Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Harlingen from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Harlingen departing on 6/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Harlingen

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 10:16 am
ORD
-
HRL
5h 16m
1 stop
American Airlines Logo
4:58 pm - 12:06 am
HRL
-
ORD
7h 08m
1 stop
$261American Airlines
Tue, Sep 15 - Sat, Sep 19
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
American Airlines Logo
5:18 pm - 12:42 am
HRL
-
ORD
7h 24m
1 stop
$293American Airlines
Tue, May 26 - Sat, May 30
United Airlines Logo
6:30 am - 1:30 pm
ORD
-
HRL
7h 00m
1 stop
United Airlines Logo
5:20 pm - 11:15 pm
HRL
-
ORD
5h 55m
1 stop
$298United Airlines
Tue, Jun 2 - Sat, Jun 13
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
American Airlines Logo
4:57 pm - 12:39 am
HRL
-
ORD
7h 42m
1 stop
$303American Airlines
Sat, May 30 - Fri, Jun 12
American Airlines Logo
8:19 am - 4:25 pm
ORD
-
HRL
8h 06m
1 stop
American Airlines Logo
5:18 pm - 12:39 am
HRL
-
ORD
7h 21m
1 stop
$309American Airlines
Tue, Jun 9 - Sat, Jun 20
American Airlines Logo
5:00 am - 10:04 am
ORD
-
HRL
5h 04m
1 stop
American Airlines Logo
3:17 pm - 11:10 pm
HRL
-
ORD
7h 53m
1 stop
$319American Airlines
Sat, Aug 15 - Mon, Aug 31
American Airlines Logo
5:00 am - 10:12 am
ORD
-
HRL
5h 12m
1 stop
American Airlines Logo
4:58 pm - 11:39 pm
HRL
-
ORD
6h 41m
1 stop
$326American Airlines
Fri, Jul 3 - Tue, Jul 7
United Airlines Logo
2:15 pm - 9:54 pm
ORD
-
HRL
7h 39m
1 stop
United Airlines Logo
5:10 am - 10:20 am
HRL
-
ORD
5h 10m
1 stop
$345United Airlines
Thu, Jul 30 - Thu, Aug 6
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
American Airlines Logo
5:22 pm - 12:50 am
HRL
-
ORD
7h 28m
1 stop
$346American Airlines
Wed, Jul 1 - Wed, Jul 15
American Airlines Logo
4:44 pm - 12:14 am
ORD
-
HRL
7h 30m
1 stop
American Airlines Logo
5:18 pm - 11:32 pm
HRL
-
ORD
6h 14m
1 stop
$357American Airlines
Sat, May 30 - Sat, Jun 6

American Airlines flights from Chicago to Harlingen

Our best American Airlines deals on Chicago to Harlingen flight tickets
American Airlines
Sep 15
ORD5:00 amChicago O'Hare Intl
5h 16m
1 stop
HRL10:16 amHarlingen Valley Intl
Sep 19
HRL4:58 pmHarlingen Valley Intl
7h 08m
1 stop
ORD12:06 amChicago O'Hare Intl
$261
American Airlines
May 26
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
HRL10:13 amHarlingen Valley Intl
May 30
HRL5:18 pmHarlingen Valley Intl
7h 24m
1 stop
ORD12:42 amChicago O'Hare Intl
$293
American Airlines
May 30
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
HRL10:13 amHarlingen Valley Intl
Jun 12
HRL4:57 pmHarlingen Valley Intl
7h 42m
1 stop
ORD12:39 amChicago O'Hare Intl
$303

United Airlines flights from Chicago to Harlingen

Our best United Airlines deals on Chicago to Harlingen flight tickets
United Airlines
Jun 2
ORD6:30 amChicago O'Hare Intl
7h 00m
1 stop
HRL1:30 pmHarlingen Valley Intl
Jun 13
HRL5:20 pmHarlingen Valley Intl
5h 55m
1 stop
ORD11:15 pmChicago O'Hare Intl
$298
United Airlines
Jul 30
ORD2:15 pmChicago O'Hare Intl
7h 39m
1 stop
HRL9:54 pmHarlingen Valley Intl
Aug 6
HRL5:10 amHarlingen Valley Intl
5h 10m
1 stop
ORD10:20 amChicago O'Hare Intl
$345
United Airlines
May 27
ORD7:30 amChicago O'Hare Intl
6h 00m
1 stop
HRL1:30 pmHarlingen Valley Intl
May 30
HRL5:20 pmHarlingen Valley Intl
7h 25m
1 stop
ORD12:45 amChicago O'Hare Intl
$366

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Harlingen that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 16, 2026.
Use the filters below to find and compare flights from Chicago to Harlingen that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 9/15

5:00 am-10:16 am

1 stop5h 16m

Harlingen Valley Intl

Sat 9/19

4:58 pm-12:06 am

1 stop7h 08m

$261

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 5/26

5:00 am-10:13 am

1 stop5h 13m

Harlingen Valley Intl

Sat 5/30

5:18 pm-12:42 am

1 stop7h 24m

$293

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 6/2

6:30 am-1:30 pm

1 stop7h 00m

Harlingen Valley Intl

Sat 6/13

5:20 pm-11:15 pm

1 stop5h 55m

$298

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 5/30

5:00 am-10:13 am

1 stop5h 13m

Harlingen Valley Intl

Fri 6/12

4:57 pm-12:39 am

1 stop7h 42m

$303

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 6/9

8:19 am-4:25 pm

1 stop8h 06m

Harlingen Valley Intl

Sat 6/20

5:18 pm-12:39 am

1 stop7h 21m

$309

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 8/15

5:00 am-10:04 am

1 stop5h 04m

Harlingen Valley Intl

Mon 8/31

3:17 pm-11:10 pm

1 stop7h 53m

$319
Quickest round-trip

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 7/3

5:00 am-10:12 am

1 stop5h 12m

Harlingen Valley Intl

Tue 7/7

4:58 pm-11:39 pm

1 stop6h 41m

$326

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Thu 7/30

2:15 pm-9:54 pm

1 stop7h 39m

Harlingen Valley Intl

Thu 8/6

5:10 am-10:20 am

1 stop5h 10m

$345

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 7/1

5:00 am-10:13 am

1 stop5h 13m

Harlingen Valley Intl

Wed 7/15

5:22 pm-12:50 am

1 stop7h 28m

$346

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 5/30

4:44 pm-12:14 am

1 stop7h 30m

Harlingen Valley Intl

Sat 6/6

5:18 pm-11:32 pm

1 stop6h 14m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

See travel insights to Harlingen from

How to get the cheapest flight ticket from Chicago to Harlingen

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Harlingen?

What is the cheapest month to fly to Harlingen?

If you aren’t able to travel during the month of January, then book flights to Harlingen from Chicago during March instead. Flights to Harlingen in March, while not as cheap as those in January, still average around $156.

What is the cheapest Chicago to Harlingen Valley Intl flight route?

Fly from Chicago O'Hare Intl to Harlingen Valley Intl for the best Chicago - Harlingen Valley Intl flight prices

Can stopping save me money on Chicago to Harlingen flights?

You could potentially save up to 8% on your flight if you consider stops on a Chicago to Harlingen flight.

How have Chicago to Harlingen flight prices changed over time?

When to book flights from Chicago to Harlingen

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Harlingen according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Harlingen (CHI to HRL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Harlingen

Fastest flight time

5h 16m

Direct flights

None
The fastest flight from Chicago to Harlingen takes 5h 16m
There are no direct flights from Chicago to Harlingen. There are no popular flight routes from Chicago to Harlingen.
Search flight deals

Frequently asked questions about flying from Chicago to Harlingen

  • How far is Chicago to Harlingen Valley Intl by plane?

    The straight-line distance from Chicago to Harlingen Valley Intl is 1224.6 mi. Typically, this will take 5h 16m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Harlingen Valley Intl Airport?

    Prices for flights from Chicago to Harlingen Valley Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Harlingen Valley Intl Airport?

  • How old do you have to be to fly from Chicago to Harlingen Valley Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Harlingen Valley Intl Airport.

  • What documentation or ID do you need to fly to Harlingen Valley Intl Airport?

    The travel and health documents you'll need for your trip to Harlingen Valley Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Harlingen Valley Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Harlingen?

  • What is the most popular airline from Chicago to Harlingen?

Best airlines flying from Chicago to Harlingen

Compare and see reviews for airlines that fly from Chicago to Harlingen with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $216Free CancellationRating
8.0
4,295 reviews
Search Southwest flights
American AirlinesPriceFrom $233Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights
United AirlinesPriceFrom $251Free CancellationRating
7.4
9,726 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Harlingen?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Harlingen. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Harlingen with flexible booking policies on momondo?

Yes. All flights to Harlingen from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Harlingen?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Harlingen from Chicago.

I’m not ready to book a flight from Chicago to Harlingen right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Harlingen flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Harlingen trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 6/15
Mon 6/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States