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$585+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$692
(United Airlines)

One-way from

$585
(oojo)

Popular in

May

Cheapest in

February

Average price

$1,185
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. 16% potential increase in price ($195 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($47 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/89:18 amORD - PDL
1 stop16h 37mMultiple Airlines
Sat 11/155:20 pmPDL - ORD
1 stop18h 53mMultiple Airlines
Deal found 7/30$683
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:31 pmORD - PDL
2 stops30h 09mUnited Airlines
Sun 9/2111:00 amPDL - ORD
1 stop11h 05mUnited Airlines
Deal found 7/30$692
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Sun 12/288:25 pmORD - PDL
1 stop17h 10mTAP AIR PORTUGAL
Sat 1/107:25 pmPDL - ORD
1 stop24h 35mTAP AIR PORTUGAL
Deal found 7/29$735
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Fri 8/156:00 pmORD - TER
1 stop13h 50mTAP AIR PORTUGAL
Fri 8/297:10 amTER - ORD
1 stop14h 00mTAP AIR PORTUGAL
Deal found 7/29$911
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Wed 9/179:20 amMDW - PDL
2 stops16h 20mMultiple Airlines
Sun 9/218:35 amPDL - MDW
2 stops12h 49mMultiple Airlines
Deal found 7/30$1,015
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Wed 8/138:12 pmORD - TER
3 stops35h 43mMultiple Airlines
Fri 8/297:10 amTER - ORD
1 stop14h 00mMultiple Airlines
Deal found 7/30$1,194

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 July 31, 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

Wed 9/17

9:31 pm-8:40 am

2 stops30h 09m

Ponta Delgada Nordela

Sun 9/21

11:00 am-5:05 pm

1 stop11h 05m

$692

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 9/13

4:35 pm-2:35 pm

2 stops17h 00m

Ponta Delgada Nordela

Fri 9/26

5:30 pm-4:50 pm

1 stop28h 20m

$696

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 9/13

6:15 pm-2:35 pm

1 stop15h 20m

Ponta Delgada Nordela

Fri 9/26

6:30 am-4:30 pm

1 stop15h 00m

$765

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Sun 8/10

6:00 pm-11:15 pm

1 stop24h 15m

Lajes

Sun 8/31

1:40 pm-4:40 pm

1 stop32h 00m

$819

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Wed 9/17

9:20 am-6:40 am

2 stops16h 20m

Ponta Delgada Nordela

Sun 9/21

8:35 am-4:24 pm

2 stops12h 49m

$1,015

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Wed 8/13

8:12 pm-12:55 pm

3 stops35h 43m

Lajes

Fri 8/29

7:10 am-4:10 pm

1 stop14h 00m

$1,194

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 9/24

1:37 pm-6:50 pm

2 stops24h 13m

$585

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Wed 9/24

6:15 pm-4:05 pm

2 stops16h 50m

$5,810

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 9/24

5:10 pm-4:05 pm

1 stop17h 55m

$6,155

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 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 $987). 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 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 July 31, 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.

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 July 31, 2025.
Read reviews from past customers who have flown Air France, 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.
Air France
7.5
Good
1,465 reviews

Overall

7.5

Comfort

7.4

Crew

8.1

Boarding

7.4

Food

7.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

SYLVIA,Apr 2025

TLV - CDG

A newer plane. The flight from TelAviv to Paris was on a new aircraft, wider seat. ,more privacy. Nice toilets. The flight from Paris to Santiago Chile was on a very old aircraft. Awful toilets, outmoded sits etc.
Air France
7.5
Good
1,465 reviews
Air France
7.5
Good
1,465 reviews

Overall

7.5

Comfort

7.4

Crew

8.1

Boarding

7.4

Food

7.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

SYLVIA,Apr 2025

TLV - CDG

A newer plane. The flight from TelAviv to Paris was on a new aircraft, wider seat. ,more privacy. Nice toilets. The flight from Paris to Santiago Chile was on a very old aircraft. Awful toilets, outmoded sits etc.
United Airlines
7.4
Good
8,900 reviews
Air France
7.5
Good
1,465 reviews

Overall

7.5

Comfort

7.4

Crew

8.1

Boarding

7.4

Food

7.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

SYLVIA,Apr 2025

TLV - CDG

A newer plane. The flight from TelAviv to Paris was on a new aircraft, wider seat. ,more privacy. Nice toilets. The flight from Paris to Santiago Chile was on a very old aircraft. Awful toilets, outmoded sits etc.
TAP AIR PORTUGAL
7.1
Good
1,933 reviews
Air France
7.5
Good
1,465 reviews

Overall

7.5

Comfort

7.4

Crew

8.1

Boarding

7.4

Food

7.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

SYLVIA,Apr 2025

TLV - CDG

A newer plane. The flight from TelAviv to Paris was on a new aircraft, wider seat. ,more privacy. Nice toilets. The flight from Paris to Santiago Chile was on a very old aircraft. Awful toilets, outmoded sits etc.

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.

  • 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 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 $987). 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$549Average$885FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$719Average$1,200FlexibilityNo cancel feeOn-time69%

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