$415 Find Cheap Flights from Chicago to São Miguel - Compare and Save

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 10/18. 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 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 21% 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

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

Sun, Nov 1 - Sat, Nov 7
TAP AIR PORTUGAL Logo
8:10 pm - 6:35 pm
ORD
-
PDL
17h 25m
1 stop
TAP AIR PORTUGAL Logo
7:25 pm - 3:30 pm
PDL
-
ORD
25h 05m
1 stop
$784TAP AIR PORTUGAL
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
7:25 am - 11:45 pm
ORD
-
PDL
35h 20m
3 stops
Multiple Airlines Logo
6:30 am - 11:00 am
PDL
-
ORD
33h 30m
3 stops
$820Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
TAP AIR PORTUGAL Logo
6:00 pm - 11:45 pm
ORD
-
PDL
24h 45m
1 stop
TAP AIR PORTUGAL Logo
3:30 pm - 12:40 pm
PDL
-
ORD
26h 10m
1 stop
$844TAP AIR PORTUGAL
Fri, Aug 7 - Fri, Aug 28
TAP AIR PORTUGAL Logo
6:00 pm - 3:00 pm
ORD
-
PDL
16h 00m
1 stop
TAP AIR PORTUGAL Logo
6:30 am - 4:00 pm
PDL
-
ORD
14h 30m
1 stop
$845TAP AIR PORTUGAL
Fri, Aug 7 - Fri, Aug 28
TAP AIR PORTUGAL Logo
6:00 pm - 3:00 pm
ORD
-
PDL
16h 00m
1 stop
TAP AIR PORTUGAL Logo
7:40 pm - 4:05 pm
PDL
-
ORD
25h 25m
1 stop
$863TAP AIR PORTUGAL
Fri, Aug 7 - Fri, Aug 28
TAP AIR PORTUGAL Logo
6:00 pm - 3:00 pm
ORD
-
PDL
16h 00m
1 stop
TAP AIR PORTUGAL Logo
7:40 pm - 4:05 pm
PDL
-
ORD
25h 25m
1 stop
$865TAP AIR PORTUGAL
Sat, Aug 29 - Sat, Sep 5
TAP AIR PORTUGAL Logo
6:05 pm - 2:35 pm
ORD
-
PDL
15h 30m
1 stop
TAP AIR PORTUGAL Logo
3:50 pm - 4:00 pm
PDL
-
ORD
29h 10m
1 stop
$866TAP AIR PORTUGAL
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
3:40 pm - 11:45 pm
ORD
-
PDL
27h 05m
2 stops
Multiple Airlines Logo
6:30 am - 11:00 am
PDL
-
ORD
33h 30m
3 stops
$870Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
11:05 am - 6:50 pm
ORD
-
PDL
26h 45m
2 stops
Multiple Airlines Logo
6:30 am - 10:17 am
PDL
-
ORD
32h 47m
2 stops
$871Multiple Airlines
Fri, Aug 7 - Fri, Aug 28
TAP AIR PORTUGAL Logo
6:00 pm - 11:45 pm
ORD
-
PDL
24h 45m
1 stop
TAP AIR PORTUGAL Logo
6:30 am - 4:00 pm
PDL
-
ORD
14h 30m
1 stop
$876TAP AIR PORTUGAL
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 $468, 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 January, 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 $1,098 and $1,025 respectively.

Good to know

Cheapest flight$415
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.

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 9842 reviews
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

2.0 MediocreAnonymous, Jun 2026
ORD - BHM
Read more United Airlines reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

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.

It was a game of hurry up and wait. As advised we arrived at the terminal e hours prior to boarding. We waited about 45 minutes before anyone showed up at the check-in terminal. When someone does arrive she rearranges the line and we think we are going to be checked in. Nope. She leaves and we wait another 15 min. before anyone else shows up. One person got behind her computer and about 15 min later started to check the first person in . Then one more person arrives spends 10-15 behind the desk and then she starts checking in someone. Two more staff arrive and another 10 min or so they are ready to begin checking in people. We have a 11:50 international flight and it is 9:45. And then on of the agents, closes her desk and leaves. And every leg of our flight was delayed; we waited at terminals, we waited to take off, we waited to deplane. After arriving in Porto within 10min of our connection schwduled to take off, we were told to go to the last bus. We waited on the bus (until all the other busses had left) and then we waited another 10 min or so for one of the ground controllers who wanted a ride with us but was busy with a woman who needed the handicap van. He did not help her to the van, but was standing with her and talking with hher. We were rushed through border control and told not to wait for the rest of our party only to get on the plane and then have to wait another 45 min before we were cleared for take off. The waits were not 10 or 20 minutes, they were 35-55 minute waits each time. Miraculously, we made it back only 2 1/2 hours later than we we were originally scheduled. Given the nonchalance and seaming disinterest from many of the staff, I was expecting that we would not get on until much later than that.

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!

On the seat map for this flight with TAP was shown a business class configuration of 2 rows/8 seats. To my surprise, 4 rows/24 seats being the middle is kept empty, old European type. I chose seat 2F, the the leg room economy dimension. This is not what I paid for. Disappointed!

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

The passport control process in Lisbon ranks as a 1 on a 1 to 5 scale. Terrible. In line 2 hours and still missed our first flight. Next day, 1.5 hours but we made the flight. The Business Class food was poor. Unidentifiable. Not tasty at all. Unacceptable in BC. Attendants were adequate. Flight left late and arrived late. After this trip, we will not be flying TAP nor will we be connecting through Lisbon.

Flight attendants in business class were rather indifferent While in second leg operated by Portugalia TAP subsidiary were outstanfy

Great service overall. One of the best international flight experiences Ive had.

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.

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.