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Cheap flights from Harlingen, Texas to Chicago from $251

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Harlingen, Texas to Chicago departing on 12/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
American Airlines Logo
6:10 pm - 11:35 pmHRL-ORD
5h 25m1 stop
American Airlines Logo
7:15 am - 3:30 pmORD-HRL
8h 15m1 stop
$251American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:44 pm - 11:44 pmHRL-ORD
5h 00m1 stop
American Airlines Logo
5:05 am - 10:36 amORD-HRL
5h 31m1 stop
$260American Airlines
Find Deal
Tue, Jan 13 - Thu, Feb 5
Delta Logo
3:41 pm - 9:40 pmHRL-ORD
5h 59m1 stop
Delta Logo
6:00 am - 2:46 pmORD-HRL
8h 46m1 stop
$269Delta
Find Deal
Fri, Dec 5 - Fri, Dec 12
American Airlines Logo
6:10 pm - 11:35 pmHRL-ORD
5h 25m1 stop
American Airlines Logo
5:18 am - 11:40 amORD-HRL
6h 22m1 stop
$280American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:10 pm - 11:35 pmHRL-ORD
5h 25m1 stop
American Airlines Logo
5:18 am - 11:40 amORD-HRL
6h 22m1 stop
$289American Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
United Airlines Logo
5:20 pm - 10:37 pmHRL-ORD
5h 17m1 stop
United Airlines Logo
7:35 am - 4:06 pmORD-HRL
8h 31m1 stop
$305United Airlines
Find Deal
Tue, Dec 23 - Fri, Jan 2
Delta Logo
3:39 pm - 9:36 pmHRL-ORD
5h 57m1 stop
Delta Logo
6:00 am - 2:43 pmORD-HRL
8h 43m1 stop
$359Delta
Find Deal
Thu, Nov 20 - Sat, Nov 29
Delta Logo
3:39 pm - 9:36 pmHRL-ORD
5h 57m1 stop
Delta Logo
8:50 am - 2:43 pmORD-HRL
5h 53m1 stop
$374Delta
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
5:25 pm - 12:28 amHRL-ORD
7h 03m1 stop
United Airlines Logo
7:50 pm - 8:01 pmORD-HRL
24h 11m2 stops
$376United Airlines
Find Deal
Thu, Jan 15 - Tue, Jan 20
American Airlines Logo
5:40 am - 10:36 amHRL-ORD
4h 56m1 stop
American Airlines Logo
4:02 pm - 11:59 pmORD-HRL
7h 57m1 stop
$379American Airlines
Find Deal
Wed, Nov 26 - Sat, Nov 29

American Airlines flights from Harlingen, Texas to Chicago

Our best American Airlines deals on Harlingen, Texas to Chicago flight tickets
American Airlines
Dec 3
HRL6:10 pmHarlingen Valley Intl
5h 25m
1 stop
ORD11:35 pmChicago O'Hare Intl
Dec 10
ORD7:15 amChicago O'Hare Intl
8h 15m
1 stop
HRL3:30 pmHarlingen Valley Intl
$251
Find similar
American Airlines
Jan 15
HRL6:02 amHarlingen Valley Intl
5h 53m
1 stop
ORD11:55 amChicago O'Hare Intl
Jan 20
ORD3:23 pmChicago O'Hare Intl
7h 58m
1 stop
HRL11:21 pmHarlingen Valley Intl
$260
Find similar
American Airlines
Dec 3
HRL6:10 pmHarlingen Valley Intl
5h 25m
1 stop
ORD11:35 pmChicago O'Hare Intl
Dec 10
ORD5:18 amChicago O'Hare Intl
6h 22m
1 stop
HRL11:40 amHarlingen Valley Intl
$280
Find similar

Delta flights from Harlingen, Texas to Chicago

Our best Delta deals on Harlingen, Texas to Chicago flight tickets
Delta
Dec 5
HRL3:41 pmHarlingen Valley Intl
5h 59m
1 stop
ORD9:40 pmChicago O'Hare Intl
Dec 12
ORD6:00 amChicago O'Hare Intl
8h 46m
1 stop
HRL2:46 pmHarlingen Valley Intl
$269
Find similar
Delta
Nov 20
HRL3:39 pmHarlingen Valley Intl
5h 57m
1 stop
ORD9:36 pmChicago O'Hare Intl
Nov 29
ORD6:00 amChicago O'Hare Intl
8h 43m
1 stop
HRL2:43 pmHarlingen Valley Intl
$359
Find similar
Delta
Nov 26
HRL3:39 pmHarlingen Valley Intl
5h 57m
1 stop
ORD9:36 pmChicago O'Hare Intl
Nov 30
ORD8:50 amChicago O'Hare Intl
5h 53m
1 stop
HRL2:43 pmHarlingen Valley Intl
$374
Find similar

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 November 13, 2025.
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

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 12/3

6:10 pm-11:35 pm

1 stop5h 25m

Chicago O'Hare Intl

Wed 12/10

7:15 am-3:30 pm

1 stop8h 15m

$251

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 1/13

6:44 pm-11:44 pm

1 stop5h 00m

Chicago O'Hare Intl

Thu 2/5

5:05 am-10:36 am

1 stop5h 31m

$260

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 12/5

3:41 pm-9:40 pm

1 stop5h 59m

Chicago O'Hare Intl

Fri 12/12

6:00 am-2:46 pm

1 stop8h 46m

$269

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 12/3

6:10 pm-11:35 pm

1 stop5h 25m

Chicago O'Hare Intl

Wed 12/10

5:18 am-11:40 am

1 stop6h 22m

$280

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 12/12

6:10 pm-11:35 pm

1 stop5h 25m

Chicago O'Hare Intl

Sun 12/14

5:18 am-11:40 am

1 stop6h 22m

$289

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 12/23

5:20 pm-10:37 pm

1 stop5h 17m

Chicago O'Hare Intl

Fri 1/2

7:35 am-4:06 pm

1 stop8h 31m

$305

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 11/20

3:39 pm-9:36 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 11/29

6:00 am-2:43 pm

1 stop8h 43m

$359

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 11/26

3:39 pm-9:36 pm

1 stop5h 57m

Chicago O'Hare Intl

Sun 11/30

8:50 am-2:43 pm

1 stop5h 53m

$374

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 1/15

5:25 pm-12:28 am

1 stop7h 03m

Chicago O'Hare Intl

Tue 1/20

7:50 pm-8:01 pm

2 stops24h 11m

$376

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Wed 11/26

5:40 am-10:36 am

1 stop4h 56m

Chicago O'Hare Intl

Sat 11/29

4:02 pm-11:59 pm

1 stop7h 57m

$379

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 typical price of a round-trip flight between Harlingen, Texas and Chicago?

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $263. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Harlingen, Texas to Chicago for around $676.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Harlingen, Texas to Chicago during this time can be as low as $351. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $676.

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.

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

3h 09m

Direct flights

Sun

Airports in Chicago

1 airport
The fastest flight from Harlingen, Texas to Chicago takes 3h 09m
Direct flights go from Harlingen, Texas to Chicago on Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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 3h 09m.

  • 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
American AirlinesPriceFrom $217Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
9,017 reviews
Search United 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
Schererville
Valparaiso
Crown Point
Munster
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