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$811+ Cheap flights from Midway (MDW) 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — FAO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to Portimão

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

Round-trip from

$811
(KLM)

Popular in

March

Cheapest in

February

Average price

$788
From Chicago Midway to Portimão
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High demand for flights, 5% potential price rise
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Cheapest flight prices on average. 7% potential price decrease ($66 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 Midway to Portimão

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

This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:23 pmMDW - FAO
2 stops18h 47mKLM
Tue 11/47:45 pmFAO - MDW
2 stops26h 30mKLM
Deal found 9/15$811
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:47 pmMDW - FAO
2 stops36h 48mKLM
Sat 11/228:10 pmFAO - MDW
2 stops26h 28mKLM
Deal found 9/14$962
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:23 pmMDW - FAO
2 stops33h 12mKLM
Thu 11/67:05 pmFAO - MDW
2 stops27h 09mKLM
Deal found 9/15$1,101
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:15 pmMDW - FAO
2 stops18h 50mKLM
Thu 10/28:20 pmFAO - MDW
2 stops28h 15mKLM
Deal found 9/16$1,211
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:25 pmMDW - FAO
2 stops19h 35mKLM
Thu 1/87:05 pmFAO - MDW
2 stops27h 20mKLM
Deal found 9/14$1,651
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.
Mon 9/299:35 amMDW - FAO
3 stops20h 50mMultiple Airlines
Thu 10/26:05 amFAO - MDW
3 stops32h 34mMultiple Airlines
Deal found 9/16$1,751
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:25 pmMDW - FAO
2 stops19h 35mKLM
Tue 1/67:45 pmFAO - MDW
2 stops26h 40mKLM
Deal found 9/14$1,887
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:00 pmMDW - FAO
2 stops17h 55mKLM
Thu 1/87:05 pmFAO - MDW
2 stops27h 20mKLM
Deal found 9/14$2,029
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:00 pmMDW - FAO
2 stops17h 55mKLM
Tue 1/67:45 pmFAO - MDW
2 stops26h 40mKLM
Deal found 9/14$2,265
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:04 pmMDW - FAO
2 stops20h 01mKLM
Wed 10/158:00 pmFAO - MDW
2 stops28h 25mKLM
Deal found 9/14$5,355

Cheapflights Fare Finder

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

Fly from

Midway

Fly to

Portimão

Route

Depart

Return

Price

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Sun 10/19

6:23 pm-7:10 pm

2 stops18h 47m

Faro

Tue 11/4

7:45 pm-4:15 pm

2 stops26h 30m

$811

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Thu 11/13

1:47 pm-8:35 am

2 stops36h 48m

Faro

Sat 11/22

8:10 pm-4:38 pm

2 stops26h 28m

$962

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Thu 10/30

6:23 pm-8:35 am

2 stops33h 12m

Faro

Thu 11/6

7:05 pm-4:14 pm

2 stops27h 09m

$1,101

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Mon 9/29

6:15 pm-7:05 pm

2 stops18h 50m

Faro

Thu 10/2

8:20 pm-6:35 pm

2 stops28h 15m

$1,211

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Mon 9/29

9:35 am-12:25 pm

3 stops20h 50m

Faro

Thu 10/2

6:05 am-8:39 am

3 stops32h 34m

$1,751

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Mon 10/6

6:23 pm-7:05 pm

2 stops18h 42m

Faro

Wed 10/15

8:00 pm-6:25 pm

2 stops28h 25m

$7,063

ChicagoFaro

MDW - FAO

MDWFAO

Chicago Midway

Wed 9/24

5:20 pm-11:20 am

3 stops36h 00m

$1,767

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from Midway to Portimão

Have a flexible travel schedule? Discover the best time to fly to Portimão from Midway 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 Midway Airport to Portimão
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway Airport to Portimão?

    Airlines like KLM fly from Chicago Midway Airport to Portimão in about 18h 47m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 4112 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Portimão?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portimão (average of $628). Flying from Chicago Midway Airport to Portimão in June is currently the most expensive (average of $1,329). 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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