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Cheap flights from Chicago to Harlingen from $150

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 10/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

American Airlines Logo
11:46 am - 6:10 pmORD-HRL
6h 24m1 stop
American Airlines Logo
6:40 pm - 11:37 pmHRL-ORD
4h 57m1 stop
$251American Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
American Airlines Logo
6:48 pm - 12:01 amORD-HRL
5h 13m1 stop
American Airlines Logo
5:50 am - 11:03 amHRL-ORD
5h 13m1 stop
$293American Airlines
Find Deal
Thu, Feb 19 - Wed, Feb 25
Sun Country Air Logo
2:00 pm - 10:48 amORD-HRL
20h 48m1 stop
Sun Country Air Logo
11:47 am - 10:39 amHRL-ORD
22h 52m1 stop
$295Sun Country Air
Find Deal
Wed, Oct 1 - Sun, Oct 5
United Airlines Logo
2:15 pm - 9:44 pmORD-HRL
7h 29m1 stop
United Airlines Logo
5:16 pm - 10:36 pmHRL-ORD
5h 20m1 stop
$317United Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
Southwest Logo
4:20 pm - 9:25 pmORD-HRL
5h 05m1 stop
Southwest Logo
7:00 am - 1:05 pmHRL-ORD
6h 05m1 stop
$319Southwest
Find Deal
Wed, Oct 1 - Mon, Oct 6
Southwest Logo
7:30 am - 2:55 pmORD-HRL
7h 25m2 stops
Southwest Logo
7:00 am - 1:05 pmHRL-ORD
6h 05m1 stop
$324Southwest
Find Deal
Wed, Oct 1 - Mon, Oct 6
American Airlines Logo
11:46 am - 6:10 pmORD-HRL
6h 24m1 stop
American Airlines Logo
6:40 pm - 11:37 pmHRL-ORD
4h 57m1 stop
$334American Airlines
Find Deal
Fri, Nov 7 - Tue, Nov 11
United Airlines Logo
2:21 pm - 7:39 pmORD-HRL
5h 18m1 stop
United Airlines Logo
7:00 am - 12:15 amHRL-ORD
17h 15m1 stop
$366United Airlines
Find Deal
Sat, Nov 1 - Sun, Nov 9
Sun Country Air Logo
11:45 am - 10:53 amORD-HRL
23h 08m1 stop
Sun Country Air Logo
11:49 am - 6:50 pmHRL-ORD
7h 01m1 stop
$372Sun Country Air
Find Deal
Wed, Dec 31 - Sun, Jan 4
United Airlines Logo
9:00 am - 4:13 pmORD-HRL
7h 13m1 stop
United Airlines Logo
5:00 am - 11:05 amHRL-ORD
6h 05m1 stop
$379United Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3

United Airlines flights from Chicago to Harlingen, Texas

Our best United Airlines deals on Chicago to Harlingen, Texas flight tickets
United Airlines
Mar 10
ORD2:15 pmChicago O'Hare Intl
7h 29m
1 stop
HRL9:44 pmHarlingen Valley Intl
Mar 11
HRL5:16 pmHarlingen Valley Intl
5h 20m
1 stop
ORD10:36 pmChicago O'Hare Intl
$317
Find similar
United Airlines
Nov 1
ORD2:21 pmChicago O'Hare Intl
5h 18m
1 stop
HRL7:39 pmHarlingen Valley Intl
Nov 9
HRL7:00 amHarlingen Valley Intl
17h 15m
1 stop
ORD12:15 amChicago O'Hare Intl
$366
Find similar
United Airlines
Sep 29
ORD9:00 amChicago O'Hare Intl
7h 13m
1 stop
HRL4:13 pmHarlingen Valley Intl
Oct 3
HRL5:00 amHarlingen Valley Intl
6h 05m
1 stop
ORD11:05 amChicago O'Hare Intl
$379
Find similar

Sun Country Air flights from Chicago to Harlingen, Texas

Our best Sun Country Air deals on Chicago to Harlingen, Texas flight tickets
Sun Country Air
Oct 1
ORD2:00 pmChicago O'Hare Intl
20h 48m
1 stop
HRL10:48 amHarlingen Valley Intl
Oct 5
HRL11:47 amHarlingen Valley Intl
22h 52m
1 stop
ORD10:39 amChicago O'Hare Intl
$295
Find similar
Sun Country Air
Dec 31
ORD11:45 amChicago O'Hare Intl
23h 08m
1 stop
HRL10:53 amHarlingen Valley Intl
Jan 4
HRL11:49 amHarlingen Valley Intl
7h 01m
1 stop
ORD6:50 pmChicago O'Hare Intl
$372
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Harlingen, Texas 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Harlingen, Texas that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 11/8

11:46 am-6:10 pm

1 stop6h 24m

Harlingen Valley Intl

Tue 11/11

6:40 pm-11:37 pm

1 stop4h 57m

$251

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Thu 2/19

6:48 pm-12:01 am

1 stop5h 13m

Harlingen Valley Intl

Wed 2/25

5:50 am-11:03 am

1 stop5h 13m

$293

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 10/1

2:00 pm-10:48 am

1 stop20h 48m

Harlingen Valley Intl

Sun 10/5

11:47 am-10:39 am

1 stop22h 52m

$295

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 3/10

2:15 pm-9:44 pm

1 stop7h 29m

Harlingen Valley Intl

Wed 3/11

5:16 pm-10:36 pm

1 stop5h 20m

$317

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 10/1

4:20 pm-9:25 pm

1 stop5h 05m

Harlingen Valley Intl

Mon 10/6

7:00 am-1:05 pm

1 stop6h 05m

$319

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 10/1

7:30 am-2:55 pm

2 stops7h 25m

Harlingen Valley Intl

Mon 10/6

7:00 am-1:05 pm

1 stop6h 05m

$324

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 11/7

11:46 am-6:10 pm

1 stop6h 24m

Harlingen Valley Intl

Tue 11/11

6:40 pm-11:37 pm

1 stop4h 57m

$334

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 11/1

2:21 pm-7:39 pm

1 stop5h 18m

Harlingen Valley Intl

Sun 11/9

7:00 am-12:15 am

1 stop17h 15m

$366

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 12/31

11:45 am-10:53 am

1 stop23h 08m

Harlingen Valley Intl

Sun 1/4

11:49 am-6:50 pm

1 stop7h 01m

$372

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 9/29

9:00 am-4:13 pm

1 stop7h 13m

Harlingen Valley Intl

Fri 10/3

5:00 am-11:05 am

1 stop6h 05m

$379

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Harlingen from

How to get the cheapest flight ticket from Chicago to Harlingen, Texas

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 cheapest month to fly to Harlingen, Texas?

The month of April is, on average, the cheapest month to fly to Harlingen, Texas from Chicago, with most prices found around $273. If you are unable to visit Harlingen, Texas during the month of April, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $316.

What is the cheapest day to depart on your flight to Harlingen, Texas?

The cheapest day to depart on your flight to Harlingen, Texas is on a Wednesday when prices can be found for as low as $295. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Harlingen, Texas for around $482.

What is the cheapest time of day to depart on your flight to Harlingen, Texas?

Our most recent data shows that the best time of day to fly to Harlingen, Texas is in the evening. Flights from Chicago to Harlingen, Texas during this time can be as low as $347. Flights in the morning are often more expensive with an average ticket price of $433.

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

What cabin class options are available on Chicago to Harlingen Valley Intl flights?

There is only 1 cabin class available to choose from on Chicago to Harlingen Valley Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago to Harlingen, Texas

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

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

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

Direct flights

None
There are no direct flights from Chicago to Harlingen, Texas. There are no popular flight routes from Chicago to Harlingen, Texas.
Search flight deals

  • 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 05m 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, Texas?

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

Best airlines flying from Chicago to Harlingen, Texas

Compare and see reviews for airlines that fly from Chicago to Harlingen, Texas with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $208Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $267Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to Harlingen, Texas

    Southwest flight deals from Chicago to Harlingen, Texas start from $208 round-trip. Over the 3 Southwest flights for this route in a normal week, average airfare is usually $382 round-trip - but some users have found much cheaper deals with momondo.

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.

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