$290 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 9/22. 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.

Flights Deals
Booking Insights
Flights 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 Delgada2 stops$692
Ponta Delgada
Ponta Delgada2 stops$692

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

Wed, Sep 17 - Sun, Sep 21
United Airlines Logo
9:31 pm - 8:40 amORD-PDL
30h 09m2 stops
United Airlines Logo
11:00 am - 9:16 pmPDL-ORD
15h 16m2 stops
$692United Airlines
Find Deal
Thu, Sep 18 - Wed, Sep 24
United Airlines Logo
12:50 pm - 8:40 amORD-PDL
14h 50m2 stops
United Airlines Logo
11:00 am - 6:16 pmPDL-ORD
12h 16m2 stops
$720United Airlines
Find Deal
Tue, Nov 25 - Sun, Nov 30
 Logo
7:15 am - 11:35 pmORD-PDL
35h 20m3 stops
 Logo
9:30 am - 4:20 pmPDL-ORD
35h 50m3 stops
Tue, Nov 25 - Sun, Nov 30
 Logo
4:20 pm - 11:35 pmORD-PDL
26h 15m2 stops
 Logo
9:30 am - 4:20 pmPDL-ORD
35h 50m3 stops
Thu, Sep 18 - Wed, Sep 24
United Airlines Logo
3:45 pm - 8:40 amORD-PDL
11h 55m1 stop
United Airlines Logo
11:00 am - 6:16 pmPDL-ORD
12h 16m2 stops
$770United Airlines
Find Deal
Sun, Sep 7 - Sun, Sep 14
TAP AIR PORTUGAL Logo
6:00 pm - 11:45 pmORD-PDL
24h 45m1 stop
TAP AIR PORTUGAL Logo
7:40 pm - 4:40 pmPDL-ORD
26h 00m1 stop
$777TAP AIR PORTUGAL
Find Deal
Wed, Sep 17 - Sun, Sep 21
 Logo
5:05 am - 6:50 pmORD-PDL
32h 45m3 stops
 Logo
5:30 pm - 5:39 pmPDL-ORD
29h 09m2 stops
Thu, Sep 18 - Wed, Sep 24
TAP AIR PORTUGAL Logo
6:00 pm - 1:35 pmORD-PDL
14h 35m1 stop
TAP AIR PORTUGAL Logo
7:30 pm - 12:35 pmPDL-ORD
22h 05m1 stop
$807TAP AIR PORTUGAL
Find Deal
Mon, Sep 8 - Mon, Sep 15
TAP AIR PORTUGAL Logo
6:10 pm - 6:35 pmORD-PDL
19h 25m1 stop
TAP AIR PORTUGAL Logo
6:30 am - 4:40 pmPDL-ORD
15h 10m1 stop
$850TAP AIR PORTUGAL
Find Deal
Mon, Aug 18 - Wed, Aug 27
TAP AIR PORTUGAL Logo
4:27 pm - 9:45 amORD-PDL
36h 18m2 stops
TAP AIR PORTUGAL Logo
3:45 pm - 12:50 pmPDL-ORD
26h 05m1 stop
$865TAP 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 $939, 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 February, when tickets cost $804 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $1,526 and $1,185 respectively.


Good to know

Low seasonJanuary
Cheapest flight$290
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 5% lower on average.
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 8904 reviews
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

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.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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.

boarding is so disorganized, i was literally appalled at the boarding experience

Comfortable but not Polaris or Delta comfort Business Class. Overall 7 out of 10

Tap air Portugal was the best I will traveling again with u guys. Thank u.

The long wait at JFK made the trip horrible. Also not having enough buses when we deplaned was annoying

Terrible! I had to cancel our flights due to my wife Carmen requiring an unexpected second cancer surgery. I first contacted orbitz about obtaining a credit due to medical interruption and orbitz directed me to TAP. I contacted TAP and the representative directed me back to orbitz and refused to even explain what TAP’s medical interruption policy was or how it worked—I wanted that information for a second call to orbitz. Terrible service at a particularly difficult time.

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.