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Cheap flights from Harlingen, Texas to Chicago from $86

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 9/24. 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

Southwest Logo
7:25 am - 3:20 pmHRL-ORD
7h 55m1 stop
Southwest Logo
4:20 pm - 9:25 pmORD-HRL
5h 05m1 stop
$171Southwest
Find Deal
Tue, Sep 9 - Tue, Sep 16
American Airlines Logo
6:35 pm - 11:59 pmHRL-ORD
5h 24m1 stop
American Airlines Logo
6:00 am - 2:19 pmORD-HRL
8h 19m1 stop
$181American Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
American Airlines Logo
5:45 am - 11:00 amHRL-ORD
5h 15m1 stop
American Airlines Logo
3:08 pm - 10:57 pmORD-HRL
7h 49m1 stop
$196American Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
Southwest Logo
2:10 pm - 9:30 pmHRL-ORD
7h 20m2 stops
Southwest Logo
7:30 am - 1:35 pmORD-HRL
6h 05m1 stop
$205Southwest
Find Deal
Tue, Sep 9 - Tue, Sep 16
American Airlines Logo
6:19 pm - 11:52 pmHRL-ORD
5h 33m1 stop
American Airlines Logo
8:25 am - 2:19 pmORD-HRL
5h 54m1 stop
$214American Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27
Southwest Logo
7:00 am - 1:05 pmHRL-ORD
6h 05m1 stop
Southwest Logo
3:10 pm - 11:05 pmORD-HRL
7h 55m1 stop
$225Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
American Airlines Logo
6:35 pm - 11:59 pmHRL-ORD
5h 24m1 stop
American Airlines Logo
4:12 pm - 10:57 pmORD-HRL
6h 45m1 stop
$229American Airlines
Find Deal
Mon, Sep 29 - Tue, Sep 30
United Airlines Logo
5:00 am - 10:13 amHRL-ORD
5h 13m1 stop
United Airlines Logo
7:15 am - 9:52 pmORD-HRL
14h 37m2 stops
$356United Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
United Airlines Logo
5:00 am - 5:10 pmHRL-ORD
12h 10m2 stops
United Airlines Logo
4:50 pm - 9:52 pmORD-HRL
5h 02m1 stop
$358United Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
United Airlines Logo
5:00 am - 6:37 pmHRL-ORD
13h 37m2 stops
United Airlines Logo
10:35 am - 4:13 pmORD-HRL
5h 38m1 stop
$360United Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27

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 9
HRL5:00 amHarlingen Valley Intl
5h 13m
1 stop
ORD10:13 amChicago O'Hare Intl
Sep 16
ORD7:15 amChicago O'Hare Intl
14h 37m
2 stops
HRL9:52 pmHarlingen Valley Intl
$356
Find similar
United Airlines
Sep 9
HRL5:00 amHarlingen Valley Intl
12h 10m
2 stops
ORD5:10 pmChicago O'Hare Intl
Sep 16
ORD4:50 pmChicago O'Hare Intl
5h 02m
1 stop
HRL9:52 pmHarlingen Valley Intl
$358
Find similar
United Airlines
Sep 25
HRL5:00 amHarlingen Valley Intl
13h 37m
2 stops
ORD6:37 pmChicago O'Hare Intl
Sep 27
ORD10:35 amChicago O'Hare Intl
5h 38m
1 stop
HRL4:13 pmHarlingen Valley Intl
$360
Find similar

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

Our best American Airlines deals on Harlingen, Texas to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 9
HRL6:35 pmHarlingen Valley Intl
5h 24m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 16
ORD6:00 amChicago O'Hare Intl
8h 19m
1 stop
HRL2:19 pmHarlingen Valley Intl
$181
Find similar
American Airlines
Sep 9
HRL5:45 amHarlingen Valley Intl
5h 15m
1 stop
ORD11:00 amChicago O'Hare Intl
Sep 16
ORD3:08 pmChicago O'Hare Intl
7h 49m
1 stop
HRL10:57 pmHarlingen Valley Intl
$196
Find similar
American Airlines
Sep 25
HRL6:19 pmHarlingen Valley Intl
5h 33m
1 stop
ORD11:52 pmChicago O'Hare Intl
Sep 27
ORD8:25 amChicago O'Hare Intl
5h 54m
1 stop
HRL2:19 pmHarlingen Valley Intl
$214
Find similar

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 August 7, 2025.
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

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

7:25 am-3:20 pm

1 stop7h 55m

Chicago O'Hare Intl

Tue 9/16

4:20 pm-9:25 pm

1 stop5h 05m

$171

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

6:35 pm-11:59 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 9/16

6:00 am-2:19 pm

1 stop8h 19m

$181

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

5:45 am-11:00 am

1 stop5h 15m

Chicago O'Hare Intl

Tue 9/16

3:08 pm-10:57 pm

1 stop7h 49m

$196

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

2:10 pm-9:30 pm

2 stops7h 20m

Chicago O'Hare Intl

Tue 9/16

7:30 am-1:35 pm

1 stop6h 05m

$205

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 9/25

6:19 pm-11:52 pm

1 stop5h 33m

Chicago O'Hare Intl

Sat 9/27

8:25 am-2:19 pm

1 stop5h 54m

$214

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 10/23

7:00 am-1:05 pm

1 stop6h 05m

Chicago O'Hare Intl

Sun 10/26

3:10 pm-11:05 pm

1 stop7h 55m

$225

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 9/29

6:35 pm-11:59 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 9/30

4:12 pm-10:57 pm

1 stop6h 45m

$229

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

5:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

Tue 9/16

7:15 am-9:52 pm

2 stops14h 37m

$356

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 9/9

5:00 am-5:10 pm

2 stops12h 10m

Chicago O'Hare Intl

Tue 9/16

4:50 pm-9:52 pm

1 stop5h 02m

$358

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 9/25

5:00 am-6:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Sat 9/27

10:35 am-4:13 pm

1 stop5h 38m

$360

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Harlingen, Texas averaging around $323.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $261. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Harlingen, Texas because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $676.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Harlingen, Texas in the evening is the least expensive time of day to depart. momondo users have found prices as low as $377 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $676. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 are 1 cabin classes 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

Best Price Found

$86

Fastest flight time

5h 13m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Harlingen, Texas in the past 72 hours is $86. The best round-trip flight deal from Harlingen, Texas to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $171.
The fastest flight from Harlingen, Texas to Chicago O'Hare Intl Airport takes 5h 13m
There are no direct flights from Harlingen, Texas to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Harlingen Valley Intl Airport - Chicago O'Hare Intl Airport.
Search flight deals

  • 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 13m 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
American AirlinesPriceFrom $217Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $267Free CancellationRating
8.0
4,247 reviews
Search Southwest flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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

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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