HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
São Miguel

$304+ Cheap flights from Chicago (CHI) to São Miguel

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to São Miguel with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Chicago to São Miguel

Cheapest flights from Chicago to São Miguel
Explore the most affordable flight options available from Chicago to São Miguel. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

This oojo deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:15 pmORD - PDL
1 stop17h 20mTAP AIR PORTUGAL
Fri 12/56:30 amPDL - ORD
1 stop13h 55mTAP AIR PORTUGAL
Deal found 11/3$546
This Mytrip deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/22:00 pmORD - PDL
3 stops24h 10mMultiple Airlines
Tue 12/98:00 pmPDL - ORD
2 stops22h 10mMultiple Airlines
Deal found 11/2$657
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:10 pmORD - PDL
1 stop18h 25mTAP AIR PORTUGAL
Wed 12/36:35 amPDL - ORD
1 stop13h 25mTAP AIR PORTUGAL
Deal found 11/2$696
This oojo deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:00 amORD - PDL
2 stops35h 45mTAP AIR PORTUGAL
Tue 12/97:25 pmPDL - ORD
1 stop24h 35mTAP AIR PORTUGAL
Deal found 11/2$704
This oojo deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:25 amORD - PDL
2 stops26h 05mTAP AIR PORTUGAL
Wed 12/176:35 amPDL - ORD
1 stop13h 25mTAP AIR PORTUGAL
Deal found 11/4$723
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:10 pmORD - PDL
1 stop18h 25mTAP AIR PORTUGAL
Fri 11/76:30 amPDL - ORD
1 stop13h 55mTAP AIR PORTUGAL
Deal found 11/1$725
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/289:41 amMDW - PDL
2 stops16h 09mMultiple Airlines
Fri 12/54:50 pmPDL - MDW
2 stops25h 20mMultiple Airlines
Deal found 11/3$928
This Mytrip deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:59 pmMDW - PDL
3 stops31h 51mMultiple Airlines
Fri 1/25:50 pmPDL - MDW
2 stops26h 30mMultiple Airlines
Deal found 11/1$1,858
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:20 amMDW - PDL
2 stops16h 30mMultiple Airlines
Sun 11/94:50 pmPDL - MDW
2 stops25h 17mMultiple Airlines
Deal found 11/3$1,897

Cheap flight deals from Chicago to São Miguel

Keep the following information in mind while searching for Chicago to São Miguel flight deals. Data was last updated November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$546
(oojo)

One-way from

$304
(Mytrip)

Popular in

May

Cheapest in

January

Average price

$885
Provider with most accurate pricing for Chicago (CHI)-Ponta Delgada Nordela flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Ponta Delgada Nordela flights.
Search Deals
From Chicago (CHI) to São Miguel
Search Deals
One-way flight from Chicago (CHI) to São Miguel
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($195 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to São Miguel that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 4, 2025.
Use the filters below to find and compare flights from Chicago to São Miguel that are best for you.

Fly from

Chicago

Fly to

São Miguel

Route

Depart

Return

Price

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 4/3

6:00 pm-6:45 pm

1 stop19h 45m

Ponta Delgada Nordela

Fri 4/10

6:30 am-4:00 pm

1 stop14h 30m

$576

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 4/4

6:15 pm-2:35 pm

1 stop15h 20m

Ponta Delgada Nordela

Sat 4/11

6:30 am-4:15 pm

1 stop14h 45m

$596

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 5/2

6:15 pm-11:45 pm

1 stop24h 30m

Ponta Delgada Nordela

Sat 5/9

7:35 pm-4:00 pm

1 stop25h 25m

$641

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Tue 12/2

8:00 am-11:45 pm

2 stops34h 45m

Ponta Delgada Nordela

Tue 12/9

6:30 am-5:48 pm

2 stops16h 18m

$703

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Tue 12/2

7:00 am-11:45 pm

2 stops35h 45m

Ponta Delgada Nordela

Tue 12/9

7:25 pm-3:00 pm

1 stop24h 35m

$704

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Thu 3/5

7:00 am-6:30 pm

2 stops30h 30m

Ponta Delgada Nordela

Tue 3/17

7:25 pm-4:00 pm

1 stop24h 35m

$723

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Thu 12/11

11:25 am-6:30 pm

2 stops26h 05m

Ponta Delgada Nordela

Wed 12/17

6:35 am-3:00 pm

1 stop13h 25m

$723

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Thu 3/12

12:10 pm-6:30 pm

2 stops26h 20m

Ponta Delgada Nordela

Sat 3/21

7:25 pm-3:45 pm

1 stop24h 20m

$742

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Thu 2/26

9:50 am-6:50 am

2 stops16h 00m

Ponta Delgada Nordela

Mon 3/2

5:40 pm-10:05 am

2 stops21h 25m

$901

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Fri 11/28

9:41 am-6:50 am

2 stops16h 09m

Ponta Delgada Nordela

Fri 12/5

4:50 pm-1:10 pm

2 stops25h 20m

$928

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chicago to São Miguel

Have a flexible travel schedule? Discover the best time to fly to São Miguel from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to São Miguel

What is the cheapest time of day to fly from CHI to LXG?

Find hourly flight availability from Chicago to São Miguel. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

When flying from Chicago to São Miguel, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 34% versus a flight at noon.

Reviews of airlines servicing São Miguel

Get insights into the airlines that provide service to São Miguel. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to São Miguel. Reviews last updated November 4, 2025.
Get a feel of what it's like to fly with United Airlines and TAP AIR PORTUGAL from Chicago to São Miguel by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,999 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
TAP AIR PORTUGAL
7.1
Good
2,046 reviews
United Airlines
7.4
Good
8,999 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Chicago to São Miguel. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to São Miguel?

    Airlines like TAP AIR PORTUGAL fly from Chicago to São Miguel in about 19h 45m. The time it takes to get you to your destination can typically vary by up to . There are 3237 mi between Chicago and São Miguel.

  • Can I find deals for flights from Chicago to São Miguel that include hotel bookings?

    Yes. In addition to deals on Chicago to São Miguel flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to São Miguel?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to São Miguel.

  • Can I find deals for business class flights from Chicago to São Miguel?

    Yes. Cheapflights offers flight deals from Chicago to São Miguel by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to São Miguel

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Ponta Delgada flights
Midway to Ponta Delgada flights
O'Hare Intl to Lajes flights
St. Louis to Lajes flights

Top 2 airlines flying from Chicago to São Miguel

Discover the top 2 airlines that operate flights from Chicago to São Miguel. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$549Average$939FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$716Average$1,200FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.