Cheap Flights from Chicago to Harlingen

Compare Chicago to Harlingen flight deals

Find the cheapest month or even day of the year to fly to Harlingen

Book the best Harlingen fare with no extra fees

Find the cheapest month to fly from Chicago to Harlingen

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Harlingen flights are currently cheapest in October.

Direct flights from Chicago to Harlingen

Chicago to Harlingen: Alternative routes

Compare routes from Chicago to Harlingen below. You may find an airport to fly into that's cheaper, faster, or easier than Harlingen.

Chicago to Harlingen: Flight information

The things to know before you go.
Cheapest flight foundRs38,485
Cheapest month to flyOctober
Average flight time3 hrs, 52 mins
Most popular airlineUnited
Average flights per week2

Finding cheap flights from Chicago to Harlingen: Frequently asked questions

The best price we found for a return flight from Chicago to Harlingen is Rs86,854. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 52 minutes is the average flight time from Chicago to Harlingen.
United and SkyWest Airlines fly direct from Chicago to Harlingen.
As of September 2025, there are 2 flights per week flying from Chicago to Harlingen.
The cheapest month to fly from Chicago to Harlingen is usually October.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Harlingen Airport on Thursday, 16 October 2025.
Yes – the average flight time is 3 hours and 52 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Harlingen but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Harlingen is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Harlingen is Southwest Airlines .

Travelling from Chicago to Valley International Airport (HRL): What you need to know

  • Kick off your journey at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to Valley International Airport (HRL) taking off from either of these.

  • Expect to be in the air for 3 hours 50 minutes. On average, that's the time it takes for a direct Chicago to Valley International Airport flight.

  • Harlingen (where Valley International Airport is located) and Chicago share the UTC-5 timezone. You'll have no time difference to factor in for your trip.

  • Leave enough time to catch your flight from Chicago to HRL. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Heading off during a peak time like a bank holiday? Expect longer queues at security and check-in. Give yourself extra leeway and arrive up to four hours before international flights and two hours ahead of domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can book a direct flight from Chicago to Valley International Airport (HRL) leaving from O'Hare International Airport (ORD).

  • You'll find a direct flight from Chicago to Valley International Airport with United Airlines. This leading airline operates departures from ORD.

  • The airline most travellers choose when flying between ORD and HRL is United Airlines.

  • The journey from central Chicago to ORD takes about 55 minutes by public transport. If you drive, ride-share or take a cab, you'll cover the 40 kilometres in 35 minutes or so, depending on traffic conditions.

  • Looking for a convenient hotel near O'Hare International Airport? If you're catching an early flight from Chicago to Valley International Airport, these stays will put you a quick hop from check-in:

  • 74.85% of flights that take off from O'Hare International Airport reach their destination on schedule.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • With public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 19 kilometres away, and making the journey by car will take approximately 20 minutes.

  • Flying out early in the morning? Think about checking in to one of these hotels near Chicago Midway International Airport the day before your Chicago to HRL flight:

  • 77.88% of flights out of Chicago Midway International Airport stick to their scheduled arrival time.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 137 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 25 minutes. If you're thinking about using public transport, you can expect a journey of around 4 hours 15 minutes.

  • Relax in bed for a little longer and still make your Chicago to Valley International Airport flight with plenty of time to spare. These accommodation options near Chicago Rockford International Airport make it a breeze to get to the terminal if you're jetting off early:

  • The on-time performance record of RFD is 76.19%. In simpler terms, that's how often flights from this airport arrive as planned.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Valley International Airport (HRL)

How to find the cheapest flights from Chicago to Valley International Airport (HRL)

  • Right now, Rs38,485 is the best price we've found for a one-way ticket from Chicago to Valley International Airport. The cheapest price for a return flight is Rs86,854. Remember fares may change due to availability at the time of booking.

  • Book one month before your departure date. Research into pricing trends suggests this is the ideal window for finding cheap flights from Chicago to HRL.

  • The best month for scoring cheap Chicago to Valley International Airport tickets is June. Use the 'Whole month' tool to compare prices, then choose the dates with the lowest fares.

  • You don't need to search every day to find out if fares have dropped when you set up a Price Alert. We'll notify you the moment there's a better deal on flight tickets from Chicago to HRL.

  • Nail down a great price on a flight from Chicago to Valley International Airport with the help of the filters. Choose your ideal departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best.'

The best time to fly from Chicago to Valley International Airport (HRL)

  • October is the most popular month for flights from Chicago to Valley International Airport (HRL). Plan your visit to Harlingen in April for a quieter experience.

  • The warmest month in Harlingen is August, with temperatures ranging between 25ºC and 37ºC. Lock in your Chicago to HRL flight ticket then if that's your idea of comfortable weather.

  • Look for cheap tickets from Chicago to Valley International Airport in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between 10ºC and 25ºC.

More about Harlingen

  • Once you've booked your flight from Chicago to Valley International Airport, find a hotel that keeps you close to what you want to see. Make one of these options your base for exploring Harlingen:

  • There are loads of terrific things to do in Harlingen when you're in the mood to sightsee. Start exploring at Harlingen Arts & Heritage Museum followed by Rio Grande Valley Birding Festival and Iwo Jima Memorial & Museum.

Explore more of the United States

  • Harlingen has loads to offer, but there are so many other corners of the United States just waiting to be discovered. About 177 kilometres north of Harlingen, a visit to Corpus Christi will fill your itinerary to the brim. Start with attractions like Texas State Aquarium, Bayfront Park and Corpus Christi Cathedral.

  • Laredo is another well-known destination in the United States and is around 225 kilometres north-west of Harlingen. No journey is complete without visiting San Francisco Javier Park, San Augustin Plaza and Fort McIntosh.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.