Cheap flights from Harlingen to Chicago

Compare Harlingen to Chicago flight deals

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

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Flight deals from Harlingen to Chicago

Looking for a cheap last-minute deal or the best return flight from Harlingen Airport to Chicago? If you want to travel next month, return fares start from $342. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Harlingen to Chicago

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

Direct flights from Harlingen to Chicago

Harlingen to Chicago: Flight information

The things to know before you go.
Cheapest flight found$163
Cheapest month to flyJuly
Average flight time3 hrs, 30 mins
Most popular airlineQatar Airways
Average flights per week3

Finding cheap flights from Harlingen to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Harlingen to Chicago is $286. 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 30 minutes is the average flight time from Harlingen to Chicago.
Qatar Airways, Envoy Air and American Airlines fly direct from Harlingen to Chicago.
As of June 2026, there are 3 flights per week flying from Harlingen to Chicago.
The cheapest month to fly from Harlingen to Chicago is usually August.
If you're flying from Harlingen Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $286.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Harlingen Airport to Chicago on Saturday, 22 August 2026.
Yes – the average flight time is 3 hours and 30 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, United offers the cheapest flight tickets to Chicago.

Flying from Harlingen Valley International Airport (HRL) to Chicago: what you need to know

  • Expect to be travelling for 3 hours 50 minutes. On average, that's the duration of a direct flight from Harlingen Valley International Airport to Chicago.

  • Chicago and Harlingen (where Harlingen Valley International Airport is located) share the UTC-6 timezone. That means you won't have to change your watch on arrival.

  • To avoid rushing for your HRL to Chicago flight, allow plenty of time to check in and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • Flying during a popular month such as April? Public holidays and other high seasons can mean longer queues at check-in and security. Play things extra safe and get there up to four hours ahead of international flights and two hours before a domestic departure.

  • Start your trip at HRL and travel straight to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for Harlingen Valley International Airport to Chicago tickets.

  • United Airlines is a well-known carrier that operates direct flights from Harlingen Valley International Airport to Chicago.

  • Located around 5 kilometres from central Harlingen, HRL can be reached in about 10 minutes by car, depending on traffic. Travelling on public transport takes roughly 30 minutes.

  • Want a stress-free start to your journey? Stay near HRL. Whether you have an early flight from Harlingen Valley International Airport to Chicago or just don't want to be rushed, these hotels are a convenient choice:

  • Harlingen Valley International Airport gets high marks for on-time performance. 81% of flights that take off from HRL land on time.

  • The address for HRL is 3002 Heritage Way.

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

  • The best price we've seen for a one-way Harlingen Valley International Airport to Chicago flight is $163. The cheapest price for a return flight is $286. Bear in mind fares may change due to demand at the time of booking.

  • To pick up cheap flights from HRL to Chicago, book early. Airlines generally offer the most competitive fares when flights first go on sale.

  • Landing cheap tickets from Harlingen Valley International Airport to Chicago is more likely if you can be flexible with your travel plans. Use the 'Whole month' search tool to access the lowest prices across the month and score an awesome deal.

  • Picking up a cheap flight from HRL to Chicago is a breeze with Price Alerts. All you need to do is set up one of these automatic notifications and we'll let you know as soon as a cheaper option becomes available.

  • Tailor your trip with filters. Choose your ideal departure and arrival times, total journey duration and airlines. You can also sort the results by 'Fastest,' 'Cheapest' or 'Best' flights from Harlingen Valley International Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It'll take you about 30 minutes to get to the centre driving.

  • If you're travelling by public transport, expect a journey time of around 45 minutes.

  • If you have a late flight from Harlingen Valley International Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • To lock in the lowest price, reserve your ride from Chicago O'Hare International Airport around four weeks in advance of your flight from HRL to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Harlingen Valley International Airport to Chicago has landed and you've made your way through the terminal, the drive should be around 25 minutes.

  • If you're catching public transport, it'll take around 30 minutes.

  • You'll find some comfortable places to park your luggage (and yourself) near MDW. Unwind and get cosy after your HRL to Chicago flight at any of these perfectly located options:

  • Lock in the lowest price by booking your ride from MDW four weeks ahead of time. You'll also have access to a wider selection of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Harlingen Valley International Airport to Chicago and head for your hotel or start exploring right away. The centre of Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to reach by car.

  • Public transport will get you there in roughly 2 hours.

  • If you don't want to travel to the centre, find a hotel near RFD. Get settled at one of these options after your HRL to Chicago flight:

  • If you're hoping for a specific model or make, booking early increases your chances of getting what you want. Book your ride from RFD a couple of weeks ahead of your flight from Harlingen Valley International Airport to Chicago.

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

Best time to go to Chicago

  • It's time to work out your trip dates for your flight from Harlingen Valley International Airport to Chicago. July is the most popular month to travel to Chicago. If you want a quieter vibe, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your Harlingen Valley International Airport to Chicago plane ticket then if that's the weather you find most pleasant.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from HRL to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. Start your sightseeing at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.