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HRL - CHI

Find cheap flights from Harlingen to Chicago from $229

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 6/10. 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
0 bags
Fri 6/7
Fri 6/14

Search 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
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:05 am - 10:08 amHRL-ORD
5h 03m1 stop
6:00 am - 10:55 amORD-HRL
4h 55m1 stop
$363United Airlines
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Thu, May 23 - Mon, May 27
4:25 pm - 9:25 pmHRL-ORD
5h 00m1 stop
6:00 am - 11:36 amORD-HRL
5h 36m1 stop
$368American Airlines
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Tue, Jun 25 - Sun, Aug 11
9:48 am - 12:12 amHRL-ORD
14h 24m1 stop
6:00 am - 10:55 amORD-HRL
4h 55m1 stop
$396United Airlines
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Wed, May 22 - Sun, May 26
12:06 pm - 6:22 pmHRL-ORD
6h 16m1 stop
5:00 am - 9:33 amORD-HRL
4h 33m1 stop
$458American Airlines
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Fri, Aug 9 - Mon, Aug 12
12:10 pm - 12:12 amHRL-ORD
12h 02m1 stop
10:40 am - 10:51 pmORD-HRL
12h 11m2 stops
$459United Airlines
Find Deal
Wed, May 22 - Sun, May 26
5:54 am - 11:10 amHRL-ORD
5h 16m1 stop
5:00 am - 11:50 amORD-HRL
6h 50m1 stop
$462American Airlines
Find Deal
Thu, May 30 - Tue, Jun 4
5:15 pm - 7:48 amHRL-ORD
14h 33m1 stop
9:31 pm - 3:57 pmORD-HRL
18h 26m1 stop
$519United Airlines
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Mon, Jun 3 - Mon, Jun 10
7:25 am - 7:48 amHRL-ORD
24h 23m1 stop
9:17 pm - 10:49 amORD-HRL
13h 32m2 stops
$523United Airlines
Find Deal
Fri, Aug 9 - Mon, Aug 12
5:05 am - 10:08 amHRL-ORD
5h 03m1 stop
10:45 am - 9:06 pmORD-HRL
10h 21m2 stops
$534United Airlines
Find Deal
Thu, May 23 - Mon, May 27
7:25 am - 7:46 amHRL-ORD
24h 21m1 stop
9:17 pm - 3:55 pmORD-HRL
18h 38m2 stops
$562United Airlines
Find Deal
Tue, Jun 25 - Sun, Aug 11

Flights from Harlingen to Chicago - Travel Insights & Trends

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, Texas to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Harlingen, Texas to Chicago.
Our data shows that the cheapest route for a one-way flight from Harlingen, Texas to Chicago cost $170 and was between Harlingen, Texas and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $345.

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

The average price of all flights from Harlingen, Texas to Chicago clicked on KAYAK for each day over the last 12 months.
For Harlingen to Chicago, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Harlingen, the best deals are generally found on Friday, with Saturday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Harlingen, Texas 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, Texas to Chicago is May, where tickets cost $233 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $623 and $547 respectively.

Which airlines provide the cheapest flights from Harlingen to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Harlingen to Chicago found by KAYAK users in the last 72 hours was for $363 on United Airlines, followed by American Airlines ($368). One-way flight deals have also been found from as low as $229 on American Airlines and from $377 on United Airlines.

Which cabin class options are there for flights between Harlingen, Texas and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Good to know

Low season

February

High season

June

Cheapest flight

$229
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 34% 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, Texas to Chicago?

    In the last 3 days, the lowest price for a flight from Harlingen, Texas to Chicago was $229 for a one-way ticket and $363 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Harlingen to Chicago are United Airlines and American Airlines. With an average price for the route of $447 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $498 and an overall rating of 7.3.

  • 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.

See more FAQs

Top tips for finding a cheap flight from Harlingen to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way.

Top airlines flying 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.
7.4
United AirlinesOverall score based on 11043 reviews
7.7Boarding
7.2Comfort
6.7Food
8.1Crew
7.1Entertainment
Airline reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

8.0 ExcellentMichelle, Apr 2024MBS - ORD
Read more about United Airlines reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Harlingen to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Harlingen to Chicago found on KAYAK in the last 72 hours.
6/10Mon
1 stopAmerican Airlines
7h 16mHRL-ORD
$229
6/10Mon
2 stopsUnited Airlines
14h 50mHRL-ORD
$377

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Last minute flights from Harlingen to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Harlingen to Chicago that are departing in the next 10 days.
5/11Sat
multi-stopUnited Airlines
5h 43mHRL-ORD
5/14Tue
multi-stopUnited Airlines
7h 15mORD-HRL
$324
5/13Mon
multi-stopUnited Airlines
6h 52mHRL-ORD
5/16Thu
multi-stopUnited Airlines
5h 15mORD-HRL
$501
5/10Fri
multi-stopUnited Airlines
5h 48mHRL-ORD
5/14Tue
multi-stopUnited Airlines
10h 29mORD-HRL
$514
5/13Mon
multi-stopUnited Airlines
6h 52mHRL-ORD
5/16Thu
multi-stopUnited Airlines
5h 06mORD-HRL
$530
5/13Mon
multi-stopUnited Airlines
11h 24mHRL-ORD
5/16Thu
multi-stopUnited Airlines
5h 15mORD-HRL
$709
5/11Sat
multi-stopAmerican Airlines
10h 11mHRL-ORD
5/14Tue
multi-stopAmerican Airlines
6h 24mORD-HRL
$983
5/11Sat
multi-stopAmerican Airlines
11h 50mHRL-ORD
5/14Tue
multi-stopAmerican Airlines
5h 19mORD-HRL
$989
5/10Fri
multi-stopUnited Airlines
11h 31mHRL-ORD
5/14Tue
multi-stopUnited Airlines
10h 29mORD-HRL
$1,197

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Harlingen - Chicago Flights

Departure:

Harlingen (undefined)United States

Return flight deals:

Chicago - Harlingen

Cabin classes:

$345