HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
São Miguel

$412+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
jul. 1 — jul. 81
mar. 7/1
mar. 7/8
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.

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 junio 26, 2025.

Round-trip from

$550
(TAP AIR PORTUGAL)

One-way from

$412
(Mytrip)

Popular in

May

Cheapest in

October

Average price

$1,166
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 ($202 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 junio 26, 2025.

This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/24. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/116:10 pmORD - PDL
1 stop15h 45mTAP AIR PORTUGAL
mié. 8/207:30 pmPDL - ORD
1 stop22h 05mTAP AIR PORTUGAL
Deal found 6/24$550
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/184:50 pmORD - PDL
1 stop10h 50mUnited Airlines
mié. 9/2411:00 amPDL - ORD
2 stops15h 16mUnited Airlines
Deal found 6/26$620
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
sáb. 10/186:15 pmORD - PDL
1 stop13h 05mMultiple Airlines
vie. 10/246:30 amPDL - ORD
1 stop14h 40mMultiple Airlines
Deal found 6/26$690
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
lun. 10/69:15 amMDW - PDL
1 stop16h 25mMultiple Airlines
mié. 10/155:30 pmPDL - MDW
2 stops29h 48mMultiple Airlines
Deal found 6/26$938

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 junio 26, 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

lun. 8/11

6:10 pm-2:55 pm

1 stop15h 45m

Ponta Delgada Nordela

mié. 8/20

7:30 pm-12:35 pm

1 stop22h 05m

$550

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

jue. 9/18

4:50 pm-8:40 am

1 stop10h 50m

Ponta Delgada Nordela

mié. 9/24

11:00 am-9:16 pm

2 stops15h 16m

$620

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

dom. 8/24

7:05 pm-9:45 am

3 stops33h 40m

Ponta Delgada Nordela

dom. 8/31

6:30 am-12:55 pm

3 stops35h 25m

$987

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

dom. 8/24

9:40 am-9:45 am

3 stops19h 05m

Ponta Delgada Nordela

dom. 8/31

6:30 am-9:50 am

3 stops32h 20m

$1,157

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

jue. 8/28

12:05 pm-6:50 pm

3 stops25h 45m

$412

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

lun. 7/7

6:10 pm-6:35 pm

1 stop19h 25m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

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 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 $984). 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.

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 junio 26, 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 junio 26, 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
8,838 reviews

Entertainment

7.0

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,838 reviews
United Airlines
7.4
Good
8,838 reviews

Entertainment

7.0

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
TAP AIR PORTUGAL
7.1
Good
1,903 reviews
United Airlines
7.4
Good
8,838 reviews

Entertainment

7.0

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • 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 $984). 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

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 junio 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$549Average$954FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$720Average$1,201FlexibilityNo 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.