HRL - CHI

$126 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 5/21. 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.
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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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Harlingen to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Harlingen to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
8:10 pm - 12:59 amHRL-ORD
4h 49m1 stop
American Airlines Logo
1:28 pm - 7:40 pmORD-HRL
6h 12m1 stop
$251American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
5:20 pm - 11:12 pmHRL-ORD
5h 52m1 stop
United Airlines Logo
6:00 am - 1:25 pmORD-HRL
7h 25m1 stop
$260United Airlines
Find Deal
Wed, Jun 4 - Sun, Jun 8
American Airlines Logo
7:59 pm - 12:59 amHRL-ORD
5h 00m1 stop
American Airlines Logo
4:56 pm - 12:04 amORD-HRL
7h 08m1 stop
$269American Airlines
Find Deal
Mon, Jun 16 - Fri, Jun 20
United Airlines Logo
5:20 pm - 12:13 amHRL-ORD
6h 53m1 stop
United Airlines Logo
7:10 am - 1:25 pmORD-HRL
6h 15m1 stop
$285United Airlines
Find Deal
Mon, Jun 9 - Fri, Jun 13
United Airlines Logo
5:20 pm - 12:13 amHRL-ORD
6h 53m1 stop
United Airlines Logo
9:21 am - 4:00 pmORD-HRL
6h 39m1 stop
$304United Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
United Airlines Logo
5:10 am - 10:21 amHRL-ORD
5h 11m1 stop
United Airlines Logo
2:26 pm - 7:35 pmORD-HRL
5h 09m1 stop
$305United Airlines
Find Deal
Wed, Jul 9 - Fri, Jul 18
American Airlines Logo
7:59 pm - 12:59 amHRL-ORD
5h 00m1 stop
American Airlines Logo
5:00 am - 9:35 amORD-HRL
4h 35m1 stop
$309American Airlines
Find Deal
Thu, Jun 19 - Sun, Jun 22
Southwest Logo
6:00 am - 3:00 pmHRL-ORD
9h 00m2 stops
Southwest Logo
4:20 pm - 9:45 pmORD-HRL
5h 25m1 stop
$319Southwest
Find Deal
Wed, Jul 9 - Fri, Jul 18
Southwest Logo
7:00 am - 3:00 pmHRL-ORD
8h 00m2 stops
Southwest Logo
7:30 am - 4:40 pmORD-HRL
9h 10m1 stop
$365Southwest
Find Deal
Thu, May 29 - Tue, Jun 3
Southwest Logo
2:15 pm - 9:30 pmHRL-ORD
7h 15m2 stops
Southwest Logo
4:20 pm - 9:45 pmORD-HRL
5h 25m1 stop
$374Southwest
Find Deal
Mon, Jun 16 - Fri, Jun 20
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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.

What is the cheapest Harlingen to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Harlingen to Chicago.

Our data shows that the cheapest route for a return flight from Harlingen to Chicago cost $717 and was between Harlingen (HRL) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $717.

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

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

If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Harlingen to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

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 May, where tickets cost $233 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $458 and $407 respectively.

Can I save money by flying with a layover from Harlingen to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $253, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$126
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 10% increase in price.
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 $126 for a one-way ticket and $251 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?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Harlingen to Chicago flight 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 $332 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 $362 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.

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 4293 reviews
8.2Boarding
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The last 30 min or so, they put the heat on full. We thought we were being basted.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

The plane wasn’t full, so we got the best seats

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

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