$429 Find Cheap Flights from Chicago to Azores - Compare and Save

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1 adult, Economy, 0 bags

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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.

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

The cheapest month for flights from Chicago to Azores is November, when tickets cost $0 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $1,464 and $1,251 respectively.

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Cheapest flight

$429
Flight from Chicago 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

 
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 10210 reviews
6.7Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

10.0 ExcellentSharon, Sep 2026
Read more United Airlines reviews

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

The plane was FABULOUS. The crew were wonderful and the food more than I expected.

The food was dry and tasteless. Boarding process was ridiculous. Lounge is Lisbon was of very poor quality. The website is nearly unusable. Customer service was challenging. This was my first transatlantic business class flight with TAP. There will not be another.

Disappointing Compared to other airlines , this one was the most expensive. But not even close, in getting what you paid for.

TAP canceled connection and we had to wait 15 hours for another flight to Milan. There were plenty of. Seats on earlier but because we were Excellence Class the would not let us downgrade which we were willing to. Don’t understand their logic? Plenty of seats but we couldn’t / they wouldn’t make the change.

Excellent experience - from boarding through the super smooth flight The food was mediocre and the app could be better but overall great experience

No onboard entertainment or food, but that was okay because it was a short flight. Pretty much everyone just slept on the plane. The plane was comfortable enough.

This was one of the worst flights I have ever taken in my entire life. First of all, I traveled Economy, but the seats were TINY and cramped. Not just for me; everyone around me was complaining of the same thing and said they could not get comfortable. Then there was the issue of the heat. For whatever reason the heat on the plane must have been turned to FULL BLAST, because even at 30,000 feet, it was SWEALTERING. Everyone was drench in sweat. Then, they were SO STINGY with the amount of drink they would give you. If you asked for water, it was in a tiny, paper cup (think bathroom cup) and they only filled it 3/4s of the way as if the cost came right out of the pockets of the air stewards. Everything was a money grab, you could tell! You had to pay for the WiFi, which was garbage slow, and the onboard entertainment was limited and stale. If I EVER fly TAP again, it will not be Economy class. What a disaster!

They blocked me from checking in online and they charged me lots of money

Everything was good with Tap Air Portugal. It was Logan Airport that was a problem. The fuel system was down and delayed my 10:40 boarding. I wasn't able to board my flight until 2:00 am...after that my flights were great.

Great staff who were ready working with smile 6 in the morning on New Year’s Day. Although security checkpoint was way too busy, the airline staff were understanding and waited few minutes after boarding. We took off not only exactly on time, but arrived 20 minutes early. Two thumbs up!!!

More options for your flight from Chicago to Azores

Complete your trip to Azores with a hotel stay or car rental