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Azores

$424+ Cheap flights from Chicago (CHI) to Azores

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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
May 3 — May 101
Sun 5/3
Sun 5/10
1 adult, Economy
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Cheap flight deals from Chicago to Azores

Cheapest flights from Chicago to Azores
Explore the most affordable flight options available from Chicago to Azores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2026.

This Gotogate deal was found by Cheapflights users on 4/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 pm
ORD
-
PDL
1 stop15h 30m
TAP AIR PORTUGAL
Fri 4/176:30 am
PDL
-
ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 4/2$761
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:05 pm
ORD
-
TER
1 stop13h 45m
TAP AIR PORTUGAL
Fri 4/247:10 am
TER
-
ORD
1 stop13h 50m
TAP AIR PORTUGAL
Deal found 4/2$775
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 pm
ORD
-
PDL
1 stop16h 00m
TAP AIR PORTUGAL
Tue 4/287:40 pm
PDL
-
ORD
1 stop25h 20m
TAP AIR PORTUGAL
Deal found 4/2$781
This TAP AIR PORTUGAL deal was found by Cheapflights users on 4/1. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:15 pm
ORD
-
PDL
1 stop17h 20m
TAP AIR PORTUGAL
Thu 12/37:25 pm
PDL
-
ORD
1 stop25h 05m
TAP AIR PORTUGAL
Deal found 4/1$782
This oojo deal was found by Cheapflights users on 4/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 pm
ORD
-
TER
1 stop24h 15m
TAP AIR PORTUGAL
Sat 10/247:05 am
TER
-
ORD
1 stop14h 00m
TAP AIR PORTUGAL
Deal found 4/1$791
This FlightHub deal was found by Cheapflights users on 4/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:05 pm
ORD
-
PDL
1 stop24h 40m
TAP AIR PORTUGAL
Sun 4/266:30 am
PDL
-
ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 4/2$809
This FlightHub deal was found by Cheapflights users on 3/30. 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.
Wed 9/236:00 pm
ORD
-
TER
1 stop13h 55m
TAP AIR PORTUGAL
Fri 10/27:10 am
TER
-
ORD
1 stop13h 50m
TAP AIR PORTUGAL
Deal found 3/30$815
This KAYAK deal was found by Cheapflights users on 4/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:05 pm
ORD
-
PDL
1 stop24h 40m
TAP AIR PORTUGAL
Thu 4/237:40 pm
PDL
-
ORD
1 stop25h 20m
TAP AIR PORTUGAL
Deal found 4/2$817
This oojo deal was found by Cheapflights users on 3/30. 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.
Wed 9/236:00 pm
ORD
-
TER
1 stop24h 15m
TAP AIR PORTUGAL
Sat 10/37:05 am
TER
-
ORD
1 stop14h 00m
TAP AIR PORTUGAL
Deal found 3/30$821
This Mytrip deal was found by Cheapflights users on 3/30. 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 5/269:55 am
ORD
-
PDL
2 stops32h 50m
Multiple Airlines
Tue 6/23:45 pm
PDL
-
ORD
2 stops32h 40m
Multiple Airlines
Deal found 3/30$821
This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:55 am
ORD
-
PDL
2 stops24h 10m
Multiple Airlines
Tue 4/284:55 pm
PDL
-
ORD
2 stops22h 58m
Multiple Airlines
Deal found 3/31$825
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:00 pm
ORD
-
PDL
1 stop19h 45m
TAP AIR PORTUGAL
Sat 5/96:30 am
PDL
-
ORD
1 stop14h 35m
TAP AIR PORTUGAL
Deal found 4/1$826

Find flight deals from Chicago to Azores

Keep the following information in mind while searching for Chicago to Azores flight deals. Data was last updated April 3, 2026.

Round-trip from

$745
(oojo)

One-way from

$424
(oojo)

Popular in

May

Cheapest in

January

Average price

$742
From Chicago (CHI) to Azores
Search Deals
One-way flight from Chicago (CHI) to Azores
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($173 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Azores 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 April 3, 2026.
Use the filters below to find and compare flights from Chicago to Azores that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 5/2

6:05 pm-2:35 pm

1 stop15h 30m

Ponta Delgada Nordela

Sat 5/9

6:30 am-4:05 pm

1 stop14h 35m

$842

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Wed 9/30

6:00 pm-12:55 pm

1 stop13h 55m

Lajes

Thu 10/8

1:50 pm-4:00 pm

1 stop31h 10m

$915

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Sun 4/19

6:00 pm-12:50 pm

1 stop13h 50m

Lajes

Sat 4/25

1:40 pm-4:00 pm

1 stop31h 20m

$922

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Wed 9/23

6:00 pm-11:15 pm

1 stop24h 15m

Lajes

Thu 10/1

1:50 pm-4:00 pm

1 stop31h 10m

$930

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Fri 9/25

6:00 pm-11:15 pm

1 stop24h 15m

Lajes

Fri 10/2

7:10 am-4:00 pm

1 stop13h 50m

$943

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Fri 9/25

6:00 pm-12:50 pm

1 stop13h 50m

Lajes

Sun 10/4

7:10 am-4:00 pm

1 stop13h 50m

$963

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 8/9

8:40 am-8:40 am

2 stops19h 00m

Ponta Delgada Nordela

Tue 8/25

11:00 am-6:37 pm

1 stop12h 37m

$981

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Sun 6/14

10:25 am-8:10 am

1 stop16h 45m

Ponta Delgada Nordela

Sun 6/21

9:20 pm-9:40 am

2 stops41h 20m

$1,032
Quickest round-trip

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sun 8/9

4:40 pm-8:40 am

1 stop11h 00m

Ponta Delgada Nordela

Sun 8/23

9:35 am-2:55 pm

1 stop10h 20m

$1,034

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 8/7

6:22 pm-8:20 am

2 stops32h 58m

Ponta Delgada Nordela

Fri 8/28

9:35 am-9:00 am

1 stop28h 25m

$1,038

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 37 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Azores

Have a flexible travel schedule? Discover the best time to fly to Azores 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 Azores

How much does it cost to fly round-trip from Chicago to Azores?

Reviews of airlines servicing Azores

Get insights into the airlines that provide service to Azores. 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 Azores. Reviews last updated April 3, 2026.
Read reviews from past customers who have flown United Airlines and TAP AIR PORTUGAL from Chicago to Azores. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,535 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,535 reviews
United Airlines
7.4
Good
9,535 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
TAP AIR PORTUGAL
7.1
Good
2,187 reviews
United Airlines
7.4
Good
9,535 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Chicago to Azores. 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 Azores?

    Departing from Chicago to Azores will take you 15h 30m. The distance between Chicago and Azores is about 3237 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago to Azores?

    Most travelers choose Chicago O'Hare Intl - Ponta Delgada Nordela, Chicago O'Hare Intl - Lajes or Chicago Midway - Ponta Delgada Nordela when deciding on the best route from Chicago to Azores.

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

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

  • How can I find direct flights from Chicago to Azores?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Azores 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

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Top 2 airlines flying from Chicago to Azores

Discover the top 2 airlines that operate flights from Chicago to Azores. 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 April 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$550Average$893FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$716Average$1,027FlexibilityNo cancel feeOn-time69%

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