C$160 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

Book the best Chicago fare with no extra fees

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 May.

Harlingen to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$160
Cheapest month to flyMay

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 C$346. 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.
Currently, there are no airlines that fly direct from Harlingen to Chicago. But we found flights with one or more stops from C$346.
As of March 2026, there are no flights flying from Harlingen to Chicago.
The cheapest month to fly from Harlingen to Chicago is usually April.
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 C$346.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Harlingen Airport to Chicago on Saturday, April 25, 2026.
No airlines currently offer direct flights between Harlingen Airport and Chicago. Most routes have one or more stops.
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 March, the average temperature is usually around 3°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 Valley International Airport (HRL) to Chicago: what you need to know

  • Chicago and Harlingen (where Valley International Airport is located) share the UTC-5 timezone. That means you won't need to change your watch when you land.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your flight from HRL to Chicago.

  • Peak months like October or high seasons such as Christmas and New Year will mean longer queues at check-in and security. Play it safe and head to the terminal even earlier. Arriving two hours before a domestic flight and up four hours ahead of an international flight is a wise idea.

  • You won't need your passport or a visa to fly within United States. You will need a valid proof of identity however, like an ID card or driver's licence. Add them to your packing checklist after booking your flight tickets from Valley International Airport to Chicago.

  • To get to HRL from central Harlingen, it'll take about 12 minutes if you're planning to drive. This depends on traffic though. It's approximately 8 kilometres from the airport to the city centre.

  • Need a convenient place to stay before your flight from Valley International Airport to Chicago? Lakefront Harlingen Home With Pool, Yard and Pool Table and Waterfront Harlingen Home w/ Pool, Patio & Gazebo! are near HRL. They're a particularly great option if you have an early flight out.

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

  • The lowest price we've found for a one-way ticket from Valley International Airport to Chicago is C$160. The cheapest price for a return flight is C$346. Bear in mind fares can change due to demand at the time of booking.

  • To find cheap tickets from HRL to Chicago, book ahead. Airlines generally offer the most competitive fares when flights are first made available.

  • The 'Whole month' tool shows you the cheapest tickets from Valley International Airport to Chicago across the month. It's a great way to find a bargain if your trip dates aren't set in stone.

  • Log into your online account or use the app to set up a Price Alert. You'll get notified straight away if there's a cheaper deal on this route. It's simple to do, and it'll save you the hassle of looking for cheap tickets from HRL to Chicago every day.

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

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the most popular month to hop on a flight from Valley International Airport to Chicago while February is the quietest. To work out the best time to go to Chicago, consider the pace you prefer to travel at.

  • Lock in your flight from Valley International Airport to Chicago for July to experience the city during its warmest month. You can expect temperatures to range from 15ºC to 29ºC.

  • Look for cheap flights from HRL to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the top stays in Chicago right here. Check out these hotels after locking in your flight from Valley International Airport to Chicago:

  • There are so many things to do and see in this city it can be difficult to know where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are popular attractions which should feature on any well-planned Chicago itinerary.

Complete your Chicago trip with a car rental

  • Choose one of our car rentals in Chicago and explore the city on your own terms. Easily compare companies in one place to find the perfect set of wheels once you've locked in your hotel and cheap flights from Valley International Airport to Chicago.

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