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Cheap flights from Chicago to Harlingen from $104

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 9/10. 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
1 adult, Economy, 0 bags

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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 - 9:58 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
4h 58m1 stop Dallas/Fort Worth
American Airlines Logo
2:46 pm - 11:00 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
8h 14m1 stop Dallas/Fort Worth
$270American Airlines
Tue, Sep 29 - Wed, Oct 7
American Airlines Logo
3:50 pm - 10:50 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 00m1 stop Dallas/Fort Worth
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
$272American Airlines
Mon, Oct 5 - Mon, Oct 12
United Airlines Logo
8:45 am - 3:59 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 14m1 stop Houston George Bush Intcntl
United Airlines Logo
5:05 am - 11:16 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 11m1 stop Houston George Bush Intcntl
$307United Airlines
Tue, Sep 29 - Sat, Oct 3
American Airlines Logo
5:00 am - 9:58 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
4h 58m1 stop Dallas/Fort Worth
American Airlines Logo
5:51 am - 11:09 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 18m1 stop Dallas/Fort Worth
$311American Airlines
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
3:00 pm - 10:48 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 48m1 stop Dallas/Fort Worth
American Airlines Logo
2:46 pm - 10:10 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
7h 24m1 stop Dallas/Fort Worth
$311American Airlines
Tue, Sep 29 - Wed, Oct 7
Delta Logo
6:30 am - 1:32 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 02m1 stop Minneapolis St Paul
Delta Logo
2:30 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
9h 29m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$316Delta
Tue, Dec 1 - Tue, Dec 8
United Airlines Logo
5:30 pm - 10:48 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 18m1 stop Houston George Bush Intcntl
United Airlines Logo
5:16 pm - 12:15 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 59m1 stop Houston George Bush Intcntl
$325United Airlines
Tue, Nov 17 - Thu, Dec 3
United Airlines Logo
4:07 pm - 10:48 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 41m1 stop Houston George Bush Intcntl
United Airlines Logo
5:05 am - 11:17 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 12m1 stop Houston George Bush Intcntl
$325United Airlines
Sat, Nov 7 - Sun, Nov 8
Delta Logo
6:30 am - 1:32 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 02m1 stop Minneapolis St Paul
Delta Logo
2:30 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
9h 29m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$330Delta
Wed, Dec 2 - Wed, Dec 9
Delta Logo
6:20 am - 1:23 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 03m1 stop Minneapolis St Paul
Delta Logo
2:13 pm - 11:57 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
9h 44m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$330Delta
Sat, Nov 7 - Sun, Nov 8

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United Airlines flights from Chicago to Harlingen

Our best United Airlines deals on Chicago to Harlingen flight tickets
United Airlines
Sep 29
ORD8:45 amChicago O'Hare Intl
7h 14m
1 stop
HRL3:59 pmHarlingen Valley Intl
Oct 3
HRL5:05 amHarlingen Valley Intl
6h 11m
1 stop
ORD11:16 amChicago O'Hare Intl
$307
United Airlines
Nov 7
ORD4:07 pmChicago O'Hare Intl
6h 41m
1 stop
HRL10:48 pmHarlingen Valley Intl
Nov 8
HRL5:05 amHarlingen Valley Intl
6h 12m
1 stop
ORD11:17 amChicago O'Hare Intl
$325
United Airlines
Sep 11
ORD4:11 pmChicago O'Hare Intl
5h 41m
1 stop
HRL9:52 pmHarlingen Valley Intl
Sep 14
HRL5:18 pmHarlingen Valley Intl
6h 09m
1 stop
ORD11:27 pmChicago O'Hare Intl
$336

Delta flights from Chicago to Harlingen

Our best Delta deals on Chicago to Harlingen flight tickets
Delta
Dec 1
ORD6:30 amChicago O'Hare Intl
7h 02m
1 stop
HRL1:32 pmHarlingen Valley Intl
Dec 8
HRL2:30 pmHarlingen Valley Intl
9h 29m
2 stops
ORD11:59 pmChicago O'Hare Intl
$316
Delta
Nov 7
ORD6:20 amChicago O'Hare Intl
7h 03m
1 stop
HRL1:23 pmHarlingen Valley Intl
Nov 8
HRL2:13 pmHarlingen Valley Intl
9h 44m
2 stops
ORD11:57 pmChicago O'Hare Intl
$330
Delta
Nov 6
ORD6:20 amChicago O'Hare Intl
7h 03m
1 stop
HRL1:23 pmHarlingen Valley Intl
Nov 8
HRL2:13 pmHarlingen Valley Intl
9h 44m
2 stops
ORD11:57 pmChicago O'Hare Intl
$344

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 August 18, 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 Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 9/29

5:00 am-9:58 am

1 stop4h 58m

Harlingen Valley Intl

Wed 10/7

2:46 pm-11:00 pm

1 stop8h 14m

$270

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Mon 10/5

3:50 pm-10:50 pm

1 stop7h 00m

Harlingen Valley Intl

Mon 10/12

6:42 pm-11:59 pm

1 stop5h 17m

$272

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 9/29

8:45 am-3:59 pm

1 stop7h 14m

Harlingen Valley Intl

Sat 10/3

5:05 am-11:16 am

1 stop6h 11m

$307
Quickest round-trip

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 9/22

5:00 am-9:58 am

1 stop4h 58m

Harlingen Valley Intl

Sat 9/26

5:51 am-11:09 am

1 stop5h 18m

$311

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 9/29

3:00 pm-10:48 pm

1 stop7h 48m

Harlingen Valley Intl

Wed 10/7

2:46 pm-10:10 pm

1 stop7h 24m

$311

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 12/1

6:30 am-1:32 pm

1 stop7h 02m

Harlingen Valley Intl

Tue 12/8

2:30 pm-11:59 pm

2 stops9h 29m

$316

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Tue 11/17

5:30 pm-10:48 pm

1 stop5h 18m

Harlingen Valley Intl

Thu 12/3

5:16 pm-12:15 am

1 stop6h 59m

$325

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Sat 11/7

4:07 pm-10:48 pm

1 stop6h 41m

Harlingen Valley Intl

Sun 11/8

5:05 am-11:17 am

1 stop6h 12m

$325

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Wed 12/2

6:30 am-1:32 pm

1 stop7h 02m

Harlingen Valley Intl

Wed 12/9

2:30 pm-11:59 pm

2 stops9h 29m

$330

ChicagoHarlingen

ORD Chicago O'Hare Intl - HRL Harlingen Valley Intl

ORDHRL

Chicago O'Hare Intl

Sat 11/7

6:20 am-1:23 pm

1 stop7h 03m

Harlingen Valley Intl

Sun 11/8

2:13 pm-11:57 pm

2 stops9h 44m

$330

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

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?

Prices are currently low for flights on this route.

Typical prices usually range from $265 to $272.
The lowest price recently found on this route was $217.

What is the cheapest month to fly to Harlingen?

If you aren’t able to travel during the month of August, then book flights to Harlingen from Chicago during November instead. Flights to Harlingen in November, while not as cheap as those in August, still average around $298.

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 flights?

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

Can stopping save me money on Chicago to Harlingen flights?

You could potentially save up to 18% on your flight if you consider stops on a Chicago to Harlingen flight.

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

Best Price Found

$104

Fastest flight time

5h 04m

Direct flights

Sun

Airports in Harlingen

1 airport
The best one-way flight to Harlingen from Chicago in the past 72 hours is $104. The best round-trip flight deal from Chicago to Harlingen found on momondo in the last 72 hours is $270.
The fastest flight from Chicago to Harlingen takes 5h 04m
Direct flights go from Chicago to Harlingen on Sunday. There are no airlines offering direct flights.
There is 1 airport in Harlingen. From Chicago there are direct flights to Harlingen Valley Intl (HRL).
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 04m 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
4,219 reviews
Search Southwest flights
American AirlinesPriceFrom $233Free CancellationRating
7.1
11,957 reviews
Search American Airlines flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
10,102 reviews
Search United Airlines flights

  • Southwest Flights From Chicago to Harlingen

    Southwest flight deals from Chicago to Harlingen start from $216 round-trip. Over the 3 Southwest flights for this route in a normal week, average airfare is usually $348 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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