HRL - CHI

$129 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 4/13. 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
$237
American Airlines
Tue 4/21Sat 4/25
HRL - ORD • 1 stop
Cheapest one-way
$129
Typical prices: $139-$181
Southwest
Mon 4/13
HRL - ORD • 1 stop
Top airlines
Cheapest • from $237 (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 $282 (round-trip)
Shortest trip • 4h 58m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
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

Tue, Apr 21 - Sat, Apr 25
American Airlines Logo
6:45 pm - 11:48 pm
HRL
-
ORD
5h 03m
1 stop
American Airlines Logo
5:00 am - 10:17 am
ORD
-
HRL
5h 17m
1 stop
$237American Airlines
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
7:10 am - 1:15 pm
HRL
-
ORD
6h 05m
1 stop
Southwest Logo
4:15 pm - 11:00 pm
ORD
-
HRL
6h 45m
2 stops
$242Southwest
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
6:20 am - 6:25 pm
HRL
-
ORD
12h 05m
2 stops
Southwest Logo
2:05 pm - 9:35 pm
ORD
-
HRL
7h 30m
2 stops
$253Southwest
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
11:55 am - 5:20 pm
ORD
-
HRL
5h 25m
1 stop
$257Southwest
Sun, May 17 - Wed, May 20
Southwest Logo
7:00 am - 1:15 pm
HRL
-
ORD
6h 15m
1 stop
Southwest Logo
2:40 pm - 10:00 pm
ORD
-
HRL
7h 20m
2 stops
$262Southwest
Wed, Apr 15 - Mon, Apr 20
American Airlines Logo
2:47 pm - 10:45 pm
HRL
-
ORD
7h 58m
1 stop
American Airlines Logo
5:00 am - 10:17 am
ORD
-
HRL
5h 17m
1 stop
$274American Airlines
Thu, Apr 23 - Tue, Apr 28
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
$282Southwest
Sun, Apr 19 - Sun, Apr 26
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
$296United Airlines
Sat, Apr 25 - Wed, Apr 29
Southwest Logo
6:05 am - 9:55 pm
HRL
-
ORD
15h 50m
2 stops
Southwest Logo
11:55 am - 10:00 pm
ORD
-
HRL
10h 05m
2 stops
$300Southwest
Sun, Apr 19 - Sun, Apr 26
Southwest Logo
6:00 am - 3:30 pm
HRL
-
ORD
9h 30m
2 stops
Southwest Logo
3:45 pm - 11:00 pm
ORD
-
HRL
7h 15m
1 stop
$308Southwest
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.

Good to know

Low seasonMay
Cheapest flight$129
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 3% 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 $129 for a one-way ticket and $237 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.

  • 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 airline 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.
8.0
SouthwestOverall score based on 4317 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

I elected to pay for the upgrades and found very little difference

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

I elected to pay for the upgrades and found very little difference

WiFi was not working and didn’t have a beverage service

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

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.

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

Information on your arrival and departure airports