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Cheap flights from Harlingen, Texas 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, Texas to Chicago departing on 9/30. 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

United Airlines Logo
5:17 pm - 10:37 pmHRL-ORD
5h 20m1 stop
United Airlines Logo
3:58 pm - 11:18 pmORD-HRL
7h 20m1 stop
$227United Airlines
Find Deal
Tue, Sep 30 - Thu, Oct 2
American Airlines Logo
6:19 pm - 11:52 pmHRL-ORD
5h 33m1 stop
American Airlines Logo
4:18 pm - 10:57 pmORD-HRL
6h 39m1 stop
$237American Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27
Southwest Logo
11:55 am - 9:30 pmHRL-ORD
9h 35m1 stop
Southwest Logo
4:20 pm - 10:35 pmORD-HRL
6h 15m1 stop
$242Southwest
Find Deal
Fri, Sep 26 - Fri, Oct 3
United Airlines Logo
5:17 pm - 12:14 amHRL-ORD
6h 57m1 stop
United Airlines Logo
2:20 pm - 7:41 pmORD-HRL
5h 21m1 stop
$257United Airlines
Find Deal
Fri, Sep 26 - Fri, Oct 3
American Airlines Logo
6:19 pm - 11:52 pmHRL-ORD
5h 33m1 stop
American Airlines Logo
4:18 pm - 10:57 pmORD-HRL
6h 39m1 stop
$259American Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27
Southwest Logo
7:30 am - 4:25 pmHRL-ORD
8h 55m1 stop
Southwest Logo
3:10 pm - 11:05 pmORD-HRL
7h 55m1 stop
$272Southwest
Find Deal
Tue, Oct 14 - Sun, Oct 26
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
$276American Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
Sun Country Air Logo
2:23 pm - 12:38 pmHRL-ORD
22h 15m1 stop
Sun Country Air Logo
8:00 am - 9:16 amORD-HRL
25h 16m1 stop
$295Sun Country Air
Find Deal
Thu, Oct 16 - Sun, Oct 19
Delta Logo
3:39 pm - 9:19 pmHRL-ORD
5h 40m1 stop
Delta Logo
6:08 am - 2:43 pmORD-HRL
8h 35m1 stop
$300Delta
Find Deal
Tue, Oct 14 - Sun, Oct 26
Delta Logo
3:39 pm - 9:19 pmHRL-ORD
5h 40m1 stop
Delta Logo
6:08 am - 2:43 pmORD-HRL
8h 35m1 stop
$414Delta
Find Deal
Sat, Oct 18 - Sun, Oct 26

United Airlines flights from Harlingen, Texas to Chicago

Our best United Airlines deals on Harlingen, Texas to Chicago flight tickets
United Airlines
Sep 30
HRL5:17 pmHarlingen Valley Intl
5h 20m
1 stop
ORD10:37 pmChicago O'Hare Intl
Oct 2
ORD3:58 pmChicago O'Hare Intl
7h 20m
1 stop
HRL11:18 pmHarlingen Valley Intl
$227
Find similar
United Airlines
Sep 26
HRL5:17 pmHarlingen Valley Intl
6h 57m
1 stop
ORD12:14 amChicago O'Hare Intl
Oct 3
ORD2:20 pmChicago O'Hare Intl
5h 21m
1 stop
HRL7:41 pmHarlingen Valley Intl
$257
Find similar
United Airlines
Feb 24
HRL5:15 amHarlingen Valley Intl
4h 52m
1 stop
ORD10:07 amChicago O'Hare Intl
Feb 25
ORD2:15 pmChicago O'Hare Intl
5h 14m
1 stop
HRL7:29 pmHarlingen Valley Intl
$297
Find similar

Southwest flights from Harlingen, Texas to Chicago

Our best Southwest deals on Harlingen, Texas to Chicago flight tickets
Southwest
Sep 6
HRL7:25 amHarlingen Valley Intl
7h 00m
1 stop
ORD2:25 pmChicago O'Hare Intl
Oct 6
ORD4:20 pmChicago O'Hare Intl
6h 15m
1 stop
HRL10:35 pmHarlingen Valley Intl
$223
Find similar
Southwest
Sep 26
HRL11:55 amHarlingen Valley Intl
9h 35m
1 stop
ORD9:30 pmChicago O'Hare Intl
Oct 3
ORD4:20 pmChicago O'Hare Intl
6h 15m
1 stop
HRL10:35 pmHarlingen Valley Intl
$242
Find similar
Southwest
Sep 3
HRL7:25 amHarlingen Valley Intl
7h 55m
1 stop
ORD3:20 pmChicago O'Hare Intl
Sep 10
ORD4:20 pmChicago O'Hare Intl
5h 05m
1 stop
HRL9:25 pmHarlingen Valley Intl
$264
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 August 28, 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

Tue 9/30

5:17 pm-10:37 pm

1 stop5h 20m

Chicago O'Hare Intl

Thu 10/2

3:58 pm-11:18 pm

1 stop7h 20m

$227

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

4:18 pm-10:57 pm

1 stop6h 39m

$237

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 9/26

11:55 am-9:30 pm

1 stop9h 35m

Chicago O'Hare Intl

Fri 10/3

4:20 pm-10:35 pm

1 stop6h 15m

$242

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Fri 9/26

5:17 pm-12:14 am

1 stop6h 57m

Chicago O'Hare Intl

Fri 10/3

2:20 pm-7:41 pm

1 stop5h 21m

$257

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

4:18 pm-10:57 pm

1 stop6h 39m

$259

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 10/14

7:30 am-4:25 pm

1 stop8h 55m

Chicago O'Hare Intl

Sun 10/26

3:10 pm-11:05 pm

1 stop7h 55m

$272

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

$276

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Thu 10/16

2:23 pm-12:38 pm

1 stop22h 15m

Chicago O'Hare Intl

Sun 10/19

8:00 am-9:16 am

1 stop25h 16m

$295

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Tue 10/14

3:39 pm-9:19 pm

1 stop5h 40m

Chicago O'Hare Intl

Sun 10/26

6:08 am-2:43 pm

1 stop8h 35m

$300

HarlingenChicago

HRL - ORD

HRLORD

Harlingen Valley Intl

Sat 10/18

3:39 pm-9:19 pm

1 stop5h 40m

Chicago O'Hare Intl

Sun 10/26

6:08 am-2:43 pm

1 stop8h 35m

$414

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

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 September is, on average, the cheapest month to fly to Chicago from Harlingen, Texas, with most prices found around $256. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Harlingen, Texas to Chicago during May average around $257.

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

Direct flights

None
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 4h 52m.

  • 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
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
8,944 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
Lansing
Portage
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