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$308+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
oct. 16 — oct. 231
jeu. 10/16
jeu. 10/23
1 adult, Economy
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Cheap flight deals from Chicago to Azores

Keep the following information in mind while searching for Chicago to Azores flight deals. Data was last updated septembre 16, 2025.

Round-trip from

$527
(oojo)

One-way from

$308
(FlightHub)

Popular in

May

Cheapest in

October

Average price

$959
From Chicago (CHI) to Azores
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One-way flight from Chicago (CHI) to Azores
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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 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 septembre 16, 2025.

This oojo deal was found by Cheapflights users on 9/14. 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.
ven. 11/288:15 pmORD - PDL
1 stop31h 10mTAP AIR PORTUGAL
ven. 12/56:30 amPDL - ORD
1 stop13h 45mTAP AIR PORTUGAL
Deal found 9/14$527
This Mytrip deal was found by Cheapflights users on 9/13. 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.
mer. 10/2912:50 pmORD - PDL
3 stops25h 45mMultiple Airlines
mer. 11/57:25 pmPDL - ORD
3 stops29h 35mMultiple Airlines
Deal found 9/13$683
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
mar. 10/711:13 amORD - PDL
2 stops31h 32mMultiple Airlines
mar. 10/215:30 pmPDL - ORD
1 stop24h 15mMultiple Airlines
Deal found 9/13$684
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.
mer. 10/226:40 amORD - PDL
2 stops31h 10mMultiple Airlines
mer. 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.
sam. 10/186:40 amORD - PDL
2 stops26h 55mMultiple Airlines
mer. 10/295:20 pmPDL - ORD
1 stop23h 25mMultiple Airlines
Deal found 9/16$745
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jeu. 9/186:00 pmORD - PDL
1 stop14h 35mTAP AIR PORTUGAL
mer. 9/247:30 pmPDL - ORD
1 stop22h 05mTAP AIR PORTUGAL
Deal found 9/14$751
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.
dim. 10/57:25 pmORD - PDL
3 stops33h 20mMultiple Airlines
ven. 10/177:50 amPDL - ORD
2 stops18h 25mMultiple Airlines
Deal found 9/16$754
This oojo deal was found by Cheapflights users on 9/13. 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.
mer. 10/2911:20 amORD - PDL
2 stops17h 00mTAP AIR PORTUGAL
mer. 11/56:35 amPDL - ORD
1 stop13h 25mTAP AIR PORTUGAL
Deal found 9/13$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.
lun. 10/611:13 amORD - PDL
2 stops22h 32mMultiple Airlines
mar. 10/215:30 pmPDL - ORD
1 stop24h 15mMultiple Airlines
Deal found 9/15$763
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.
dim. 10/59:35 amMDW - PDL
2 stops21h 10mMultiple Airlines
ven. 10/174:55 pmPDL - MDW
2 stops22h 35mMultiple Airlines
Deal found 9/15$1,524

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 septembre 16, 2025.
Use the filters below to find and compare flights from Chicago to Azores that are best for you.

Fly from

Chicago

Fly to

Azores

Route

Depart

Return

Price

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

ven. 11/28

8:15 pm-8:25 am

1 stop31h 10m

Ponta Delgada Nordela

ven. 12/5

6:30 am-3:15 pm

1 stop13h 45m

$527

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

ven. 3/13

9:15 pm-6:35 pm

1 stop17h 20m

Ponta Delgada Nordela

dim. 3/22

6:30 am-3:45 pm

1 stop13h 15m

$598

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

sam. 10/18

6:40 am-2:35 pm

2 stops26h 55m

Ponta Delgada Nordela

mer. 10/29

5:20 pm-12:45 pm

1 stop23h 25m

$745

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

lun. 10/6

11:13 am-2:45 pm

2 stops22h 32m

Ponta Delgada Nordela

mar. 10/21

5:30 pm-12:45 pm

1 stop24h 15m

$754

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

dim. 10/5

6:00 pm-11:45 pm

1 stop24h 45m

Ponta Delgada Nordela

mar. 10/21

7:25 pm-4:10 pm

1 stop25h 45m

$787

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

sam. 10/4

11:12 am-11:45 pm

2 stops31h 33m

Ponta Delgada Nordela

mar. 10/21

5:30 pm-12:45 pm

1 stop24h 15m

$803

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

dim. 10/19

6:00 pm-11:45 pm

1 stop24h 45m

Ponta Delgada Nordela

mer. 10/29

6:35 am-4:00 pm

1 stop13h 25m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

dim. 10/19

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

mar. 10/28

7:25 pm-4:00 pm

1 stop24h 35m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

dim. 10/19

6:00 pm-6:50 pm

1 stop19h 50m

Ponta Delgada Nordela

jeu. 10/23

7:40 pm-4:10 pm

1 stop25h 30m

$817

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

sam. 10/18

6:15 pm-2:35 pm

1 stop15h 20m

Ponta Delgada Nordela

mar. 10/28

7:25 pm-4:00 pm

1 stop24h 35m

$837

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 results
1
2

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

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

Find hourly flight availability from Chicago to Azores. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 16, 2025.

When flying from Chicago to Azores, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 septembre 16, 2025.
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
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

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
1,975 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

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 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 31h 10m. The distance between Chicago and Azores is about 3237 mi.

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

    Most travelers choose Chicago O'Hare Intl - Ponta Delgada Nordela, Chicago Midway - Ponta Delgada Nordela or Chicago O'Hare Intl - Horta 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Azores (average of $518). Flying from Chicago to Azores 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

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 septembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$549Average$879FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$716Average$1,179FlexibilityNo cancel feeOn-time69%

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