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Cheap flights from Harlingen to Chicago 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 Harlingen to Chicago departing on 7/8. 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

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.
American Airlines Logo
6:45 pm - 11:48 pm
HRL
-
ORD
5h 03m
1 stop
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
$276American Airlines
Tue, May 19 - Wed, May 27
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
3:45 pm - 8:55 pm
ORD
-
HRL
5h 10m
1 stop
$289Southwest
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
3:45 pm - 8:55 pm
ORD
-
HRL
5h 10m
1 stop
$290Southwest
Mon, Jun 1 - Wed, Jun 3
American Airlines Logo
6:45 pm - 11:48 pm
HRL
-
ORD
5h 03m
1 stop
American Airlines Logo
4:44 pm - 12:14 am
ORD
-
HRL
7h 30m
1 stop
$293American Airlines
Tue, May 19 - Sat, May 23
United Airlines Logo
5:20 pm - 11:15 pm
HRL
-
ORD
5h 55m
1 stop
United Airlines Logo
2:05 pm - 9:54 pm
ORD
-
HRL
7h 49m
1 stop
$301United Airlines
Sat, May 23 - Wed, May 27
Southwest Logo
12:45 pm - 9:55 pm
HRL
-
ORD
9h 10m
2 stops
Southwest Logo
11:55 am - 5:20 pm
ORD
-
HRL
5h 25m
1 stop
$336Southwest
Tue, May 19 - Wed, May 27
American Airlines Logo
4:57 pm - 11:37 pm
HRL
-
ORD
6h 40m
1 stop
American Airlines Logo
5:00 am - 10:13 am
ORD
-
HRL
5h 13m
1 stop
$341American Airlines
Fri, May 29 - Fri, Jun 5
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
$342Southwest
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
2:40 pm - 10:00 pm
ORD
-
HRL
7h 20m
2 stops
$343Southwest
Mon, Jun 1 - Wed, Jun 3
Delta Logo
2:00 pm - 7:34 pm
HRL
-
ORD
5h 34m
1 stop
Delta Logo
6:00 am - 1:31 pm
ORD
-
HRL
7h 31m
1 stop
$344Delta
Thu, Oct 8 - Sun, Oct 11

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American Airlines flights from Harlingen to Chicago

Our best American Airlines deals on Harlingen to Chicago flight tickets
American Airlines
May 19
HRL6:45 pmHarlingen Valley Intl
5h 03m
1 stop
ORD11:48 pmChicago O'Hare Intl
May 27
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
HRL10:13 amHarlingen Valley Intl
$276
American Airlines
May 19
HRL6:45 pmHarlingen Valley Intl
5h 03m
1 stop
ORD11:48 pmChicago O'Hare Intl
May 23
ORD4:44 pmChicago O'Hare Intl
7h 30m
1 stop
HRL12:14 amHarlingen Valley Intl
$293
American Airlines
May 29
HRL4:57 pmHarlingen Valley Intl
6h 40m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jun 5
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
HRL10:13 amHarlingen Valley Intl
$341

United Airlines flights from Harlingen to Chicago

Our best United Airlines deals on Harlingen to Chicago flight tickets
United Airlines
May 23
HRL5:20 pmHarlingen Valley Intl
5h 55m
1 stop
ORD11:15 pmChicago O'Hare Intl
May 27
ORD2:05 pmChicago O'Hare Intl
7h 49m
1 stop
HRL9:54 pmHarlingen Valley Intl
$301
United Airlines
May 6
HRL5:18 pmHarlingen Valley Intl
5h 57m
1 stop
ORD11:15 pmChicago O'Hare Intl
May 13
ORD2:05 pmChicago O'Hare Intl
5h 55m
1 stop
HRL8:00 pmHarlingen Valley Intl
$328
United Airlines
Aug 11
HRL2:00 pmHarlingen Valley Intl
7h 37m
1 stop
ORD9:37 pmChicago O'Hare Intl
Aug 12
ORD4:05 pmChicago O'Hare Intl
5h 39m
1 stop
HRL9:44 pmHarlingen Valley Intl
$351

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 May 3, 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
Quickest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 5/19

6:45 pm-11:48 pm

1 stop5h 03m

Chicago O'Hare Intl

Wed 5/27

5:00 am-10:13 am

1 stop5h 13m

$276

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 6/1

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 6/3

3:45 pm-8:55 pm

1 stop5h 10m

$289

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 6/1

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 6/3

3:45 pm-8:55 pm

1 stop5h 10m

$290

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 5/19

6:45 pm-11:48 pm

1 stop5h 03m

Chicago O'Hare Intl

Sat 5/23

4:44 pm-12:14 am

1 stop7h 30m

$293

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 5/23

5:20 pm-11:15 pm

1 stop5h 55m

Chicago O'Hare Intl

Wed 5/27

2:05 pm-9:54 pm

1 stop7h 49m

$301

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 5/19

12:45 pm-9:55 pm

2 stops9h 10m

Chicago O'Hare Intl

Wed 5/27

11:55 am-5:20 pm

1 stop5h 25m

$336

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 5/29

4:57 pm-11:37 pm

1 stop6h 40m

Chicago O'Hare Intl

Fri 6/5

5:00 am-10:13 am

1 stop5h 13m

$341

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 6/1

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 6/3

11:55 am-10:00 pm

2 stops10h 05m

$342

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 6/1

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 6/3

2:40 pm-10:00 pm

2 stops7h 20m

$343

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 10/8

2:00 pm-7:34 pm

1 stop5h 34m

Chicago O'Hare Intl

Sun 10/11

6:00 am-1:31 pm

1 stop7h 31m

$344

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 typical price of a round-trip flight between Harlingen and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Harlingen, with most prices found around $130. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Harlingen to Chicago during November average around $134.

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

Can stopping save me money on Harlingen to Chicago flights?

You could potentially save up to 37% on your flight if you consider stops on a Harlingen to Chicago flight.

How have Harlingen to Chicago flight prices changed over time?

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

4h 59m

Direct flights

None
The fastest flight from Harlingen to Chicago takes 4h 59m
There are no direct flights from Harlingen to Chicago. There are no popular flight routes from Harlingen to Chicago.
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 4h 59m.

  • 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
9,682 reviews
Search United Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,312 reviews
Search Southwest flights
American AirlinesPriceFrom $259Free CancellationRating
7.1
11,672 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
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