Chicago to Sal flights in September 2027

Saved fares include round trips from $1,306 and one-way flights from $903 for one adult in economy. Fare observations: October 29, 2026.

Departure airports: Chicago (ORD,MDW). Destination: Sal (SID).

ORD → SID · September 2027 · One adult in economy

Travel dates Airline Stops Total (USD)
Sep 1, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 1, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 1, 2027 – Sep 4, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 1, 2027 – Sep 4, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 1, 2027 – Sep 8, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 1, 2027 – Sep 8, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 2, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 2, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 2, 2027 – Sep 5, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 2, 2027 – Sep 5, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 2, 2027 – Sep 9, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 2, 2027 – Sep 9, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 3, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 3, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 3, 2027 – Sep 6, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 3, 2027 – Sep 6, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 3, 2027 – Sep 10, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 3, 2027 – Sep 10, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 4, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 4, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 4, 2027 – Sep 7, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 4, 2027 – Sep 7, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 4, 2027 – Sep 11, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 4, 2027 – Sep 11, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 5, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 5, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 5, 2027 – Sep 8, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 5, 2027 – Sep 8, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 5, 2027 – Sep 12, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 5, 2027 – Sep 12, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 6, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 6, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 6, 2027 – Sep 9, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 6, 2027 – Sep 9, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 6, 2027 – Sep 13, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 6, 2027 – Sep 13, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 7, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 7, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 7, 2027 – Sep 10, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 7, 2027 – Sep 10, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 7, 2027 – Sep 14, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 7, 2027 – Sep 14, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 8, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 8, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 8, 2027 – Sep 11, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 8, 2027 – Sep 11, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 8, 2027 – Sep 15, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 8, 2027 – Sep 15, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 9, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 9, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 9, 2027 – Sep 12, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 9, 2027 – Sep 12, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 9, 2027 – Sep 16, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 9, 2027 – Sep 16, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 10, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 10, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 10, 2027 – Sep 13, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 10, 2027 – Sep 13, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 10, 2027 – Sep 17, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 10, 2027 – Sep 17, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 11, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 11, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 11, 2027 – Sep 14, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 11, 2027 – Sep 14, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 11, 2027 – Sep 18, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 11, 2027 – Sep 18, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 12, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 12, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 12, 2027 – Sep 15, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 12, 2027 – Sep 15, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 12, 2027 – Sep 19, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 12, 2027 – Sep 19, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 13, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 13, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 13, 2027 – Sep 16, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 13, 2027 – Sep 16, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 13, 2027 – Sep 20, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 13, 2027 – Sep 20, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 14, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 14, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 14, 2027 – Sep 17, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 14, 2027 – Sep 17, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 14, 2027 – Sep 21, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 14, 2027 – Sep 21, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 15, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 15, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 15, 2027 – Sep 18, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 15, 2027 – Sep 18, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 15, 2027 – Sep 22, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 15, 2027 – Sep 22, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 16, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 16, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 16, 2027 – Sep 19, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 16, 2027 – Sep 19, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 16, 2027 – Sep 23, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 16, 2027 – Sep 23, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 17, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 17, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 17, 2027 – Sep 20, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 17, 2027 – Sep 20, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 17, 2027 – Sep 24, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 17, 2027 – Sep 24, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 18, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 18, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 18, 2027 – Sep 21, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 18, 2027 – Sep 21, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 18, 2027 – Sep 25, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 18, 2027 – Sep 25, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 19, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 19, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 19, 2027 – Sep 22, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 19, 2027 – Sep 22, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 19, 2027 – Sep 26, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 19, 2027 – Sep 26, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 20, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 20, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 20, 2027 – Sep 23, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 20, 2027 – Sep 23, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 20, 2027 – Sep 27, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 20, 2027 – Sep 27, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 21, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 21, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 21, 2027 – Sep 24, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 21, 2027 – Sep 24, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 21, 2027 – Sep 28, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 21, 2027 – Sep 28, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 22, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 22, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 22, 2027 – Sep 25, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 22, 2027 – Sep 25, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 22, 2027 – Sep 29, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 22, 2027 – Sep 29, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 23, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 23, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 23, 2027 – Sep 26, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 23, 2027 – Sep 26, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 23, 2027 – Sep 30, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 23, 2027 – Sep 30, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 24, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 24, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 24, 2027 – Sep 27, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 24, 2027 – Sep 27, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 24, 2027 – Oct 1, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 24, 2027 – Oct 1, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 25, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 25, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 25, 2027 – Sep 28, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 25, 2027 – Sep 28, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 25, 2027 – Oct 2, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 25, 2027 – Oct 2, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 26, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 26, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 26, 2027 – Sep 29, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 26, 2027 – Sep 29, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 26, 2027 – Oct 3, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 26, 2027 – Oct 3, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 27, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 27, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 27, 2027 – Sep 30, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1306.25
Sep 27, 2027 – Sep 30, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1330.00
Sep 27, 2027 – Oct 4, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 27, 2027 – Oct 4, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 28, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 28, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 28, 2027 – Oct 1, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 28, 2027 – Oct 1, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 28, 2027 – Oct 5, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 28, 2027 – Oct 5, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 29, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 29, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 29, 2027 – Oct 2, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 29, 2027 – Oct 2, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 29, 2027 – Oct 6, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 29, 2027 – Oct 6, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 30, 2027 · One way United Airlines Up to 2 stops each way $902.50
Sep 30, 2027 · One way Swiss International Air Lines Up to 2 stops each way $926.25
Sep 30, 2027 – Oct 3, 2027 · 3 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 30, 2027 – Oct 3, 2027 · 3 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50
Sep 30, 2027 – Oct 7, 2027 · 7 nights United Airlines / TAP Air Portugal Up to 2 stops each way $1338.75
Sep 30, 2027 – Oct 7, 2027 · 7 nights Swiss International Air Lines / TAP Air Portugal Up to 2 stops each way $1362.50

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