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$914+ Cheap flights from Midway (MDW) to São Miguel

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDL
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to São Miguel

Keep the following information in mind while searching for Midway to São Miguel flight deals. Data was last updated August 14, 2025.

Round-trip from

$914
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$963
From Chicago Midway to São Miguel
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($193 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Midway to São Miguel

Cheapest flights from Midway to São Miguel
Explore the most affordable flight options available from Midway to São Miguel. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/139:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Tue 9/235:30 pmPDL - MDW
2 stops27h 28mMultiple Airlines
Deal found 8/13$914
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 10/179:35 amMDW - PDL
2 stops19h 10mMultiple Airlines
Thu 10/234:55 pmPDL - MDW
1 stop20h 44mMultiple Airlines
Deal found 8/12$920
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/139:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Mon 9/226:15 pmPDL - MDW
2 stops27h 09mMultiple Airlines
Deal found 8/13$930
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 9/189:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Tue 9/235:30 pmPDL - MDW
2 stops27h 28mMultiple Airlines
Deal found 8/13$935
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/199:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Tue 9/235:30 pmPDL - MDW
2 stops27h 28mMultiple Airlines
Deal found 8/13$939
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 9/189:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Mon 9/226:15 pmPDL - MDW
2 stops27h 09mMultiple Airlines
Deal found 8/13$952
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/199:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Mon 9/226:15 pmPDL - MDW
2 stops27h 09mMultiple Airlines
Deal found 8/13$956
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Thu 9/259:35 amMDW - PDL
2 stops16h 15mMultiple Airlines
Tue 10/77:30 pmPDL - MDW
3 stops25h 54mMultiple Airlines
Deal found 8/14$1,272
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/199:35 amMDW - PDL
1 stop16h 05mMultiple Airlines
Fri 9/2610:45 amPDL - MDW
2 stops26h 54mMultiple Airlines
Deal found 8/13$1,274
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 12/2611:00 amMDW - PDL
1 stop14h 50mMultiple Airlines
Fri 1/24:50 pmPDL - MDW
1 stop22h 15mMultiple Airlines
Deal found 8/12$1,424

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to São Miguel 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to São Miguel that are best for you.

Fly from

Midway

Fly to

São Miguel

Route

Depart

Return

Price

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Sat 9/13

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Tue 9/23

5:30 pm-3:58 pm

2 stops27h 28m

$914

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Fri 10/17

9:35 am-9:45 am

2 stops19h 10m

Ponta Delgada Nordela

Thu 10/23

4:55 pm-8:39 am

1 stop20h 44m

$920

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Sat 9/13

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Mon 9/22

6:15 pm-4:24 pm

2 stops27h 09m

$930

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Thu 9/18

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Tue 9/23

5:30 pm-3:58 pm

2 stops27h 28m

$935

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Fri 9/19

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Tue 9/23

5:30 pm-3:58 pm

2 stops27h 28m

$939

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Thu 9/18

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Mon 9/22

6:15 pm-4:24 pm

2 stops27h 09m

$952

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Fri 9/19

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Mon 9/22

6:15 pm-4:24 pm

2 stops27h 09m

$956

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Thu 9/25

9:35 am-6:50 am

2 stops16h 15m

Ponta Delgada Nordela

Tue 10/7

7:30 pm-4:24 pm

3 stops25h 54m

$1,272

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Fri 9/19

9:35 am-6:40 am

1 stop16h 05m

Ponta Delgada Nordela

Fri 9/26

10:45 am-8:39 am

2 stops26h 54m

$1,274

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Wed 9/24

6:15 pm-4:05 pm

2 stops16h 50m

$6,164

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 14 results
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Best time to book a flight from Midway to São Miguel

Have a flexible travel schedule? Discover the best time to fly to São Miguel 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 São Miguel
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 São Miguel. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

  • How can I find direct flights from Midway to São Miguel?

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

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

    Yes. Cheapflights offers flight deals from Midway to São Miguel 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 São Miguel?

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

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