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São Miguel

$308+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$527
(oojo)

One-way from

$308
(FlightHub)

Popular in

May

Cheapest in

October

Average price

$959
From Chicago (CHI) to São Miguel
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One-way flight from Chicago (CHI) to São Miguel
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Highest demand for flights based on searches. 14% potential increase in price ($168 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This oojo deal was found by Cheapflights users on 9/15. 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 stop22h 30mTAP AIR PORTUGAL
Fri 12/56:30 amPDL - ORD
1 stop13h 45mTAP AIR PORTUGAL
Deal found 9/15$527
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/711:13 amORD - PDL
2 stops31h 32mMultiple Airlines
Tue 10/215:30 pmPDL - ORD
1 stop24h 15mMultiple Airlines
Deal found 9/15$692
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:40 amORD - PDL
2 stops31h 10mMultiple Airlines
Wed 10/295:20 pmPDL - ORD
1 stop23h 25mMultiple Airlines
Deal found 9/16$711
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:40 amORD - PDL
2 stops26h 55mMultiple Airlines
Wed 10/295:20 pmPDL - ORD
1 stop23h 25mMultiple Airlines
Deal found 9/16$745
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Sun 10/57:25 pmORD - PDL
3 stops33h 20mMultiple Airlines
Fri 10/177:50 amPDL - ORD
2 stops18h 25mMultiple Airlines
Deal found 9/16$754
This oojo deal was found by Cheapflights users on 9/16. 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 stops30h 35mTAP AIR PORTUGAL
Tue 12/97:25 pmPDL - ORD
1 stop24h 35mTAP AIR PORTUGAL
Deal found 9/16$755
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/611:13 amORD - PDL
2 stops22h 32mMultiple Airlines
Tue 10/215:30 pmPDL - ORD
1 stop24h 15mMultiple Airlines
Deal found 9/15$763
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:15 pmORD - PDL
1 stop19h 35mTAP AIR PORTUGAL
Sat 10/257:35 pmPDL - ORD
1 stop25h 10mTAP AIR PORTUGAL
Deal found 9/16$770
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 9/186:00 pmORD - PDL
1 stop14h 35mTAP AIR PORTUGAL
Wed 9/247:30 pmPDL - ORD
1 stop22h 05mTAP AIR PORTUGAL
Deal found 9/15$790
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Sun 10/59:35 amMDW - PDL
2 stops21h 10mMultiple Airlines
Fri 10/174:55 pmPDL - MDW
2 stops22h 35mMultiple Airlines
Deal found 9/15$1,524
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/219:35 amMDW - PDL
2 stops31h 30mMultiple Airlines
Tue 9/234:55 pmPDL - MDW
1 stop28h 29mMultiple Airlines
Deal found 9/17$1,665

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 September 17, 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 11/28

8:15 pm-11:45 pm

1 stop22h 30m

Ponta Delgada Nordela

Fri 12/5

6:30 am-3:15 pm

1 stop13h 45m

$527

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 10/22

6:40 am-6:50 pm

2 stops31h 10m

Ponta Delgada Nordela

Wed 10/29

5:20 pm-12:45 pm

1 stop23h 25m

$711

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 10/19

6:00 pm-11:45 pm

1 stop24h 45m

Ponta Delgada Nordela

Wed 10/29

6:35 am-4:00 pm

1 stop13h 25m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 10/19

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

Tue 10/28

7:25 pm-4:00 pm

1 stop24h 35m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 10/19

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

Thu 10/23

7:40 pm-4:10 pm

1 stop25h 30m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 10/22

6:40 am-6:45 am

1 stop19h 05m

Ponta Delgada Nordela

Sun 10/26

5:55 pm-1:03 am

2 stops35h 08m

$835

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 10/18

6:15 pm-2:35 pm

1 stop15h 20m

Ponta Delgada Nordela

Tue 10/28

7:25 pm-4:00 pm

1 stop24h 35m

$837

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 10/19

6:00 pm-3:00 pm

1 stop16h 00m

Ponta Delgada Nordela

Fri 10/24

7:40 pm-4:30 pm

1 stop25h 50m

$837

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 10/18

6:15 pm-9:45 am

1 stop34h 30m

Ponta Delgada Nordela

Thu 10/23

7:40 pm-4:10 pm

1 stop25h 30m

$837

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Thu 10/16

6:00 pm-2:40 pm

1 stop15h 40m

Ponta Delgada Nordela

Tue 10/28

5:55 pm-9:33 pm

2 stops31h 38m

$851

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 24 results
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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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to São Miguel as you normally would.

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 September 17, 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
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
TAP AIR PORTUGAL
7.1
Good
1,977 reviews
United Airlines
7.4
Good
8,926 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

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 22h 30m. 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.

  • What is the cheapest month to book a flight from Chicago to São Miguel?

    Currently, January is the cheapest month in which you can book a flight from Chicago to São Miguel (average of $518). Flying from Chicago to São Miguel in June is currently the most expensive (average of $988). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$549Average$944FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$716Average$1,179FlexibilityNo cancel feeOn-time69%

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