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Cheap flights from Harlingen, Texas to Chicago 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 Harlingen, Texas to Chicago departing on 7/16. 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 Harlingen, Texas to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:15 am - 10:14 am
HRL
-
ORD
4h 59m
1 stop
United Airlines Logo
5:30 am - 1:14 pm
ORD
-
HRL
7h 44m
1 stop
$275United Airlines
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
United Airlines Logo
7:30 am - 1:30 pm
ORD
-
HRL
6h 00m
1 stop
$276United Airlines
Wed, May 20 - Sun, May 24
United Airlines Logo
5:18 pm - 11:15 pm
HRL
-
ORD
5h 57m
1 stop
United Airlines Logo
12:43 pm - 7:40 pm
ORD
-
HRL
6h 57m
1 stop
$277United Airlines
Wed, Apr 15 - Sat, Apr 18
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
$281Southwest
Mon, May 18 - Wed, May 20
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
Fri, Apr 24 - Tue, Apr 28
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
$297American Airlines
Fri, May 1 - Sun, May 3
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
$302Southwest
Mon, May 18 - Wed, May 20
United Airlines Logo
5:18 pm - 11:15 pm
HRL
-
ORD
5h 57m
1 stop
United Airlines Logo
2:10 pm - 8:00 pm
ORD
-
HRL
5h 50m
1 stop
$306United Airlines
Wed, Apr 15 - Wed, May 13
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
3:45 pm - 8:35 pm
ORD
-
HRL
4h 50m
1 stop
$307Southwest
Fri, May 1 - Fri, May 8
Southwest Logo
7:10 am - 1:15 pm
HRL
-
ORD
6h 05m
1 stop
Southwest Logo
11:55 am - 10:00 pm
ORD
-
HRL
10h 05m
2 stops
$311Southwest
Wed, Apr 15 - Wed, May 13

United Airlines flights from Harlingen, Texas to Chicago O'Hare Intl Airport

Our best United Airlines deals on Harlingen, Texas to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 16
HRL5:15 amHarlingen Valley Intl
4h 59m
1 stop
ORD10:14 amChicago O'Hare Intl
Sep 19
ORD5:30 amChicago O'Hare Intl
7h 44m
1 stop
HRL1:14 pmHarlingen Valley Intl
$275
United Airlines
May 20
HRL5:18 pmHarlingen Valley Intl
7h 27m
1 stop
ORD12:45 amChicago O'Hare Intl
May 24
ORD7:30 amChicago O'Hare Intl
6h 00m
1 stop
HRL1:30 pmHarlingen Valley Intl
$276
United Airlines
Apr 15
HRL5:18 pmHarlingen Valley Intl
5h 57m
1 stop
ORD11:15 pmChicago O'Hare Intl
Apr 19
ORD5:48 amChicago O'Hare Intl
5h 35m
1 stop
HRL11:23 amHarlingen Valley Intl
$277

Southwest flights from Harlingen, Texas to Chicago O'Hare Intl Airport

Our best Southwest deals on Harlingen, Texas to Chicago O'Hare Intl Airport flight tickets
Southwest
May 18
HRL6:55 amHarlingen Valley Intl
6h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
May 20
ORD11:55 amChicago O'Hare Intl
10h 05m
2 stops
HRL10:00 pmHarlingen Valley Intl
$281
Southwest
Apr 24
HRL6:55 amHarlingen Valley Intl
6h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
Apr 28
ORD11:55 amChicago O'Hare Intl
10h 05m
2 stops
HRL10:00 pmHarlingen Valley Intl
$282
Southwest
May 18
HRL6:55 amHarlingen Valley Intl
6h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
May 20
ORD11:55 amChicago O'Hare Intl
10h 05m
2 stops
HRL10:00 pmHarlingen Valley Intl
$302

momondo Fare Finder

 
Customize your flight search to find flights from Harlingen, Texas to Chicago O'Hare Intl Airport 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 April 4, 2026.
Use the filters below to find and compare flights from Harlingen, Texas to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 9/16

5:15 am-10:14 am

1 stop4h 59m

Chicago O'Hare Intl

Sat 9/19

5:30 am-1:14 pm

1 stop7h 44m

$275

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 5/20

5:18 pm-12:45 am

1 stop7h 27m

Chicago O'Hare Intl

Sun 5/24

7:30 am-1:30 pm

1 stop6h 00m

$276

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 4/15

5:18 pm-11:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 4/18

12:43 pm-7:40 pm

1 stop6h 57m

$277

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 5/18

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 5/20

11:55 am-10:00 pm

2 stops10h 05m

$281

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 4/24

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Tue 4/28

11:55 am-10:00 pm

2 stops10h 05m

$282

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 5/1

2:47 pm-10:45 pm

1 stop7h 58m

Chicago O'Hare Intl

Sun 5/3

5:00 am-10:17 am

1 stop5h 17m

$297

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 5/18

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 5/20

11:55 am-10:00 pm

2 stops10h 05m

$302

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 4/15

5:18 pm-11:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Wed 5/13

2:10 pm-8:00 pm

1 stop5h 50m

$306
Quickest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 5/1

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Fri 5/8

3:45 pm-8:35 pm

1 stop4h 50m

$307

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 4/15

7:10 am-1:15 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 5/13

11:55 am-10:00 pm

2 stops10h 05m

$311

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 Chicago from

How to get the cheapest flight ticket from Harlingen, Texas to Chicago O'Hare Intl Airport

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 Harlingen, Texas and Chicago O'Hare Intl Airport?

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

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

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

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

How have Harlingen, Texas to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Harlingen, Texas to Chicago O'Hare Intl Airport

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

Cheap Harlingen, Texas to Chicago O'Hare Intl Airport (HRL to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Harlingen, Texas to Chicago O'Hare Intl Airport

Fastest flight time

5h 57m

Direct flights

None
The fastest flight from Harlingen, Texas to Chicago O'Hare Intl Airport takes 5h 57m
There are no direct flights from Harlingen, Texas to Chicago O'Hare Intl Airport. There are no popular flight routes from Harlingen, Texas to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Harlingen, Texas to Chicago O'Hare Intl Airport

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

    A flight from Harlingen Valley Intl to Chicago O'Hare Intl will travel around 1223.5 mi. Typically, this will take 5h 57m by plane in normal conditions.

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

    Prices for flights from Harlingen Valley Intl Airport to Chicago O'Hare Intl Airport refresh daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Harlingen Valley Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Harlingen, Texas to Chicago O'Hare Intl Airport?

Best airlines flying from Harlingen, Texas to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Harlingen, Texas to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $250Free CancellationRating
7.4
9,542 reviews
Search United Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,343 reviews
Search Southwest flights
American AirlinesPriceFrom $259Free CancellationRating
7.1
11,559 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
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Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
South Holland

Why use momondo?

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

Finding the right flight to Chicago from Harlingen is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Chicago from Harlingen which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Harlingen to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Harlingen to Chicago 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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