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Portimão

$490+ Cheap flights from Chicago (CHI) to Portimão, Portugal

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FAO
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheap flight deals from Chicago to Portimão

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$493
(oojo)

Popular in

March

Cheapest in

February

Average price

$560
Provider with most accurate pricing for Chicago (CHI)-Faro flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Faro flights.
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From Chicago (CHI) to Portimão
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High demand for flights, 7% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($65 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Chicago to Portimão

Cheapest flights from Chicago to Portimão
Explore the most affordable flight options available from Chicago to Portimão. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This oojo deal was found by Cheapflights users on 10/14. 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.
Fri 11/288:15 pmORD - FAO
1 stop32h 10mTAP AIR PORTUGAL
Fri 12/56:05 amFAO - ORD
1 stop15h 20mTAP AIR PORTUGAL
Deal found 10/14$490
This Billigflug deal was found by Cheapflights users on 10/16. 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/308:25 pmORD - FAO
1 stop32h 00mTAP AIR PORTUGAL
Sun 12/76:05 amFAO - ORD
1 stop14h 40mTAP AIR PORTUGAL
Deal found 10/16$499
This KLM deal was found by Cheapflights users on 10/14. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:13 pmORD - FAO
2 stops17h 42mKLM
Fri 12/59:15 amFAO - ORD
1 stop35h 05mKLM
Deal found 10/14$535
This Trip.com deal was found by Cheapflights users on 10/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/294:25 pmORD - FAO
1 stop19h 35mKLM
Sat 12/65:45 pmFAO - ORD
1 stop26h 35mKLM
Deal found 10/15$553
This Trip.com deal was found by Cheapflights users on 10/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/304:25 pmORD - FAO
1 stop20h 00mKLM
Sun 12/76:50 pmFAO - ORD
2 stops28h 56mKLM
Deal found 10/16$562
This KLM deal was found by Cheapflights users on 10/14. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:34 amMDW - FAO
2 stops26h 41mKLM
Sun 12/76:50 pmFAO - MDW
2 stops27h 53mKLM
Deal found 10/14$597
This Mytrip deal was found by Cheapflights users on 10/16. 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.
Sun 11/306:30 pmORD - FAO
2 stops20h 45mMultiple Airlines
Sun 12/76:50 amFAO - ORD
2 stops16h 30mMultiple Airlines
Deal found 10/16$611
This KLM deal was found by Cheapflights users on 10/14. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:34 pmMDW - FAO
2 stops17h 21mKLM
Fri 12/59:15 amFAO - MDW
2 stops20h 34mKLM
Deal found 10/14$645
This Expedia deal was found by Cheapflights users on 10/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:04 pmORD - FAO
2 stops41h 11mBritish Airways
Sat 12/66:55 pmFAO - ORD
2 stops51h 06mBritish Airways
Deal found 10/15$659
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:30 pmORD - FAO
3 stops33h 55mMultiple Airlines
Fri 12/54:35 pmFAO - ORD
3 stops30h 45mMultiple Airlines
Deal found 10/14$722
This Mytrip deal was found by Cheapflights users on 10/15. 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.
Sat 11/296:30 pmORD - FAO
2 stops19h 40mMultiple Airlines
Sat 12/64:35 pmFAO - ORD
3 stops30h 45mMultiple Airlines
Deal found 10/15$727
This lastminute.com deal was found by Cheapflights users on 10/16. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/309:34 amMDW - FAO
2 stops26h 51mKLM
Sun 12/76:50 pmFAO - MDW
2 stops51h 53mKLM
Deal found 10/16$1,123

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Portimão 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 October 16, 2025.
Use the filters below to find and compare flights from Chicago to Portimão that are best for you.

Fly from

Chicago

Fly to

Portimão

Route

Depart

Return

Price

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Fri 11/28

8:15 pm-10:25 am

1 stop32h 10m

Faro

Fri 12/5

6:05 am-3:25 pm

1 stop15h 20m

$490

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Wed 1/14

7:10 pm-3:45 pm

1 stop14h 35m

Faro

Thu 3/12

4:35 pm-4:25 pm

1 stop28h 50m

$494

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Fri 11/28

5:13 pm-4:55 pm

2 stops17h 42m

Faro

Fri 12/5

9:15 am-2:20 pm

1 stop35h 05m

$535

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Sat 11/29

4:25 pm-6:00 pm

1 stop19h 35m

Faro

Sat 12/6

5:45 pm-2:20 pm

1 stop26h 35m

$553

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Wed 12/3

9:34 am-6:15 pm

2 stops26h 41m

Faro

Sun 12/7

6:50 pm-4:43 pm

2 stops27h 53m

$597

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Tue 2/10

4:33 pm-5:30 pm

2 stops18h 57m

Faro

Tue 3/31

3:35 pm-2:26 pm

2 stops28h 51m

$604

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Sat 11/29

6:04 pm-5:15 pm

2 stops41h 11m

Faro

Sat 12/6

6:55 pm-4:01 pm

2 stops51h 06m

$659

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Wed 1/14

5:10 pm-5:30 pm

2 stops18h 20m

Faro

Thu 3/12

7:40 pm-4:25 pm

1 stop25h 45m

$702

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Sun 3/29

6:00 pm-5:20 pm

1 stop17h 20m

Faro

Thu 4/2

6:10 pm-4:00 pm

1 stop27h 50m

$714

ChicagoFaro

ORD - FAO

ORDFAO

Chicago O'Hare Intl

Sat 11/29

6:30 pm-10:25 am

3 stops33h 55m

Faro

Sat 12/6

5:45 pm-5:20 pm

3 stops29h 35m

$748

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 14 results
1
2

Best time to book a flight from Chicago to Portimão

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

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Portimão (average of $411). Flying from Chicago to Portimão in July is currently the most expensive (average of $828). 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.

Reviews of airlines servicing Portimão

Get insights into the airlines that provide service to Portimão. 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 Portimão. Reviews last updated October 16, 2025.
Read reviews from past customers who have flown Aer Lingus and TAP AIR PORTUGAL from Chicago to Portimão. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Aer Lingus
7.2
Good
1,341 reviews

Crew

8.0

Comfort

7.1

Entertainment

6.9

Food

6.5

Overall

7.2

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - DUB

Most airlines board by group even though passengers are seated at the back. At Seatac, passengers were seated starting at the back. Otherwise, flight was good.
Aer Lingus
7.2
Good
1,341 reviews
Aer Lingus
7.2
Good
1,341 reviews

Crew

8.0

Comfort

7.1

Entertainment

6.9

Food

6.5

Overall

7.2

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - DUB

Most airlines board by group even though passengers are seated at the back. At Seatac, passengers were seated starting at the back. Otherwise, flight was good.
TAP AIR PORTUGAL
7.1
Good
2,015 reviews
Aer Lingus
7.2
Good
1,341 reviews

Crew

8.0

Comfort

7.1

Entertainment

6.9

Food

6.5

Overall

7.2

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - DUB

Most airlines board by group even though passengers are seated at the back. At Seatac, passengers were seated starting at the back. Otherwise, flight was good.

Related info for your journey

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

    TAP AIR PORTUGAL and KLM can get you from Chicago to Portimão in just under 17h 42m. Your travel time can differ by up to 14h 28m. Chicago and Portimão are separated by a distance of 4114 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Portimão 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 Portimão?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Portimão (average of $411). Flying from Chicago to Portimão in July is currently the most expensive (average of $828). 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

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Top 3 airlines flying from Chicago to Portimão

Discover the top 3 airlines that operate flights from Chicago to Portimão. 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$486Average$695FlexibilityNo cancel feeOn-timeN/A
Aer LingusCheapest$741Average$1,087FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$757Average$828FlexibilityNo cancel feeOn-time69%

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