What is the cheapest airline that flies from Chicago to São Miguel?

TAP AIR PORTUGAL and United Airlines are the most popular carriers operating from Chicago to São Miguel

When did momondo last update prices for flights from Chicago to São Miguel?

Prices for flights from Chicago to São Miguel are updated daily.

How many operators does momondo search for flights from Chicago to São Miguel?

As of March 2026, there are 2 operators available to choose from for flights from Chicago to São Miguel.

How old do you have to be to fly from Chicago to São Miguel?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to São Miguel.

What documentation or ID do you need to fly to São Miguel?

The necessary travel and health documents for your São Miguel trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$389 Cheap Flights from Chicago to São Miguel in 2026

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Find the cheapest flights from Chicago to São Miguel

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 11:45 pm

ORD

PDL

24h 45m

1 stop

7:40 pm - 4:00 pm

PDL

ORD

25h 20m

1 stop

$646TAP AIR PORTUGAL

Fri, Apr 24 - Tue, Apr 28

6:00 pm - 6:50 pm

ORD

PDL

19h 50m

1 stop

6:30 am - 4:00 pm

PDL

ORD

14h 30m

1 stop

$656TAP AIR PORTUGAL

Wed, Apr 15 - Wed, Apr 22

6:00 pm - 11:45 pm

ORD

PDL

24h 45m

1 stop

6:30 am - 4:05 pm

PDL

ORD

14h 35m

1 stop

$666TAP AIR PORTUGAL

Fri, Apr 10 - Sat, Apr 18

9:25 pm - 8:15 am

ORD

PDL

30h 50m

1 stop

10:45 am - 4:00 pm

PDL

ORD

34h 15m

1 stop

$671TAP AIR PORTUGAL

Sun, Mar 22 - Tue, Apr 7

9:25 pm - 8:15 am

ORD

PDL

30h 50m

1 stop

3:45 pm - 4:00 pm

PDL

ORD

29h 15m

1 stop

$704TAP AIR PORTUGAL

Sun, Mar 22 - Tue, Mar 31

6:00 pm - 6:50 pm

ORD

PDL

19h 50m

1 stop

6:30 am - 4:00 pm

PDL

ORD

14h 30m

1 stop

$706TAP AIR PORTUGAL

Wed, Apr 22 - Sun, Apr 26

6:20 pm - 6:20 am

ORD

PDL

31h 00m

1 stop

8:15 pm - 8:08 am

PDL

ORD

40h 53m

2 stops

$709Multiple Airlines

Mon, Mar 30 - Mon, Apr 6

9:25 pm - 8:15 am

ORD

PDL

30h 50m

1 stop

6:30 am - 4:00 pm

PDL

ORD

14h 30m

1 stop

$738TAP AIR PORTUGAL

Sun, Mar 22 - Wed, Apr 1

9:41 am - 6:20 am

ORD

PDL

15h 39m

1 stop

5:30 pm - 7:41 am

PDL

ORD

19h 11m

1 stop

$749Multiple Airlines

Tue, Apr 14 - Mon, Apr 20

1:05 pm - 9:05 am

MDW

PDL

15h 00m

2 stops

9:35 am - 8:42 am

PDL

MDW

28h 07m

2 stops

$1,154WestJet

Mon, Aug 10 - Mon, Aug 17

TAP AIR PORTUGAL flights from Chicago to São Miguel

Our best TAP AIR PORTUGAL deals on Chicago to São Miguel flight tickets

TAP AIR PORTUGAL

Apr 24

ORD6:00 pmChicago O'Hare Intl

24h 45m

1 stop

PDL11:45 pmPonta Delgada Nordela

Apr 28

PDL7:40 pmPonta Delgada Nordela

25h 20m

1 stop

ORD4:00 pmChicago O'Hare Intl

$646

TAP AIR PORTUGAL

Apr 15

ORD6:00 pmChicago O'Hare Intl

19h 50m

1 stop

PDL6:50 pmPonta Delgada Nordela

Apr 22

PDL6:30 amPonta Delgada Nordela

14h 30m

1 stop

ORD4:00 pmChicago O'Hare Intl

$656

TAP AIR PORTUGAL

Apr 10

ORD6:00 pmChicago O'Hare Intl

24h 45m

1 stop

PDL11:45 pmPonta Delgada Nordela

Apr 18

PDL6:30 amPonta Delgada Nordela

14h 35m

1 stop

ORD4:05 pmChicago O'Hare Intl

$666

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 4/24

6:00 pm-11:45 pm

1 stop24h 45m

Ponta Delgada Nordela

Tue 4/28

7:40 pm-4:00 pm

1 stop25h 20m

$646

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 4/15

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

Wed 4/22

6:30 am-4:00 pm

1 stop14h 30m

$656

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 4/10

6:00 pm-11:45 pm

1 stop24h 45m

Ponta Delgada Nordela

Sat 4/18

6:30 am-4:05 pm

1 stop14h 35m

$666

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 3/22

9:25 pm-8:15 am

1 stop30h 50m

Ponta Delgada Nordela

Tue 4/7

10:45 am-4:00 pm

1 stop34h 15m

$671

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 3/22

9:25 pm-8:15 am

1 stop30h 50m

Ponta Delgada Nordela

Tue 3/31

3:45 pm-4:00 pm

1 stop29h 15m

$704

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 4/22

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

Sun 4/26

6:30 am-4:00 pm

1 stop14h 30m

$706

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Mon 3/30

6:20 pm-6:20 am

1 stop31h 00m

Ponta Delgada Nordela

Mon 4/6

8:15 pm-8:08 am

2 stops40h 53m

$709

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 3/22

9:25 pm-8:15 am

1 stop30h 50m

Ponta Delgada Nordela

Wed 4/1

6:30 am-4:00 pm

1 stop14h 30m

$738

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Tue 4/14

9:41 am-6:20 am

1 stop15h 39m

Ponta Delgada Nordela

Mon 4/20

5:30 pm-7:41 am

1 stop19h 11m

$749

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Mon 8/10

1:05 pm-9:05 am

2 stops15h 00m

Ponta Delgada Nordela

Mon 8/17

9:35 am-8:42 am

2 stops28h 07m

$1,154

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to São Miguel

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on Chicago to São Miguel flights?

No. A direct flight is the cheapest option for a flight between Chicago to São Miguel.

Cheap Chicago to São Miguel flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to São Miguel

Fastest flight time	12h 40m
Direct flights	None

The fastest flight from Chicago to São Miguel takes 12h 40m

There are no direct flights from Chicago to São Miguel. There are no popular flight routes from Chicago to São Miguel.

Search flight deals

When did momondo last update prices for flights from Chicago to São Miguel?
Prices for flights from Chicago to São Miguel are updated daily.
How many operators does momondo search for flights from Chicago to São Miguel?
As of March 2026, there are 2 operators available to choose from for flights from Chicago to São Miguel.
How old do you have to be to fly from Chicago to São Miguel?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to São Miguel.
What documentation or ID do you need to fly to São Miguel?
The necessary travel and health documents for your São Miguel trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to São Miguel?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to São Miguel is Airbus A321neo (16.96% of total bookings). The next most popular plane models are Boeing 737-800 (15.95%), Boeing 737-900 (7.58%), and Airbus A321-100/200 (7.52%).

Best airlines flying from Chicago to São Miguel

Compare and see reviews for airlines that fly from Chicago to São Miguel with momondo

Airline	Rating	Free Cancellation	Price
TAP AIR PORTUGAL	PriceFrom $550	Free Cancellation	Rating 7.1 2,155 reviews		Search TAP AIR PORTUGAL flights
United Airlines	PriceFrom $716	Free Cancellation	Rating 7.4 9,375 reviews		Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to São Miguel?

Finding the right flight to São Miguel from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to São Miguel quick and easy, saving you time and money.

Can I find flights from Chicago to São Miguel with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to São Miguel flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to São Miguel?

momondo helps you find the best flight between Chicago and São Miguel by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to São Miguel right now. Can momondo alert me if prices change?

Price alerts on flights to São Miguel from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.