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Cheap Flights from Chicago (CHIA) to Ponta Delgada (PDL)

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Flight deals from Chicago to Ponta Delgada

Looking for a cheap last-minute deal or the best return flight from Chicago to Ponta Delgada Airport? If you want to travel next month, return fares start from $1,153. Find the lowest prices on one-way and return tickets right here.
Ponta Delgada.$978 per passenger.Departing Wed, 9 Sep, returning Wed, 16 Sep.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 9 Sep, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Wed, 16 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $978, select.
Ponta Delgada.$978 per passenger.Departing Wed, 11 Nov, returning Sun, 22 Nov.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 11 Nov, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Sun, 22 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $978, select.
Ponta Delgada.$979 per passenger.Departing Wed, 14 Oct, returning Wed, 21 Oct.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 14 Oct, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Wed, 21 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $979, select.
Ponta Delgada.$979 per passenger.Departing Thu, 24 Sep, returning Thu, 1 Oct.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Thu, 1 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $979, select.
Ponta Delgada.$1,153 per passenger.Departing Mon, 10 Aug, returning Wed, 19 Aug.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Ponta Delgada.Inbound indirect flight with United, departs from Ponta Delgada on Wed, 19 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,153, select.
Ponta Delgada.$1,243 per passenger.Departing Wed, 29 Jul, returning Wed, 5 Aug.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 29 Jul, arriving in Ponta Delgada.Inbound indirect flight with United, departs from Ponta Delgada on Wed, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,243, select.
Ponta Delgada.$1,244 per passenger.Departing Wed, 26 Aug, returning Wed, 2 Sep.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 26 Aug, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Wed, 2 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,244, select.
Ponta Delgada.$1,251 per passenger.Departing Wed, 22 Jul, returning Wed, 29 Jul.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 22 Jul, arriving in Ponta Delgada.Inbound indirect flight with United, departs from Ponta Delgada on Wed, 29 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,251, select.
Ponta Delgada.$1,444 per passenger.Departing Fri, 25 Dec, returning Fri, 1 Jan.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Fri, 25 Dec, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Fri, 1 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,444, select.
Ponta Delgada.$1,464 per passenger.Departing Fri, 4 Jun, returning Fri, 11 Jun.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Fri, 4 Jun, arriving in Ponta Delgada.Inbound indirect flight with TAP Air Portugal, departs from Ponta Delgada on Fri, 11 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,464, select.

Find the cheapest month to fly from Chicago to Ponta Delgada

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Ponta Delgada flights are currently cheapest in September.
Jul
from $1,251
Aug
from $1,153
Sep
from $978
Oct
from $979
Nov
from $978
Dec
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Jan
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Feb
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Mar
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Apr
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May
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Jun
from $1,464

Chicago to Ponta Delgada: Alternative routes

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

Ponta Delgada

1km from central Ponta Delgada
ClosestCheapest
from $978
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Chicago to Ponta Delgada: Flight information

The things to know before you go.
Cheapest flight found$978
Cheapest month to flySeptember

Finding cheap flights from Chicago to Ponta Delgada: Frequently asked questions

The best price we found for a return flight from Chicago to Ponta Delgada is $978. 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 Chicago to Ponta Delgada. But we found flights with one stop from $978.
As of July 2026, there are no flights flying from Chicago to Ponta Delgada.
The cheapest month to fly from Chicago to Ponta Delgada is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Ponta Delgada Airport on Wednesday, 9 September 2026.
No airlines currently offer direct flights between Chicago and Ponta Delgada Airport. 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 Ponta Delgada 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 Ponta Delgada is around 40 days in advance, so don’t leave your flight to the last minute.

The cheapest airline that flies to Ponta Delgada is TAP Air Portugal .

Flying from Chicago to Ponta Delgada Joao Paulo II Airport (PDL): What you need to know

  • The timezone in Ponta Delgada is UTC-1, which is five hours ahead of Chicago. Ponta Delgada Joao Paulo II Airport is located in Ponta Delgada.

  • Leave plenty of time to make your flight from Chicago to PDL. A good rule of thumb is to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • With more people on the move during peak months like July, get to the terminal earlier than usual. Two hours for domestic flights and as much as four for international journeys will help you deal with any delays. Remember things also get busy during major holidays like Christmas.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Consider adding a stopover to find cheap flights from Chicago to PDL. Simply deselect 'Direct flights only' when browsing departures from Chicago O'Hare International Airport (ORD). Break the trip up (and maybe score a better deal) by stopping at one of these airports:

    • New York John F. Kennedy International Airport (JFK)

    • Newark Liberty International Airport (EWR)

    • Boston Logan International Airport (BOS)

  • Located around 27 kilometres from central Chicago, ORD can be reached in about 30 minutes by car (depending on traffic). The journey by public transport will take roughly 45 minutes.

  • Looking for a comfortable hotel close to Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Ponta Delgada Joao Paulo II Airport, these accommodation options will have you sleeping just around the corner from the terminal:

  • Of the departures from Chicago O'Hare International Airport, 70% arrive as scheduled at their destination.

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

Chicago Midway International Airport (MDW)

  • Maximise your holiday with a stopover on your flight from Chicago to Ponta Delgada Joao Paulo II Airport. Boston Logan International Airport (BOS) is one of the options between Chicago Midway International Airport and PDL.

  • MDW is around 16 kilometres from central Chicago. It takes 25 minutes or so to get to the airport in a car from the city centre. Public transport takes approximately 30 minutes.

  • Kick off your holiday early with an extra night away from home. Before your Chicago to PDL flight, unwind in one of these hotels close to Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 76%. This figure provides insight into how frequently flights that leave from this airport make it to their destination on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The trip to RFD from central Chicago is around 2 hours on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.

  • Skip the morning rush on departure day — stay close to Chicago Rockford International Airport and know you'll make it to the terminal with time to spare. Get comfy at one of these hotels the day before if you've booked an early Chicago to Ponta Delgada Joao Paulo II Airport flight:

  • Flights departing from RFD reach their destination within the expected time frame 71% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Ponta Delgada Joao Paulo II Airport (PDL)

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Chicago to Ponta Delgada Joao Paulo II Airport. Get comfy at one of these accommodation options near PDL instead:

  • Lock in the lowest price by reserving your vehicle around one week ahead of your Chicago to Ponta Delgada Joao Paulo II Airport flight.

Getting from Ponta Delgada Joao Paulo II Airport (PDL) to central Ponta Delgada

  • Ponta Delgada Joao Paulo II Airport is around 3 kilometres from the centre of Ponta Delgada. It takes around 10 minutes or so to get to the city by car.

  • Travelling on public transport typically takes 20 minutes.

How to find the cheapest flights from Chicago to Ponta Delgada Joao Paulo II Airport (PDL)

  • $534 is the lowest price for a one-way ticket from Chicago to Ponta Delgada Joao Paulo II Airport. Return flights start at $978. These fares can change based on availability and demand.

  • To pick up cheap flights from Chicago to PDL, book ahead. Airlines usually offer their most competitively priced fares when flights first go on sale.

  • The 'Whole month' search tool will show you the cheapest Chicago to Ponta Delgada Joao Paulo II Airport tickets across every month. It's a great way to snap up a bargain if your plans are flexible.

  • Stay on top of deals for plane tickets from Chicago to PDL by setting up a Price Alert. We'll send you an email or notification through the app when a new discounted fare appears.

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

The best time to fly from Chicago to Ponta Delgada Joao Paulo II Airport (PDL)

  • It's time to work out when to book your flight from Chicago to Ponta Delgada Joao Paulo II Airport (PDL). August is when most people travel to Ponta Delgada. If you like your getaways a little more chill, think about going in February.

  • The warmest month in Ponta Delgada is August, with temperatures ranging between 20ºC (68ºF) and 25ºC (77ºF). Lock in your Chicago to PDL plane ticket then if you enjoy this type of weather.

  • If you want cooler conditions, search for a cheap ticket from Chicago to Ponta Delgada Joao Paulo II Airport in February when temperatures are between 12ºC (54ºF) and 17ºC (63ºF).

More about Ponta Delgada

  • When it comes to searching for somewhere to lay your head, you'll find the best stays in Ponta Delgada right here. Browse these options as soon as you've booked your flight from Chicago to Ponta Delgada Joao Paulo II Airport:

  • Every great holiday has to include some sightseeing. Portas da Cidade, Gruta do Carvao and Igreja do Colegio are essential stops on your Ponta Delgada itinerary.

Explore more of Portugal

  • You've seen Ponta Delgada, now it's time to explore more of Portugal. Journey about 161 kilometres northwest to Angra do Heroísmo to check off its must-visit sights. From Monte Brasil Caldeira to Historical Institute of Terceira and Se Cathedral, you'll have a full itinerary ahead.

  • Horta is another must-experience destination in Portugal and is around 274 kilometres west of Ponta Delgada. No journey is complete without visiting Cabeço do Fogo, Vista do Neptuno and Miradouro Mirante.

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