HRL - ORD

$210 Find Cheap Flights from Harlingen to Chicago O'Hare Airport

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Harlingen to O'Hare Intl departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Harlingen to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Harlingen to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Harlingen to O'Hare Intl (HRL-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Harlingen to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Harlingen to O'Hare Intl

Fri, Oct 24 - Mon, Oct 27
Southwest Logo
10:45 am - 9:30 pmHRL-ORD
10h 45m1 stop
Southwest Logo
4:20 pm - 11:30 pmORD-HRL
7h 10m2 stops
$210Southwest
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Fri, Oct 24 - Mon, Oct 27
Delta Logo
3:39 pm - 9:19 pmHRL-ORD
5h 40m1 stop
Delta Logo
8:57 am - 2:43 pmORD-HRL
5h 46m1 stop
$237Delta
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Tue, Oct 14 - Tue, Oct 21
Southwest Logo
10:40 am - 9:30 pmHRL-ORD
10h 50m1 stop
Southwest Logo
4:20 pm - 9:40 pmORD-HRL
5h 20m1 stop
$247Southwest
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Tue, Oct 28 - Wed, Nov 5
American Airlines Logo
6:37 pm - 11:42 pmHRL-ORD
5h 05m1 stop
American Airlines Logo
8:10 am - 3:32 pmORD-HRL
7h 22m1 stop
$251American Airlines
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Fri, Nov 14 - Mon, Nov 17
American Airlines Logo
6:40 pm - 11:37 pmHRL-ORD
4h 57m1 stop
American Airlines Logo
7:25 am - 3:32 pmORD-HRL
8h 07m1 stop
$269American Airlines
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Mon, Dec 29 - Sun, Jan 4
Sun Country Air Logo
11:13 am - 6:38 pmHRL-ORD
7h 25m1 stop
Sun Country Air Logo
7:50 pm - 10:47 amORD-HRL
14h 57m1 stop
$292Sun Country Air
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Mon, Oct 13 - Mon, Oct 20
United Airlines Logo
5:17 pm - 12:14 amHRL-ORD
6h 57m1 stop
United Airlines Logo
4:50 pm - 11:18 pmORD-HRL
6h 28m1 stop
$369United Airlines
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Thu, Dec 11 - Fri, Dec 19
Sun Country Air Logo
11:28 am - 10:51 amHRL-ORD
23h 23m1 stop
Sun Country Air Logo
7:38 pm - 10:02 amORD-HRL
14h 24m1 stop
$375Sun Country Air
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Thu, Nov 13 - Mon, Nov 17
United Airlines Logo
5:00 pm - 12:15 amHRL-ORD
7h 15m1 stop
United Airlines Logo
5:52 pm - 10:59 amORD-HRL
17h 07m2 stops
$426United Airlines
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Mon, Dec 29 - Sun, Jan 4
Multiple Airlines Logo
11:13 am - 6:25 amHRL-ORD
19h 12m2 stops
Multiple Airlines Logo
7:50 pm - 10:47 amORD-HRL
14h 57m1 stop
$480Multiple Airlines
Find Deal

Everything you should know

Top airlines
Southwest
Cheapest • from $210 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
March
Cheapest • 32% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$210
Typical prices: $252-332
Southwest
Fri 10/24Mon 10/27
HRL - ORD • 1 stop
Cheapest one-way
United Airlines
Tue 9/16
HRL - ORD • Non-stop
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We hope you love your trip to O'Hare Intl!
Booking Insights

KAYAK's insights & trends for Harlingen to O'Hare Intl flights

Get data-powered insights and trends into flights from Harlingen to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Harlingen to Chicago O'Hare Airport?

The average price of all round-trip flights from Harlingen to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago O'Hare Airport on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Harlingen to Chicago O'Hare Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Harlingen to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Harlingen to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Harlingen to Chicago O'Hare Intl Airport is March, where tickets cost $236 (return) on average. On the other hand, the most expensive months are April and May, where the average cost of round-trip tickets is $466 and $453 respectively.

Good to know

Low seasonMarch
Cheapest flight$210
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Harlingen to Chicago O'Hare Airport

When to book flights from Harlingen to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Harlingen to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Harlingen to Chicago O'Hare Airport flights

  • What is the cheapest flight from Harlingen to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Harlingen to Chicago O'Hare Intl Airport was $210 for a round-trip ticket.

  • Do I need a passport to fly between Harlingen and Chicago O'Hare Airport?

    No, a passport isn't needed to fly from Harlingen to Chicago O'Hare Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Harlingen to Chicago O'Hare Airport?

    Harlingen airport is called Harlingen Valley Intl and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Harlingen to Chicago O'Hare Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Harlingen to Chicago O'Hare Airport?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Harlingen and Chicago O'Hare Airport, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Harlingen to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Harlingen to Chicago are Southwest and United Airlines. With an average price for the route of $319 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $393 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Harlingen to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Harlingen to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Harlingen to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Harlingen is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Harlingen to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back to Harlingen with another airline. Booking your flights between Harlingen and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Harlingen to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport from Harlingen up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Harlingen to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Harlingen to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Harlingen to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Everything you need to know for your flight from Harlingen to O'Hare Intl

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