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Cheap flight tickets 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 Airport 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 RM993. Find the lowest prices on one-way and return tickets right here.
Chicago.RM993 per passenger.Departing Sat, 25 Apr, returning Wed, 29 Apr.Return flight with United.Outbound indirect flight with United, departs from Harlingen on Sat, 25 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in Harlingen.Price includes taxes and charges.From RM993, select.
Chicago.RM1,000 per passenger.Departing Fri, 24 Apr, returning Sat, 2 May.Return flight with United.Outbound indirect flight with United, departs from Harlingen on Fri, 24 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sat, 2 May, arriving in Harlingen.Price includes taxes and charges.From RM1,000, select.
Chicago.RM1,370 per passenger.Departing Wed, 18 Mar, returning Wed, 25 Mar.Return flight with United.Outbound indirect flight with United, departs from Harlingen on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 25 Mar, arriving in Harlingen.Price includes taxes and charges.From RM1,370, select.
Chicago.RM1,372 per passenger.Departing Mon, 30 Mar, returning Mon, 6 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Harlingen on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 6 Apr, arriving in Harlingen.Price includes taxes and charges.From RM1,372, select.
Chicago.RM1,374 per passenger.Departing Fri, 5 Jun, returning Sun, 7 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Harlingen on Fri, 5 Jun, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 7 Jun, arriving in Harlingen.Price includes taxes and charges.From RM1,374, select.
Chicago.RM1,510 per passenger.Departing Fri, 24 Jul, returning Sun, 26 Jul.Return flight with United.Outbound indirect flight with United, departs from Harlingen on Fri, 24 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sun, 26 Jul, arriving in Harlingen.Price includes taxes and charges.From RM1,510, select.
Chicago.RM1,942 per passenger.Departing Fri, 31 Jul, returning Sun, 2 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Harlingen on Fri, 31 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Sun, 2 Aug, arriving in Harlingen.Price includes taxes and charges.From RM1,942, select.
Chicago.RM2,200 per passenger.Departing Wed, 5 Aug, returning Mon, 10 Aug.Return flight with United.Outbound indirect flight with United, departs from Harlingen on Wed, 5 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Harlingen.Price includes taxes and charges.From RM2,200, select.

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 April.
Mar
from RM1,370
Apr
from RM993
May
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Jun
from RM1,374
Jul
from RM1,510
Aug
from RM2,200
Sep
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Oct
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Nov
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Dec
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Jan
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Feb
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Alternative Harlingen to Chicago routes

Looking for the cheapest, fastest or easiest route from Harlingen to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from RM1,025
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from RM993
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Harlingen to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM993
Cheapest month to flyApril

Check out these Chicago hotels

Ready to plan your stay? Other travellers rate these Chicago hotels for cleanliness, service and location.
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The St. Regis Chicago
1.45 km from city centre
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The Sono Chicago
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The Peninsula Chicago
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The St. Regis Chicago
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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 RM993. 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 RM993.
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 RM993.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Harlingen Airport to Chicago on Saturday, 25 April 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.

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

  • Take a direct flight from Valley International Airport to Chicago and you'll be travelling for an average of 3 hours 50 minutes.

  • Chicago's timezone is UTC-5, which is the same as Harlingen (the location of Valley International Airport).

  • For a relaxed start to your HRL to Chicago flight, leave plenty of time for things like check-in and baggage drop. Turning up two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • If you're travelling during a bank holiday or another peak period, allow for even more time. A good general rule is two hours before domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • You can book a direct Valley International Airport to Chicago ticket. Begin your trip at HRL and arrive at O'Hare International Airport (ORD).

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

  • HRL is about 5 kilometres from central Harlingen. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 10 minutes or so to arrive, depending on traffic conditions.

  • If you have an early flight from Valley International Airport to Chicago, why not stay somewhere nice and close? Avoid the stress of rushing to the airport (and enjoy some extra shut-eye) at Pool and Hot Tub Lakefront Harlingen Home. Pool and Game Room Waterfront Harlingen Home is another convenient option near HRL.

  • Valley International Airport maintains a strong on-time record, reducing the likelihood of delays. Departures from HRL arrive on schedule 82.44% of the time.

  • HRL is located at 3002 Heritage Way.

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

  • RM461 is currently the lowest price for a one-way Valley International Airport to Chicago flight. A return flight ticket starts from RM993. These fares can change depending on availability and demand.

  • To snag cheap flights from HRL to Chicago, book your trip one month before your departure date.

  • The best month for scoring cheap Valley International Airport to Chicago tickets is May. Use the 'Whole month' tool to compare flight prices, then choose the dates that offer the biggest savings.

  • Finding a cheap flight from HRL to Chicago couldn't be easier with Price Alerts. All you need to do is create one of these automatic notifications and we'll get in touch when the price has dropped.

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

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're grabbing a cab or a ride-share, the drive takes about 35 minutes.

  • When travelling on public transport, expect a journey time of around 55 minutes.

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Valley International Airport to Chicago. Book one of these accommodation options near ORD instead:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are well-known companies to choose from here.

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

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

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 19 kilometres from central Chicago. Once you've hopped off your flight from Valley International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a cab or ride-share.

  • If you travel by public transport, you'll reach the centre in 45 minutes or so.

  • There are some great places to drop your things at near MDW. Settle in and get cosy after your HRL to Chicago flight at one of these perfectly located options:

  • The fastest way to reach your destination is with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and be on your way in a flash.

  • Get the pick of the lot. Reserving your ride from MDW four weeks in advance often means better deals and a bigger choice of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from central Chicago. It takes about 1 hour 25 minutes to reach the city centre by car once you've hopped off your flight from Valley International Airport to Chicago.

  • Public transport can get you there in roughly 4 hours 15 minutes.

  • Check in to a hotel close to RFD and go from landing to lounging in your room in a flash. Whether you're arriving on a late HRL to Chicago flight or just want to simplify your travel plans, these accommodation options bring comfort closer to you:

  • Start your trip without stressing over how to arrive at your destination with a Chicago Rockford International Airport rental car. Book your wheels with trusted names here like Budget, Alamo and National.

  • Rental agencies sometimes offer promotions for early bookings, so reserve your vehicle from RFD a few weeks in advance of your flight from Valley International Airport to Chicago. Plan ahead and your wallet will thank you.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before locking in your flight from Valley International Airport to Chicago. The city buzzes in high season, but hotel rates are typically higher and attractions can get crowded. Go to Chicago in the off-season if you like a quieter vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Valley International Airport to Chicago flight ticket then if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from HRL to Chicago around that time if you want to travel when it's cooler.

More about Chicago

Explore more of United States

  • You've done Chicago, now it's time to explore other corners of United States. Journey about 451 kilometres south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, your itinerary will be busy.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Harlingen to Chicago

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