Cheap flights from Chicago to São Miguel Island

View AU$1,047 flight on Thu, 5 Feb. 2026Opens in a new window

Popular airlines from Chicago to São Miguel Island

  • TAP Portugal

    TAP Portugal

  • United

    United

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago (CHI) to São Miguel Island (PDL)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Thu, 14 Aug. - Thu, 28 Aug.
ORD
Chicago
PDL
São Miguel Island
AU$1,279 Return, found 12 hours ago
AU$1,279
Return
found 12 hours ago
Select TAP Portugal flight, departing Thu, 14 Aug. from Chicago to São Miguel Island, returning Thu, 28 Aug., priced at AU$1,279 found 12 hours ago
TAP Portugal
Thu, 14 Aug. - Thu, 28 Aug.
ORD
Chicago
PDL
São Miguel Island
AU$1,417 Return, found 12 hours ago
AU$1,417
Return
found 12 hours ago
Select TAP Portugal flight, departing Thu, 14 Aug. from Chicago to São Miguel Island, returning Thu, 28 Aug., priced at AU$1,417 found 12 hours ago
TAP Portugal
Thu, 5 Feb. - Thu, 19 Feb.
ORD
Chicago
PDL
São Miguel Island
AU$1,447 Return, found 12 hours ago
AU$1,447
Return
found 12 hours ago
Select TAP Portugal flight, departing Thu, 5 Feb. from Chicago to São Miguel Island, returning Thu, 19 Feb., priced at AU$1,447 found 12 hours ago
United
Thu, 5 Feb. - Thu, 19 Feb.
ORD
Chicago
PDL
São Miguel Island
AU$1,545 Return, found 12 hours ago
AU$1,545
Return
found 12 hours ago
Select United flight, departing Thu, 5 Feb. from Chicago to São Miguel Island, returning Thu, 19 Feb., priced at AU$1,545 found 12 hours ago
American Airlines
Thu, 5 Feb. - Thu, 19 Feb.
ORD
Chicago
PDL
São Miguel Island
AU$1,632 Return, found 12 hours ago
AU$1,632
Return
found 12 hours ago
Select American Airlines flight, departing Thu, 5 Feb. from Chicago to São Miguel Island, returning Thu, 19 Feb., priced at AU$1,632 found 12 hours ago
Turkish Airlines
Thu, 14 Aug. - Thu, 28 Aug.
ORD
Chicago
PDL
São Miguel Island
AU$2,731 Return, found 12 hours ago
AU$2,731
Return
found 12 hours ago
Select Turkish Airlines flight, departing Thu, 14 Aug. from Chicago to São Miguel Island, returning Thu, 28 Aug., priced at AU$2,731 found 12 hours ago
*Available to Expedia members.