$425 Find Cheap Flights from Chicago to São Miguel - Compare and Save

1 adult
1 adult, Economy, 0 bags

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KAYAK's insights & trends for Chicago to São Miguel flights

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

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to São Miguel?

No, with an average price for the route of $498, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to São Miguel?

The cheapest month for flights from Chicago O'Hare Intl Airport to São Miguel is November, when tickets cost $0 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,652 and $1,464 respectively.

Good to know

Low season

April

Cheapest flight

$425
Best time to beat the crowds with an average 51% drop in price.
Most popular time to fly with an average 54% increase in price.
Flight from Chicago to Ponta Delgada

FAQs - booking São Miguel flights

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

    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 São Miguel.

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

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

    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 São Miguel 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 São Miguel?

    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 São Miguel 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 São Miguel

 
Need help choosing which airline to fly with from Chicago to São Miguel? 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 10172 reviews
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

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

2.0 MediocreWilliam, Aug 2026
Read more United Airlines reviews

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.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

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.

Not have my bag forced to be checked when I had a carry on included on my ticket. Staff was very rude to me for asking why they were doing this. I was told there was no more room for carry ons but there was plenty of space in the overhead compartments

The crew was excellent. What I did not enjoy was the food. I have taken many international flights and this was on the low end. Otherwise the trip was fine.

Seats were the most uncomfortable seats i ever experienced on a flight to Europe from Boston. It was a waist of money in buying premium seats for top dollars. I want my money back for what i paid extra for my seats. Awful conditions!

Boarding felt a little chaotic as everyone was waiting around the gate. Food was great, service was good.

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 to São Miguel

Complete your trip to São Miguel with a hotel stay or car rental