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Cheap flights from Chicago to Harlingen from $131

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 8/25. 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

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Find the cheapest flights from Chicago to Harlingen

Cheap round-trip flights

American Airlines Logo
6:00 am - 2:19 pmORD-HRL
8h 19m1 stop
American Airlines Logo
6:35 pm - 11:59 pmHRL-ORD
5h 24m1 stop
$247American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
6:00 am - 2:19 pmORD-HRL
8h 19m1 stop
American Airlines Logo
6:35 pm - 11:59 pmHRL-ORD
5h 24m1 stop
$269American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
4:20 pm - 9:30 pmORD-HRL
5h 10m1 stop
Southwest Logo
7:25 am - 3:20 pmHRL-ORD
7h 55m1 stop
$278Southwest
Find Deal
Mon, Aug 18 - Tue, Aug 26
United Airlines Logo
8:54 am - 4:06 pmORD-HRL
7h 12m1 stop
United Airlines Logo
5:20 pm - 12:14 amHRL-ORD
6h 54m1 stop
$293United Airlines
Find Deal
Wed, Dec 31 - Mon, Jan 5
Southwest Logo
4:20 pm - 9:30 pmORD-HRL
5h 10m1 stop
Southwest Logo
11:15 am - 9:30 pmHRL-ORD
10h 15m2 stops
$313Southwest
Find Deal
Mon, Aug 18 - Tue, Aug 26
Southwest Logo
4:20 pm - 9:25 pmORD-HRL
5h 05m1 stop
Southwest Logo
7:25 am - 2:25 pmHRL-ORD
7h 00m1 stop
$319Southwest
Find Deal
Wed, Aug 13 - Sat, Aug 16
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
$362Sun Country Air
Find Deal
Wed, Dec 31 - Sun, Jan 4
Southwest Logo
7:30 am - 2:55 pmORD-HRL
7h 25m2 stops
Southwest Logo
7:25 am - 2:25 pmHRL-ORD
7h 00m1 stop
$363Southwest
Find Deal
Wed, Aug 13 - Sat, Aug 16
United Airlines Logo
5:50 pm - 11:18 pmORD-HRL
5h 28m1 stop
United Airlines Logo
5:17 pm - 11:45 amHRL-ORD
18h 28m2 stops
$370United Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Logo
10:18 am - 10:53 amORD-HRL
24h 35m2 stops
Logo
11:47 am - 9:44 amHRL-ORD
21h 57m3 stops
$777
Find Deal
Wed, Dec 31 - Mon, Jan 5

American Airlines flights from Chicago to Harlingen, Texas

Our best American Airlines deals on Chicago to Harlingen, Texas flight tickets
American Airlines
Sep 26
ORD6:00 amChicago O'Hare Intl
8h 19m
1 stop
HRL2:19 pmHarlingen Valley Intl
Sep 29
HRL6:35 pmHarlingen Valley Intl
5h 24m
1 stop
ORD11:59 pmChicago O'Hare Intl
$247
Find similar
American Airlines
Sep 26
ORD6:00 amChicago O'Hare Intl
8h 19m
1 stop
HRL2:19 pmHarlingen Valley Intl
Sep 29
HRL6:35 pmHarlingen Valley Intl
5h 24m
1 stop
ORD11:59 pmChicago O'Hare Intl
$269
Find similar
American Airlines
Oct 9
ORD10:26 amChicago O'Hare Intl
7h 24m
1 stop
HRL5:50 pmHarlingen Valley Intl
Oct 12
HRL6:20 pmHarlingen Valley Intl
5h 33m
1 stop
ORD11:53 pmChicago O'Hare Intl
$393
Find similar

United Airlines flights from Chicago to Harlingen, Texas

Our best United Airlines deals on Chicago to Harlingen, Texas flight tickets
United Airlines
Dec 31
ORD8:54 amChicago O'Hare Intl
7h 12m
1 stop
HRL4:06 pmHarlingen Valley Intl
Jan 5
HRL5:20 pmHarlingen Valley Intl
6h 54m
1 stop
ORD12:14 amChicago O'Hare Intl
$293
Find similar
United Airlines
Sep 26
ORD5:50 pmChicago O'Hare Intl
5h 28m
1 stop
HRL11:18 pmHarlingen Valley Intl
Sep 29
HRL5:17 pmHarlingen Valley Intl
18h 28m
2 stops
ORD11:45 amChicago O'Hare Intl
$370
Find similar
United Airlines
Aug 12
ORD12:45 pmChicago O'Hare Intl
6h 50m
1 stop
HRL7:35 pmHarlingen Valley Intl
Aug 16
HRL5:15 pmHarlingen Valley Intl
5h 57m
1 stop
ORD11:12 pmChicago O'Hare Intl
$378
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 July 31, 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

Fri 9/26

6:00 am-2:19 pm

1 stop8h 19m

Harlingen Valley Intl

Mon 9/29

6:35 pm-11:59 pm

1 stop5h 24m

$247

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 9/26

6:00 am-2:19 pm

1 stop8h 19m

Harlingen Valley Intl

Mon 9/29

6:35 pm-11:59 pm

1 stop5h 24m

$269

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 8/18

4:20 pm-9:30 pm

1 stop5h 10m

Harlingen Valley Intl

Tue 8/26

7:25 am-3:20 pm

1 stop7h 55m

$278

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 12/31

8:54 am-4:06 pm

1 stop7h 12m

Harlingen Valley Intl

Mon 1/5

5:20 pm-12:14 am

1 stop6h 54m

$293

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 8/18

4:20 pm-9:30 pm

1 stop5h 10m

Harlingen Valley Intl

Tue 8/26

11:15 am-9:30 pm

2 stops10h 15m

$313

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 8/13

4:20 pm-9:25 pm

1 stop5h 05m

Harlingen Valley Intl

Sat 8/16

7:25 am-2:25 pm

1 stop7h 00m

$319

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

$362

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 8/13

7:30 am-2:55 pm

2 stops7h 25m

Harlingen Valley Intl

Sat 8/16

7:25 am-2:25 pm

1 stop7h 00m

$363

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 9/26

5:50 pm-11:18 pm

1 stop5h 28m

Harlingen Valley Intl

Mon 9/29

5:17 pm-11:45 am

2 stops18h 28m

$370

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 12/31

10:18 am-10:53 am

2 stops24h 35m

Harlingen Valley Intl

Mon 1/5

11:47 am-9:44 am

3 stops21h 57m

$777

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 typical price of a round-trip flight between Chicago and Harlingen, Texas?

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

The month of September is, on average, the cheapest month to fly to Harlingen, Texas from Chicago, with most prices found around $248. If you are unable to visit Harlingen, Texas during the month of September, then departing from Chicago during the month April is also very affordable. Most momondo users find prices during this month for around $273.

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 $419.

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 are 1 cabin classes 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

Best Price Found

$131

Fastest flight time

5h 05m

Direct flights

None

Airports in Harlingen, Texas

1 airport
The best one-way flight to Harlingen, Texas from Chicago in the past 72 hours is $131. The best round-trip flight deal from Chicago to Harlingen, Texas found on momondo in the last 72 hours is $247.
The fastest flight from Chicago to Harlingen, Texas takes 5h 05m
There are no direct flights from Chicago to Harlingen, Texas. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Harlingen Valley Intl Airport.
There is 1 airport near Harlingen, Texas: Harlingen Valley Intl (HRL)
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
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
10,000 reviews
Search American 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.

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