$359 Find Cheap Flights from Chicago to Azores

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 Azores departing on 2/15. 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 Azores

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Azores, 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 Azores, as well as popular online travel agencies
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Cheap Flights from Chicago to Azores

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Ponta Delgada
Ponta Delgada1 stop$545
Ponta Delgada
Ponta Delgada1 stop$545

Book Cheap Chicago to Azores Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Azores 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 Azores

Wed, Mar 4 - Thu, Mar 12
TAP AIR PORTUGAL Logo
7:10 pm - 11:45 pm
ORD
-
PDL
23h 35m
1 stop
TAP AIR PORTUGAL Logo
7:25 pm - 4:25 pm
PDL
-
ORD
25h 00m
1 stop
$545TAP AIR PORTUGAL
Wed, Mar 4 - Thu, Mar 12
TAP AIR PORTUGAL Logo
7:10 pm - 11:45 pm
ORD
-
PDL
23h 35m
1 stop
TAP AIR PORTUGAL Logo
9:35 am - 4:25 pm
PDL
-
ORD
34h 50m
1 stop
$547TAP AIR PORTUGAL
Wed, Mar 4 - Thu, Mar 12
TAP AIR PORTUGAL Logo
7:10 pm - 11:45 pm
ORD
-
PDL
23h 35m
1 stop
TAP AIR PORTUGAL Logo
7:25 pm - 4:25 pm
PDL
-
ORD
25h 00m
1 stop
$576TAP AIR PORTUGAL
Wed, Mar 4 - Thu, Mar 12
TAP AIR PORTUGAL Logo
7:10 pm - 6:35 pm
ORD
-
PDL
18h 25m
1 stop
TAP AIR PORTUGAL Logo
9:35 am - 4:25 pm
PDL
-
ORD
34h 50m
1 stop
$584TAP AIR PORTUGAL
Wed, Mar 4 - Thu, Mar 12
TAP AIR PORTUGAL Logo
7:00 am - 11:45 pm
ORD
-
PDL
35h 45m
2 stops
TAP AIR PORTUGAL Logo
7:25 pm - 4:25 pm
PDL
-
ORD
25h 00m
1 stop
$687TAP AIR PORTUGAL
Fri, Feb 27 - Wed, Mar 4
TAP AIR PORTUGAL Logo
8:15 pm - 8:25 am
ORD
-
PDL
31h 10m
1 stop
TAP AIR PORTUGAL Logo
6:35 am - 3:00 pm
PDL
-
ORD
13h 25m
1 stop
$699TAP AIR PORTUGAL
Tue, Feb 24 - Tue, Mar 3
TAP AIR PORTUGAL Logo
7:00 am - 6:35 pm
ORD
-
PDL
30h 35m
2 stops
TAP AIR PORTUGAL Logo
7:25 pm - 3:00 pm
PDL
-
ORD
24h 35m
1 stop
$702TAP AIR PORTUGAL
Wed, Feb 25 - Mon, Mar 2
Multiple Airlines Logo
10:00 am - 6:20 am
ORD
-
PDL
15h 20m
1 stop
Multiple Airlines Logo
8:05 pm - 9:10 am
PDL
-
ORD
42h 05m
2 stops
$711Multiple Airlines
Fri, Feb 27 - Tue, Mar 3
TAP AIR PORTUGAL Logo
8:15 pm - 11:45 pm
ORD
-
PDL
22h 30m
1 stop
TAP AIR PORTUGAL Logo
7:25 pm - 3:00 pm
PDL
-
ORD
24h 35m
1 stop
$714TAP AIR PORTUGAL
Mon, Mar 23 - Mon, Mar 30
Azores Airlines Logo
1:55 pm - 6:15 am
ORD
-
TER
12h 20m
1 stop
Azores Airlines Logo
4:55 pm - 9:10 am
TER
-
ORD
21h 15m
1 stop
$1,504Azores Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Azores flights

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

How long does a flight from Chicago to Azores take?

The duration of a flight to Azores depends on your arrival airport. The shortest routes to Azores from Chicago are to Ponta Delgada, which takes 14h 20m, Lajes, which takes 19h 30m, and Horta, which takes 26h 25m.

Good to know

Cheapest flight$359
Most popular time to fly with an average 15% increase in price.
Flight from Chicago O'Hare Airport to Ponta Delgada

FAQs - booking Azores flights

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

    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 Azores.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Azores 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 Azores?

    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 from Chicago to Azores with an airline and back with another airline.

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

    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 from Chicago to Azores 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 Azores

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Azores. 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 Azores? 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 9219 reviews
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

Delayed departure Madrid to Lisboa and my luggage no arrived

this flight was awful from pre-boarding to on the plane. There needs to be more coordination between TAP and My Way. We were in first class and I am handicapped. BY the time we got on the plane there was no place for our baggage and the crew did not handle the situation well. They gave us an argument and said that we'd have to have it checked. Then, after I complained they moved some people's bags to put our small carry ons several seats back of our seats which were in Row 4.

Late. Lack of updates. Rude hostesses. Terrible food. Lack of headphones.

Flight was delayed but crew gave little to no communication, then “began boarding” but really just had everyone stand up and wait for an hour without any news or updates, as if we were going to start boarding at any second. Total chaos. Seemed like this was their first time boarding a plane. When we arrived at our destination, we waited for over an hour for the baggage claim belt to even turn on. Probably waited at baggage claim for our luggage for close to two hours. Everyone was very confused and of course we all worried that the luggage was lost. Again, zero communication and everyone we asked just said “I don’t know.” So we were left wondering whether to wait, or file a missing baggage claim, or check the other baggage claim belts (which we did every fifteen-twenty minutes because we were just confused). Lack of communication throughout the experience was a huge issue.

The value is there, but the layovers in Lisbon were not great. The passport control was so bad that a 2 hour layover became very tight and on the return the Terminal was barebones which made it a long 3 hours.

From Casablanca to Lisbon our baggage 2 pound over they want me to pay $120 for 2 pound which unexpected we are two family 8 of us they counters lady her customer service is not good I fly frequently for my business next time fly with TAP Air I will think twice

Booked business with TAP from LAX to Cabo Verde - overall ok, but just doesn’t feel like business class. More of a budget airline

Poor. Our flight was delayed and they told me I would be fine to make my connection in Lisbon, I missed it. Then they told me my bag would be automatically loaded onto my new flight to rome. It wasn’t. It’s been 4 days and I still don’t have it.

I like the price. I dislike the website where I wanted to ask questions about the unusual high prices of the luggage fees. I called the toll free number from the United States and I cannot get through. You should test your own toll free website for info and you will know what I am writing about.

Wonderful just hope the had more direct flights to Boston

Everything you need to know for your flight from Chicago to Azores

Cabin class types available on flights to Azores

Cabin classes available on flights to Azores. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.