 pm - 11:48 pm
HRL
-
ORD
5h 03m
1 stop
American Airlines Logo
11:43 am - 7:33 pm
ORD
-
HRL
7h 50m
1 stop
$277American Airlines
Thu, Sep 24 - Tue, Sep 29
United Airlines Logo
5:05 am - 11:27 am
HRL
-
ORD
6h 22m
1 stop
United Airlines Logo
4:57 pm - 9:52 pm
ORD
-
HRL
4h 55m
1 stop
$288United Airlines
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
3:45 pm - 8:55 pm
ORD
-
HRL
5h 10m
1 stop
$290Southwest
Tue, May 19 - Sat, May 23
American Airlines Logo
6:45 pm - 11:48 pm
HRL
-
ORD
5h 03m
1 stop
American Airlines Logo
4:44 pm - 12:14 am
ORD
-
HRL
7h 30m
1 stop
$293American Airlines
Fri, Jun 5 - Fri, Jun 12
American Airlines Logo
4:57 pm - 12:39 am
HRL
-
ORD
7h 42m
1 stop
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
$308American Airlines
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
11:55 am - 10:00 pm
ORD
-
HRL
10h 05m
2 stops
$324Southwest
Tue, May 12 - Sat, May 16
Southwest Logo
7:10 am - 1:15 pm
HRL
-
ORD
6h 05m
1 stop
Southwest Logo
2:05 pm - 9:35 pm
ORD
-
HRL
7h 30m
2 stops
$337Southwest
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
5:00 pm - 11:39 pm
HRL
-
ORD
6h 39m
1 stop
American Airlines Logo
12:05 pm - 8:12 pm
ORD
-
HRL
8h 07m
1 stop
$339American Airlines
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
2:40 pm - 10:00 pm
ORD
-
HRL
7h 20m
2 stops
$342Southwest
Booking Insights

KAYAK's insights & trends for Harlingen to Chicago flights

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

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

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

What is the cheapest Harlingen to Chicago flight route?

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

The cheapest return flight from Harlingen to Chicago costs $676 on the route between Harlingen (HRL) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Harlingen to Chicago, 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 Harlingen to Chicago is October, where tickets cost $130 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $377 and $329 respectively.

Good to know

Low seasonJanuary
Cheapest flight$131
Best time to beat the crowds but there is an average 47% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Harlingen to Chicago O'Hare Airport

When to book flights from Harlingen to Chicago

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

  • What is the cheapest flight from Harlingen to Chicago?

    In the last 3 days, the lowest price for a flight from Harlingen to Chicago was $131 for a one-way ticket and $261 for a round-trip.

  • Do I need a passport to fly between Harlingen and Chicago?

    No

  • Which airports will I be using when flying from Harlingen to Chicago?

    On your way to Chicago, you’ll fly out from Harlingen Valley Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Harlingen to Chicago?

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

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

    The two airlines most popular with KAYAK users for flights from Harlingen to Chicago are Southwest and United Airlines. With an average price for the route of $333 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 $358 and an overall rating of 7.4.

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

    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 Harlingen to Chicago.

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

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

    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 Chicago with an airline and back to Harlingen with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Harlingen to Chicago?

    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 Chicago from Harlingen 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 Harlingen to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Harlingen to Chicago. 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 Harlingen to Chicago? 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 4314 reviews
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports