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$1,077+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDL
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$980
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$886
Provider with most accurate pricing for Chicago (CHI)-Ponta Delgada Nordela flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Ponta Delgada Nordela flights.
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From Chicago Midway to São Miguel
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Highest demand for flights based on searches. 13% potential increase in price ($150 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($52 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 20, 2025.

This Mytrip deal was found by Cheapflights users on 11/20. 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 12/2811:00 amMDW - PDL
1 stop14h 50mMultiple Airlines
Fri 1/25:50 pmPDL - MDW
2 stops26h 30mMultiple Airlines
Deal found 11/20$2,024

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 November 20, 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

Sun 1/4

4:15 pm-6:25 am

2 stops33h 10m

Ponta Delgada Nordela

Sun 1/11

4:50 pm-1:09 pm

2 stops25h 19m

$1,077

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Sat 1/3

11:05 am-6:25 am

2 stops14h 20m

Ponta Delgada Nordela

Sat 1/10

5:40 pm-3:20 pm

2 stops26h 40m

$1,139

ChicagoPonta Delgada

MDW - PDL

MDWPDL

Chicago Midway

Sun 12/28

11:00 am-6:50 am

1 stop14h 50m

Ponta Delgada Nordela

Fri 1/2

5:50 pm-3:20 pm

2 stops26h 30m

$2,024

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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.

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Alternative routes for Midway to São Miguel

See prices for flight routes from nearby airports that may be better suited for you.
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