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Cheap flights from Harlingen to Chicago from $109

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 to Chicago departing on 11/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Harlingen to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:05 am - 11:20 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 15m1 stop Houston George Bush Intcntl
United Airlines Logo
6:30 am - 1:24 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 54m1 stop Houston George Bush Intcntl
$217United Airlines
Tue, Sep 15 - Tue, Sep 22
American Airlines Logo
6:43 pm - 12:18 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 35m1 stop Dallas/Fort Worth
American Airlines Logo
3:54 pm - 10:54 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 00m1 stop Dallas/Fort Worth
$229American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:08 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
5h 08m1 stop Dallas/Fort Worth
$270American Airlines
Tue, Oct 13 - Tue, Oct 27
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
12:10 pm - 6:12 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 02m1 stop Dallas/Fort Worth
$277American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
6:43 pm - 12:18 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 35m1 stop Dallas/Fort Worth
American Airlines Logo
3:54 pm - 10:54 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 00m1 stop Dallas/Fort Worth
$290American Airlines
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
1:59 pm - 8:05 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 06m1 stop Houston George Bush Intcntl
United Airlines Logo
12:47 pm - 7:39 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
6h 52m1 stop Houston George Bush Intcntl
$307United Airlines
Sat, Sep 12 - Sat, Sep 19
American Airlines Logo
6:42 pm - 11:59 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 17m1 stop Dallas/Fort Worth
American Airlines Logo
6:55 am - 2:16 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 21m1 stop Dallas/Fort Worth
$311American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
5:28 pm - 12:14 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
6h 46m1 stop Dallas/Fort Worth
American Airlines Logo
9:40 am - 4:58 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
7h 18m1 stop Dallas/Fort Worth
$311American Airlines
Tue, Sep 15 - Tue, Sep 22
American Airlines Logo
5:51 am - 11:09 amHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
5h 18m1 stop Dallas/Fort Worth
American Airlines Logo
12:09 pm - 4:58 pmORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
4h 49m1 stop Dallas/Fort Worth
$311American Airlines
Tue, Sep 15 - Tue, Sep 22
American Airlines Logo
10:45 am - 6:25 pmHRL  Harlingen Valley Intl-ORD Chicago O'Hare Intl
7h 40m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 9:58 amORD  Chicago O'Hare Intl-HRL Harlingen Valley Intl
4h 58m1 stop Dallas/Fort Worth
$325American Airlines
Tue, Sep 22 - Mon, Sep 28

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American Airlines flights from Harlingen to Chicago

Our best American Airlines deals on Harlingen to Chicago flight tickets
American Airlines
Sep 1
HRL6:43 pmHarlingen Valley Intl
5h 35m
1 stop
ORD12:18 amChicago O'Hare Intl
Sep 5
ORD3:54 pmChicago O'Hare Intl
7h 00m
1 stop
HRL10:54 pmHarlingen Valley Intl
$229
American Airlines
Oct 13
HRL6:42 pmHarlingen Valley Intl
5h 17m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 27
ORD5:00 amChicago O'Hare Intl
5h 08m
1 stop
HRL10:08 amHarlingen Valley Intl
$270
American Airlines
Oct 10
HRL6:42 pmHarlingen Valley Intl
5h 17m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 17
ORD12:10 pmChicago O'Hare Intl
6h 02m
1 stop
HRL6:12 pmHarlingen Valley Intl
$277

United Airlines flights from Harlingen to Chicago

Our best United Airlines deals on Harlingen to Chicago flight tickets
United Airlines
Sep 15
HRL5:05 amHarlingen Valley Intl
6h 15m
1 stop
ORD11:20 amChicago O'Hare Intl
Sep 22
ORD6:30 amChicago O'Hare Intl
6h 54m
1 stop
HRL1:24 pmHarlingen Valley Intl
$217
United Airlines
Sep 12
HRL1:59 pmHarlingen Valley Intl
6h 06m
1 stop
ORD8:05 pmChicago O'Hare Intl
Sep 19
ORD12:47 pmChicago O'Hare Intl
6h 52m
1 stop
HRL7:39 pmHarlingen Valley Intl
$307
United Airlines
Aug 18
HRL1:59 pmHarlingen Valley Intl
6h 06m
1 stop
ORD8:05 pmChicago O'Hare Intl
Aug 25
ORD10:40 amChicago O'Hare Intl
5h 19m
1 stop
HRL3:59 pmHarlingen Valley Intl
$369

momondo Fare Finder

 
Customize your flight search to find flights from Harlingen to Chicago 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 16, 2026.
Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/15

5:05 am-11:20 am

1 stop6h 15m

Chicago O'Hare Intl

Tue 9/22

6:30 am-1:24 pm

1 stop6h 54m

$217

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/1

6:43 pm-12:18 am

1 stop5h 35m

Chicago O'Hare Intl

Sat 9/5

3:54 pm-10:54 pm

1 stop7h 00m

$229

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 10/13

6:42 pm-11:59 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 10/27

5:00 am-10:08 am

1 stop5h 08m

$270

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Sat 10/10

6:42 pm-11:59 pm

1 stop5h 17m

Chicago O'Hare Intl

Sat 10/17

12:10 pm-6:12 pm

1 stop6h 02m

$277

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/1

6:43 pm-12:18 am

1 stop5h 35m

Chicago O'Hare Intl

Sat 9/5

3:54 pm-10:54 pm

1 stop7h 00m

$290

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Sat 9/12

1:59 pm-8:05 pm

1 stop6h 06m

Chicago O'Hare Intl

Sat 9/19

12:47 pm-7:39 pm

1 stop6h 52m

$307

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Sat 10/10

6:42 pm-11:59 pm

1 stop5h 17m

Chicago O'Hare Intl

Sat 10/17

6:55 am-2:16 pm

1 stop7h 21m

$311

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/15

5:28 pm-12:14 am

1 stop6h 46m

Chicago O'Hare Intl

Tue 9/22

9:40 am-4:58 pm

1 stop7h 18m

$311
Quickest round-trip

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/15

5:51 am-11:09 am

1 stop5h 18m

Chicago O'Hare Intl

Tue 9/22

12:09 pm-4:58 pm

1 stop4h 49m

$311

HarlingenChicago

HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl

HRLORD

Harlingen Valley Intl

Tue 9/22

10:45 am-6:25 pm

1 stop7h 40m

Chicago O'Hare Intl

Mon 9/28

5:00 am-9:58 am

1 stop4h 58m

$325

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 to Chicago

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?

The month of May is, on average, the cheapest month to fly to Chicago from Harlingen, with most prices found around $298. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Harlingen to Chicago during September average around $324.

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

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

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

There is only 1 cabin class available to choose from on Harlingen to Chicago 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 Harlingen to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Harlingen to Chicago flight.

When to book flights from Harlingen to Chicago

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

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

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

Fastest flight time

6h 06m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Harlingen to Chicago takes 6h 06m
Direct flights go from Harlingen to Chicago on Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Harlingen there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Harlingen to Chicago

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

    The distance between Harlingen Valley Intl and Chicago is about 1224.6 mi. A reasonable flight in good conditions will take 6h 06m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Harlingen Valley Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Harlingen to Chicago

Compare and see reviews for airlines that fly from Harlingen to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $250Free CancellationRating
7.4
10,104 reviews
Search United Airlines flights
American AirlinesPriceFrom $288Free CancellationRating
7.1
11,950 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Harlingen.

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

All flight searches from Harlingen to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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?

Price alerts on flights to Chicago from Harlingen are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport