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Azores

$309+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDL
Jul 10 — Jul 171
Fri 7/10
Fri 7/17
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 June 10, 2026.

This oojo deal was found by Cheapflights users on 6/9. 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 11/47:00 pm
ORD
-
PDL
1 stop18h 35m
TAP AIR PORTUGAL
Fri 11/136:30 am
PDL
-
ORD
1 stop14h 00m
TAP AIR PORTUGAL
Deal found 6/9$766
This FlightHub deal was found by Cheapflights users on 6/8. 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 11/47:00 pm
ORD
-
TER
1 stop23h 15m
TAP AIR PORTUGAL
Thu 11/1211:50 am
TER
-
ORD
1 stop32h 40m
TAP AIR PORTUGAL
Deal found 6/8$772
This FlightHub deal was found by Cheapflights users on 6/8. 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 11/47:00 pm
ORD
-
TER
1 stop23h 15m
TAP AIR PORTUGAL
Sat 11/1411:50 am
TER
-
ORD
1 stop32h 40m
TAP AIR PORTUGAL
Deal found 6/8$792
This FlightHub deal was found by Cheapflights users on 6/9. 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 11/47:00 pm
ORD
-
PDL
1 stop23h 45m
TAP AIR PORTUGAL
Thu 11/127:25 pm
PDL
-
ORD
1 stop25h 05m
TAP AIR PORTUGAL
Deal found 6/9$795
This Justfly.com deal was found by Cheapflights users on 6/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:10 pm
ORD
-
PDL
1 stop31h 10m
TAP AIR PORTUGAL
Tue 11/177:25 pm
PDL
-
ORD
1 stop25h 05m
TAP AIR PORTUGAL
Deal found 6/7$796
This FlightHub deal was found by Cheapflights users on 6/9. 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 11/47:00 pm
ORD
-
PDL
1 stop18h 35m
TAP AIR PORTUGAL
Sat 11/147:25 pm
PDL
-
ORD
1 stop25h 05m
TAP AIR PORTUGAL
Deal found 6/9$815
This Justfly.com deal was found by Cheapflights users on 6/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:10 pm
ORD
-
PDL
1 stop17h 25m
TAP AIR PORTUGAL
Sun 11/156:30 am
PDL
-
ORD
1 stop14h 00m
TAP AIR PORTUGAL
Deal found 6/7$816
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Fri 11/68:10 pm
ORD
-
PDL
1 stop17h 25m
TAP AIR PORTUGAL
Wed 11/116:30 am
PDL
-
ORD
1 stop14h 00m
TAP AIR PORTUGAL
Deal found 6/9$823
This FlightHub deal was found by Cheapflights users on 6/8. 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 10/146:00 pm
ORD
-
TER
1 stop24h 15m
TAP AIR PORTUGAL
Fri 10/237:10 am
TER
-
ORD
1 stop13h 50m
TAP AIR PORTUGAL
Deal found 6/8$824
This FlightHub deal was found by Cheapflights users on 6/8. 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 10/146:00 pm
ORD
-
TER
1 stop13h 55m
TAP AIR PORTUGAL
Thu 10/221:50 pm
TER
-
ORD
1 stop31h 10m
TAP AIR PORTUGAL
Deal found 6/8$831
This Mytrip deal was found by Cheapflights users on 6/9. 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 9/28:45 am
ORD
-
PDL
2 stops18h 25m
Multiple Airlines
Mon 9/147:40 pm
PDL
-
ORD
2 stops30h 55m
Multiple Airlines
Deal found 6/9$838
This oojo deal was found by Cheapflights users on 6/8. 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 10/146:00 pm
ORD
-
PDL
1 stop19h 50m
TAP AIR PORTUGAL
Fri 10/236:30 am
PDL
-
ORD
1 stop14h 30m
TAP AIR PORTUGAL
Deal found 6/8$841

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 June 10, 2026.

Round-trip from

$766
(oojo)

One-way from

$309
(Mytrip)

Popular in

May

Cheapest in

January

Average price

$1,095
From Chicago (CHI) to Azores
Search Deals
One-way flight from Chicago (CHI) to Azores
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 10, 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

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Fri 10/23

6:00 pm-11:15 pm

1 stop24h 15m

Lajes

Fri 10/30

6:40 am-4:30 pm

1 stop13h 50m

$945

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 10/24

6:05 pm-12:45 am

1 stop25h 40m

Ponta Delgada Nordela

Wed 10/28

6:30 am-4:30 pm

1 stop14h 00m

$956

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 10/16

6:00 pm-3:00 pm

1 stop16h 00m

Ponta Delgada Nordela

Thu 10/29

7:25 pm-4:30 pm

1 stop25h 05m

$957

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Sat 10/24

6:05 pm-12:45 am

1 stop25h 40m

Ponta Delgada Nordela

Sat 10/31

7:25 pm-4:30 pm

1 stop25h 05m

$976

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Fri 10/16

6:00 pm-3:00 pm

1 stop16h 00m

Ponta Delgada Nordela

Sat 10/24

6:30 am-4:05 pm

1 stop14h 35m

$977

ChicagoLajes

ORD - TER

ORDTER

Chicago O'Hare Intl

Mon 11/2

1:00 pm-11:00 am

2 stops41h 00m

Lajes

Fri 11/13

6:40 am-3:30 pm

1 stop13h 50m

$1,034

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Mon 11/2

1:00 pm-6:35 pm

2 stops24h 35m

Ponta Delgada Nordela

Fri 11/13

6:30 am-3:30 pm

1 stop14h 00m

$1,046
Quickest round-trip

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Wed 7/8

3:00 pm-8:40 am

2 stops12h 40m

Ponta Delgada Nordela

Tue 7/14

11:00 am-6:50 pm

2 stops12h 50m

$1,108

ChicagoPonta Delgada

ORD - PDL

ORDPDL

Chicago O'Hare Intl

Thu 10/22

1:00 pm-11:45 pm

2 stops29h 45m

Ponta Delgada Nordela

Wed 10/28

6:30 am-4:30 pm

1 stop14h 00m

$1,141

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Wed 8/5

10:20 am-8:10 am

1 stop16h 50m

Ponta Delgada Nordela

Wed 8/19

7:30 pm-9:40 am

2 stops43h 10m

$1,150

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 36 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

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

Currently, April is the cheapest month in which you can book a flight from Chicago to Azores (average of $469). Flying from Chicago to Azores in November is currently the most expensive (average of $1,030). 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.

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 June 10, 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
9,808 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,808 reviews
United Airlines
7.4
Good
9,808 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
TAP AIR PORTUGAL
7.2
Good
2,274 reviews
United Airlines
7.4
Good
9,808 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 22h 55m. The distance between Chicago and Azores is about 3139 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 Midway - Ponta Delgada Nordela or Chicago O'Hare Intl - Lajes 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, April is the cheapest month in which you can book a flight from Chicago to Azores (average of $469). Flying from Chicago to Azores in November is currently the most expensive (average of $1,030). 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.

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 June 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$550Average$913FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$675Average$1,257FlexibilityNo cancel feeOn-time69%

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