Find cheap flights from Chicago to São Miguel - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
Booking Insights

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 $542, 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 July and June, when the average cost of round-trip tickets is $1,464 and $1,251 respectively.

Good to know

Low season

April
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly and prices are also 3% lower on average.

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.
7.3
United AirlinesOverall score based on 10453 reviews
8.1Crew
7.7Boarding
7.1Entertainment
6.7Food
7.3Comfort
Airline reviews

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

6.0 GoodJoann, Oct 2026
Read more United Airlines reviews

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The flight was generally comfortable. However, it was the smallest bathroom on a plane that I have ever seen.

Business class seats were harder than expected, and lie flat we're not very comfortable. Less expensive than other business class flights, and much better than flying economy. The crew was excellent, as was the food.

Boarding was slow and getting off the plane took a long time. The crew did not have enough water for the trip.

Boarding was a bit chaotic, planes were on the oldish side. Otherwise, very nice flight. Would fly them again.

Turkey slices for breakfast. What happened to eggs, bacon, and sausage? The TV shows could’ve been more comprehensive as well as the movies.

The in flight meal was absolutely delicious. One thing I noted was that the meals weren’t just prepackaged tv dinner style options but were actual prepared meals you could tell were cooked that day in a kitchen and individually packaged for the flight.

The flight took off two hours late. What was good was that I was getting an information on this earlier in the day. The lounge agent sent the passengers to the gate way too early. That was annoying. The food aboard was disgusting. The service aboard was okay. The seats were good. Overall, it's a very mediocre experience. Well, it's not a five-star airline and not one that aspires to be one. Comparing TAP Portugal to Iberia or Lufthansa, I'd rather see it as a three-star airline, even though it's website works much better than what Lufthansa has been trying to pull off for the past decade.

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.

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.

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