$308 Find Cheap Flights from Chicago to São Miguel

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 São Miguel departing on 10/22. 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

KAYAK searches hundreds of travel sites at once for deals on flights to São Miguel

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to São Miguel, 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 São Miguel, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to São Miguel

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Ponta Delgada
Ponta Delgada1 stop$527
Ponta Delgada
Ponta Delgada1 stop$527

Book Cheap Chicago to São Miguel 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 São Miguel 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 São Miguel

Fri, Nov 28 - Fri, Dec 5
TAP AIR PORTUGAL Logo
8:15 pm - 11:45 pmORD-PDL
22h 30m1 stop
TAP AIR PORTUGAL Logo
6:30 am - 3:15 pmPDL-ORD
13h 45m1 stop
$527TAP AIR PORTUGAL
Find Deal
Fri, Mar 13 - Sun, Mar 22
TAP AIR PORTUGAL Logo
9:15 pm - 6:35 pmORD-PDL
17h 20m1 stop
TAP AIR PORTUGAL Logo
6:30 am - 3:45 pmPDL-ORD
13h 15m1 stop
$598TAP AIR PORTUGAL
Find Deal
Tue, Oct 7 - Tue, Oct 21
Multiple Airlines Logo
11:13 am - 11:45 pmORD-PDL
31h 32m2 stops
Multiple Airlines Logo
5:30 pm - 12:45 pmPDL-ORD
24h 15m1 stop
$692Multiple Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 29
Multiple Airlines Logo
6:40 am - 6:50 pmORD-PDL
31h 10m2 stops
Multiple Airlines Logo
5:20 pm - 12:45 pmPDL-ORD
23h 25m1 stop
$711Multiple Airlines
Find Deal
Sat, Oct 18 - Wed, Oct 29
Multiple Airlines Logo
6:40 am - 2:35 pmORD-PDL
26h 55m2 stops
Multiple Airlines Logo
5:20 pm - 12:45 pmPDL-ORD
23h 25m1 stop
$745Multiple Airlines
Find Deal
Sun, Oct 5 - Fri, Oct 17
Multiple Airlines Logo
7:25 pm - 9:45 amORD-PDL
33h 20m3 stops
Multiple Airlines Logo
7:50 am - 9:15 pmPDL-ORD
18h 25m2 stops
$754Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
TAP AIR PORTUGAL Logo
7:00 am - 6:35 pmORD-PDL
30h 35m2 stops
TAP AIR PORTUGAL Logo
7:25 pm - 3:00 pmPDL-ORD
24h 35m1 stop
$755TAP AIR PORTUGAL
Find Deal
Fri, Nov 28 - Fri, Dec 5
TAP AIR PORTUGAL Logo
8:15 pm - 6:35 pmORD-PDL
17h 20m1 stop
TAP AIR PORTUGAL Logo
6:30 am - 7:43 pmPDL-ORD
18h 13m2 stops
$761TAP AIR PORTUGAL
Find Deal
Mon, Oct 6 - Tue, Oct 21
Multiple Airlines Logo
11:13 am - 2:45 pmORD-PDL
22h 32m2 stops
Multiple Airlines Logo
5:30 pm - 12:45 pmPDL-ORD
24h 15m1 stop
$763Multiple Airlines
Find Deal
Fri, Nov 28 - Fri, Dec 5
TAP AIR PORTUGAL Logo
8:15 pm - 8:25 amORD-PDL
31h 10m1 stop
TAP AIR PORTUGAL Logo
6:30 am - 7:43 pmPDL-ORD
18h 13m2 stops
$769TAP AIR PORTUGAL
Find Deal
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 to São Miguel?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $376, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to São Miguel?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to São Miguel, 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 São Miguel is October, when tickets cost $850 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $1,498 and $1,185 respectively.

Good to know

Low seasonJanuary
Cheapest flight$308
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport 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.

  • What is the cheapest time of day to fly to São Miguel?

    The cheapest time of day to fly to São Miguel is generally in the evening, when round-trip flights cost $1,084 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to São Miguel is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,487.

Reviews of the top airlines flying from Chicago to São Miguel

 
See real verified KAYAK customer reviews for airlines flying from Chicago to São Miguel. 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 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 8924 reviews
7.7Boarding
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

An old airplane with very uncomfortable seats in the Comfort “class! Small, narrow, and hard seat. Entertainment options are inferior, old movies. Boarding started at the back of the airplane, as we entered the aircraft last instead of after business class, risking the possibility that the comfort section would not have room for carry-on in the overhead bin. The food was ok. White wine was terrible. Overall, the flight felt worse than cheap airliners, and the price was as high as premium carriers.

I will avoid TAP if I can, the ground experience was very poor with bad behaviour from the ground crew and it was only a bit better on the aircraft.

I had a business class ticket from EWR to Madrid with a layover at LIS for 11 hours. It was obvious that I needed to pick up my luggage in Lisbon for 11 hours and check it in again when boarding the second flight to Madrid. Before buying the ticket, I called TAP customer service. Customer service assured me that I could get my luggage in Lisbon. When I arrived at Newark airport, I immediately asked to check my luggage to Lisbon. However, the TAP employee refused me, saying that I should resolve this issue upon arrival in Lisbon. She checked my luggage to Madrid. I asked the TAP employee at the gate to help me when boarding the plane, I asked the flight attendants manager on board the plane to help me. All the employees refused to help me and said that I should resolve this issue in Lisbon. It took me 4 hours to resolve this issue in Lisbon. I arrived at 11am and they didn't give me my luggage until 3pm. As a result, I was so tired after a sleepless night on the plane and 4 hours on my feet at the airport and all my plans were ruined that I couldn't fly to Madrid. It was a terrible experiance,

The seats were not designed to comfortably see people in coach for more than 10 minutes

A good, comfortable flight with friendly crew and good entertainment options.

Very rude person at the boarding desk; flight attendant coughing 3 inches from my face three times- not even covering her mouth; boarding process very unacceptable for older people with stairs to all planes (are you all stuck in the 1960’s?). I am sure that I am not remembering all of the negative things, but I am sure you get the message!

There was chaos at the Naples airport. We arrived three hours early for the flight but there was no invitation available about where to go to check bags until an hour later. Then we had to go to a different terminal to check our bags and check in and back to the first to board.

We flew TAP last October from Newark to Lisbon. The meal was bad. This flight had good food. Also, this flight was delayed. There were TAP employees waiting at Lisbon to make sure we made our connecting flight. I find the TAP website and app frustrating, but the service once we reached the airport was very good

The airport temperature at the airport and on the flight was too warm

Boarding too way too long. Biggest peeve: zero in-seat power in economy! No plug sockets, no USB ports. Plane was an A330, so not old.

Everything you need to know for your flight to São Miguel

Cabin class types available on flights to Chicago

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.