CHI - PDL

$435 Find Cheap Flights from Chicago to Ponta Delgada

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Ponta Delgada departing on 6/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Ponta Delgada

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Ponta Delgada, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Ponta Delgada, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$818
Multiple Airlines
Mon 7/20Mon 7/27
MDW - PDL • 1 stop
Cheapest one-way
$435
Multiple Airlines
Mon 6/8
MDW - PDL • 1 stop
Top airlines
Cheapest • from $886 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Ponta Delgada. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $852 (round-trip)
Shortest trip • 9h 32m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Ponta Delgada!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Ponta Delgada (CHI-PDL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Ponta Delgada that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Ponta Delgada

Mon, Jul 20 - Mon, Jul 27
Multiple Airlines Logo
3:20 pm - 9:05 am
MDW
-
PDL
12h 45m
1 stop
Multiple Airlines Logo
9:35 am - 9:40 am
PDL
-
MDW
29h 05m
1 stop
$818Multiple Airlines
Fri, Aug 21 - Sat, Aug 29
Multiple Airlines Logo
10:25 am - 9:35 am
MDW
-
PDL
18h 10m
1 stop
Multiple Airlines Logo
11:30 am - 9:40 am
PDL
-
MDW
27h 10m
1 stop
$857Multiple Airlines
Fri, Jul 3 - Tue, Jul 14
Multiple Airlines Logo
3:20 pm - 9:35 am
MDW
-
PDL
13h 15m
1 stop
Multiple Airlines Logo
10:30 am - 2:35 pm
PDL
-
MDW
33h 05m
1 stop
$858Multiple Airlines
Fri, Jul 3 - Sat, Jul 11
Multiple Airlines Logo
3:20 pm - 9:35 am
MDW
-
PDL
13h 15m
1 stop
Multiple Airlines Logo
11:30 am - 9:40 am
PDL
-
MDW
27h 10m
1 stop
$878Multiple Airlines
Sun, Aug 16 - Wed, Aug 26
TAP AIR PORTUGAL Logo
6:00 pm - 3:00 pm
ORD
-
PDL
16h 00m
1 stop
TAP AIR PORTUGAL Logo
6:30 am - 2:45 pm
PDL
-
ORD
13h 15m
1 stop
$886TAP AIR PORTUGAL
Mon, Jul 20 - Mon, Jul 27
Multiple Airlines Logo
11:05 am - 9:05 am
ORD
-
PDL
17h 00m
2 stops
Multiple Airlines Logo
9:35 am - 10:16 am
PDL
-
ORD
29h 41m
2 stops
$887Multiple Airlines
Sun, Oct 4 - Sat, Oct 10
TAP AIR PORTUGAL Logo
6:00 pm - 11:45 pm
ORD
-
PDL
24h 45m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
PDL
-
ORD
25h 25m
1 stop
$889TAP AIR PORTUGAL
Sun, Jul 19 - Mon, Jul 27
Multiple Airlines Logo
10:25 am - 8:10 am
MDW
-
PDL
16h 45m
1 stop
Multiple Airlines Logo
9:35 am - 9:40 am
PDL
-
MDW
29h 05m
1 stop
$894Multiple Airlines
Tue, Jun 2 - Mon, Jun 8
Multiple Airlines Logo
7:25 am - 6:40 am
ORD
-
PDL
18h 15m
1 stop
Multiple Airlines Logo
3:50 pm - 7:25 pm
PDL
-
ORD
32h 35m
2 stops
$895Multiple Airlines
Sat, Sep 26 - Sat, Oct 10
TAP AIR PORTUGAL Logo
6:05 pm - 2:35 pm
ORD
-
PDL
15h 30m
1 stop
TAP AIR PORTUGAL Logo
3:50 pm - 4:00 pm
PDL
-
ORD
29h 10m
1 stop
$911TAP AIR PORTUGAL
Booking Insights

KAYAK's insights & trends for Chicago to Ponta Delgada flights

Get data-powered insights and trends into flights from Chicago to Ponta Delgada to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Ponta Delgada?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Ponta Delgada departing in July.

What is the cheapest month to fly from Chicago to Ponta Delgada?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Ponta Delgada, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Ponta Delgada is April, where tickets cost $469 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is $1,030 and $888 respectively.

Good to know

Cheapest flight$435
Most popular time to fly with an average 13% increase in price.
Flight from Chicago Midway Airport to Ponta Delgada

When to book flights from Chicago to Ponta Delgada

Are your dates flexible? Find out the best times to travel from Chicago to Ponta Delgada based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Ponta Delgada

  • What is the cheapest flight from Chicago to Ponta Delgada?

    In the last 3 days, the lowest price for a flight from Chicago to Ponta Delgada was $435 for a one-way ticket and $818 for a round-trip.

  • Do I need a passport to fly between Chicago and Ponta Delgada?

    Yes

  • Which airports will I be using when flying from Chicago to Ponta Delgada?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Ponta Delgada Nordela.

  • Which aircraft models fly most regularly from Chicago to Ponta Delgada?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Ponta Delgada?

    Star Alliance is the only airline alliance operating flights between Chicago and Ponta Delgada.

  • Which is the best airline for flights from Chicago to Ponta Delgada, United Airlines or TAP AIR PORTUGAL?

    The two airlines most popular with KAYAK users for flights from Chicago to Ponta Delgada are United Airlines and TAP AIR PORTUGAL. With an average price for the route of $1,096 and an overall rating of 7.4, United Airlines is the most popular choice. TAP AIR PORTUGAL is also a great choice for the route, with an average price of $936 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Ponta Delgada?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Ponta Delgada.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Ponta Delgada?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Ponta Delgada from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Ponta Delgada?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Ponta Delgada with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Ponta Delgada?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Ponta Delgada from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Ponta Delgada

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Ponta Delgada. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Ponta Delgada? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9678 reviews
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

The chicken was so dry it was impossible to eat. No substitute was offered. The port to charge my phone was broken and all I got was a shrug from the crew. The entertainment system was glitchy and subtitles didn’t load. Crew seemed fully uninterested and unfriendly.

The flight crew were absolute rock stars. When they came to the gate they looked like royalty, so chic. They also were extremely kind. Food was good and I loved the lack of plastic waste. The flight was lovely and smooth.

We were unable to check in due to technical problems on TAP’s end. The flight was delayed forty minutes with no reason given. We received timely notice of the flight delay. We were also notified of a gate change. The new gate was at a different terminal. When we got to the new terminal, we learned that we had to go back to the old terminal first to check in. This information should have been included along with the gate change notification. Also unexplained, the steward skipped us when offering breakfast.

They left our luggage uncovered on tarmac in pouring rain during an hour delay of departure! At our final destination, we found ALL OF OUR CLOTHES/SHOES soaked all the way through!! Our 1st connection plane was a great business class accommodation but only 50 minutes long. Our 2nd connection from Lisbon (another delay with luggage uncovered on tarmac) had only the extra legroom and mediocre food in business class - no entertainment and no extra comfort seating. Will not use TAP Air Portugal again!

The food left a lot to be desired. The crew was great

Horrible experience at tbe check in ladie she was very racist ,she doesn't speak portuguese too and forced me to check in my carrion bag and I saw everyone with carrion bag inside anda lot of space ,she was rude unprofessional

Departed late. Flight crew some of the most professional I have ever experienced. First time we’ve flown this airline

No difference between business class and normal same seat everything same, waste of money

They allowed me to book the flight, which took quite an effort to find the best option for us, and then 2 months later, cancelled it because they didn't think 90 minutes was enough time to get between connections. Why let me book the flight in the first place? I am somewhat disappointed in Kayak and will be choosing other options in the future

Absolutely unacceptable level of service for a Business class: lousy drink and food options, disgusting food (inedible meat, watery rice, etc...), pathetic level of attentiveness from staff, Business class restrooms were not accessible for long periods because blocked of by staff...overall extremely disappointing, will NEVER fly Business on TAP again.

Everything you need to know for your flight from Chicago to Ponta Delgada

Information on your arrival and departure airports