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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 4/17. 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 Harlingen, Texas to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
United Airlines Logo
5:48 am - 11:23 am
ORD
-
HRL
5h 35m
1 stop
$277United Airlines
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
6:55 am - 1:15 pm
HRL
-
ORD
6h 20m
1 stop
Southwest Logo
2:05 pm - 9:35 pm
ORD
-
HRL
7h 30m
2 stops
$282Southwest
Mon, Apr 27 - Sat, May 2
United Airlines Logo
5:18 pm - 12:45 am
HRL
-
ORD
7h 27m
1 stop
United Airlines Logo
4:03 pm - 9:59 pm
ORD
-
HRL
5h 56m
1 stop
$293United Airlines
Tue, Mar 31 - Sat, Apr 4
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
$297Southwest
Fri, May 1 - Fri, May 8
United Airlines Logo
5:18 pm - 11:15 pm
HRL
-
ORD
5h 57m
1 stop
United Airlines Logo
2:05 pm - 7:40 pm
ORD
-
HRL
5h 35m
1 stop
$301United Airlines
Sat, Apr 11 - Sat, Apr 18
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
$303United Airlines
Wed, May 6 - Sat, May 9
American Airlines Logo
2:47 pm - 9:13 pm
HRL
-
ORD
6h 26m
1 stop
American Airlines Logo
5:00 am - 10:17 am
ORD
-
HRL
5h 17m
1 stop
$307American Airlines
Wed, May 6 - Sat, May 9
Southwest Logo
6:55 am - 3:30 pm
HRL
-
ORD
8h 35m
2 stops
Southwest Logo
3:45 pm - 11:00 pm
ORD
-
HRL
7h 15m
1 stop
$322Southwest
Thu, Apr 23 - Sun, Apr 26
American Airlines Logo
2:47 pm - 10:00 pm
HRL
-
ORD
7h 13m
1 stop
American Airlines Logo
5:00 am - 10:17 am
ORD
-
HRL
5h 17m
1 stop
$328American Airlines
Sun, Apr 26 - Sat, May 2
Southwest Logo
6:50 am - 2:20 pm
HRL
-
ORD
7h 30m
1 stop
Southwest Logo
3:45 pm - 9:25 pm
ORD
-
HRL
5h 40m
1 stop
$337Southwest
Fri, Mar 27 - Tue, Mar 31

American Airlines flights from Harlingen, Texas to Chicago

Our best American Airlines deals on Harlingen, Texas to Chicago flight tickets
American Airlines
May 12
HRL6:45 pmHarlingen Valley Intl
5h 03m
1 stop
ORD11:48 pmChicago O'Hare Intl
May 19
ORD5:00 amChicago O'Hare Intl
5h 17m
1 stop
HRL10:17 amHarlingen Valley Intl
$284
American Airlines
May 6
HRL2:47 pmHarlingen Valley Intl
6h 26m
1 stop
ORD9:13 pmChicago O'Hare Intl
May 9
ORD5:00 amChicago O'Hare Intl
5h 17m
1 stop
HRL10:17 amHarlingen Valley Intl
$307
American Airlines
Apr 26
HRL2:47 pmHarlingen Valley Intl
7h 13m
1 stop
ORD10:00 pmChicago O'Hare Intl
May 2
ORD5:00 amChicago O'Hare Intl
5h 17m
1 stop
HRL10:17 amHarlingen Valley Intl
$328

Southwest flights from Harlingen, Texas to Chicago

Our best Southwest deals on Harlingen, Texas to Chicago flight tickets
Southwest
Apr 27
HRL6:55 amHarlingen Valley Intl
6h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
May 2
ORD2:05 pmChicago O'Hare Intl
7h 30m
2 stops
HRL9:35 pmHarlingen Valley Intl
$282
Southwest
May 1
HRL6:55 amHarlingen Valley Intl
6h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
May 8
ORD3:45 pmChicago O'Hare Intl
4h 50m
1 stop
HRL8:35 pmHarlingen Valley Intl
$297
Southwest
Apr 23
HRL6:55 amHarlingen Valley Intl
8h 35m
2 stops
ORD3:30 pmChicago O'Hare Intl
Apr 26
ORD3:45 pmChicago O'Hare Intl
7h 15m
1 stop
HRL11:00 pmHarlingen Valley Intl
$322

momondo Fare Finder

 
Customize your flight search to find flights from Harlingen, Texas 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 March 17, 2026.
Use the filters below to find and compare flights from Harlingen, Texas to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 4/23

5:18 pm-12:45 am

1 stop7h 27m

Chicago O'Hare Intl

Sun 4/26

5:48 am-11:23 am

1 stop5h 35m

$277

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Mon 4/27

6:55 am-1:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Sat 5/2

2:05 pm-9:35 pm

2 stops7h 30m

$282

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 3/31

5:18 pm-12:45 am

1 stop7h 27m

Chicago O'Hare Intl

Sat 4/4

4:03 pm-9:59 pm

1 stop5h 56m

$293
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

$297

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 4/11

5:18 pm-11:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 4/18

2:05 pm-7:40 pm

1 stop5h 35m

$301

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 5/6

5:18 pm-11:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 5/9

2:10 pm-8:00 pm

1 stop5h 50m

$303

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 5/6

2:47 pm-9:13 pm

1 stop6h 26m

Chicago O'Hare Intl

Sat 5/9

5:00 am-10:17 am

1 stop5h 17m

$307

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 4/23

6:55 am-3:30 pm

2 stops8h 35m

Chicago O'Hare Intl

Sun 4/26

3:45 pm-11:00 pm

1 stop7h 15m

$322

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sun 4/26

2:47 pm-10:00 pm

1 stop7h 13m

Chicago O'Hare Intl

Sat 5/2

5:00 am-10:17 am

1 stop5h 17m

$328

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 3/27

6:50 am-2:20 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 3/31

3:45 pm-9:25 pm

1 stop5h 40m

$337

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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

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, Texas, with most prices found around $257. If you’re not able to fly to Chicago in May, then August is your next best option. Flight prices from Harlingen, Texas to Chicago during August average around $278.

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 Valley Intl to Chicago flights?

There is only 1 cabin class available to choose from on Harlingen Valley Intl 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, Texas to Chicago flights?

You could potentially save up to 52% on your flight if you consider stops on a Harlingen, Texas to Chicago flight.

How have Harlingen, Texas to Chicago flight prices changed over time?

When to book flights from Harlingen, Texas to Chicago

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

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

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

Fastest flight time

6h 20m

Direct flights

None
The fastest flight from Harlingen, Texas to Chicago takes 6h 20m
There are no direct flights from Harlingen, Texas to Chicago. There are no popular flight routes from Harlingen, Texas to Chicago.
Search flight deals

  • 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 20m.

  • 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, Texas to Chicago?

Best airlines flying from Harlingen, Texas to Chicago

Compare and see reviews for airlines that fly from Harlingen, Texas to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $250Free CancellationRating
7.4
9,431 reviews
Search United Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,319 reviews
Search Southwest flights
American AirlinesPriceFrom $259Free CancellationRating
7.1
11,468 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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