HRL - CHI

$106 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 3/11. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$211
Overall average: $466
United Airlines
Thu 4/23Mon 4/27
HRL - ORD • 1 stop
Cheapest one-way
$106
Typical prices: $219-$314
Southwest
Wed 3/11
HRL - ORD • 1 stop
Top airlines
United Airlines
Cheapest • from $211 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
HRL
-
ORD
Cheapest
HRL
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 22% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Thu, Apr 23 - Mon, Apr 27
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
United Airlines Logo
5:48 am - 11:23 am
ORD
-
HRL
5h 35m
1 stop
$211United Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
8:06 pm - 12:55 am
HRL
-
ORD
4h 49m
1 stop
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
$269American Airlines
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
2:40 pm - 11:00 pm
ORD
-
HRL
8h 20m
2 stops
$280Southwest
Wed, Feb 11 - Sun, Feb 15
American Airlines Logo
6:44 pm - 11:44 pm
HRL
-
ORD
5h 00m
1 stop
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
$309American Airlines
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
6:00 am - 3:30 pm
HRL
-
ORD
9h 30m
2 stops
Southwest Logo
2:40 pm - 11:00 pm
ORD
-
HRL
8h 20m
2 stops
$349Southwest
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
12:10 pm - 7:53 pm
HRL
-
ORD
7h 43m
1 stop
United Airlines Logo
9:05 am - 9:59 pm
ORD
-
HRL
12h 54m
2 stops
$394United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
12:10 pm - 7:53 pm
HRL
-
ORD
7h 43m
1 stop
United Airlines Logo
2:00 pm - 7:58 pm
ORD
-
HRL
5h 58m
1 stop
$411United Airlines
Sat, May 23 - Mon, May 25
American Airlines Logo
4:56 pm - 12:26 am
HRL
-
ORD
7h 30m
1 stop
American Airlines Logo
5:00 am - 10:15 am
ORD
-
HRL
5h 15m
1 stop
$437American Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
12:10 pm - 7:53 pm
HRL
-
ORD
7h 43m
1 stop
United Airlines Logo
7:40 pm - 11:24 am
ORD
-
HRL
15h 44m
2 stops
$444United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
12:10 pm - 9:30 am
HRL
-
ORD
21h 20m
2 stops
United Airlines Logo
9:05 am - 9:59 pm
ORD
-
HRL
12h 54m
2 stops
$472United Airlines
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.

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 May, where tickets cost $257 (return) on average. On the other hand, the most expensive months are January and June, where the average cost of round-trip tickets is $514 and $442 respectively.

Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds but there is an average 56% increase in price.
Most popular time to fly with an average 1% 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 $106 for a one-way ticket and $211 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Harlingen and Chicago, with Star Alliance 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 4267 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great vacation. Can't wait till next year for another one.

The seats were comfortable, and the boarding process was pretty smooth.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Information on your arrival and departure airports