$435 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 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 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$818
Ponta Delgada
Ponta Delgada1 stop$818

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

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
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
Mon, Aug 24 - Mon, Aug 31
Multiple Airlines Logo
1:50 pm - 6:45 am
ORD
-
PDL
11h 55m
1 stop
Multiple Airlines Logo
9:35 am - 11:00 am
PDL
-
ORD
30h 25m
1 stop
$912Multiple Airlines
Fri, Aug 21 - Sun, Aug 30
TAP AIR PORTUGAL Logo
6:00 pm - 6:45 pm
ORD
-
PDL
19h 45m
1 stop
TAP AIR PORTUGAL Logo
6:30 am - 4:00 pm
PDL
-
ORD
14h 30m
1 stop
$925TAP AIR PORTUGAL
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 much is a round-trip flight from Chicago to Azores?

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 Azores departing in July.

What is the cheapest month to fly from Chicago to Azores?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Azores, 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 Azores is April, when tickets cost $469 (return) on average. On the other hand, the most expensive months are November and July, when 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

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 9681 reviews
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
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 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.