Chicago to Sal flights in May 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 · May 2027 · One adult in economy

Travel dates	Airline	Stops	Total (USD)
May 1, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 1, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 1, 2027 – May 4, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 1, 2027 – May 4, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 1, 2027 – May 8, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 1, 2027 – May 8, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 2, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 2, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 2, 2027 – May 5, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 2, 2027 – May 5, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 2, 2027 – May 9, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 2, 2027 – May 9, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 3, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 3, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 3, 2027 – May 6, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 3, 2027 – May 6, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 3, 2027 – May 10, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 3, 2027 – May 10, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 4, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 4, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 4, 2027 – May 7, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 4, 2027 – May 7, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 4, 2027 – May 11, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 4, 2027 – May 11, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 5, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 5, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 5, 2027 – May 8, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 5, 2027 – May 8, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 5, 2027 – May 12, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 5, 2027 – May 12, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 6, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 6, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 6, 2027 – May 9, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 6, 2027 – May 9, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 6, 2027 – May 13, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 6, 2027 – May 13, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 7, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 7, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 7, 2027 – May 10, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 7, 2027 – May 10, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 7, 2027 – May 14, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 7, 2027 – May 14, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 8, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 8, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 8, 2027 – May 11, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 8, 2027 – May 11, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 8, 2027 – May 15, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 8, 2027 – May 15, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 9, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 9, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 9, 2027 – May 12, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 9, 2027 – May 12, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 9, 2027 – May 16, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 9, 2027 – May 16, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 10, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 10, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 10, 2027 – May 13, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 10, 2027 – May 13, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 10, 2027 – May 17, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 10, 2027 – May 17, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 11, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 11, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 11, 2027 – May 14, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 11, 2027 – May 14, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 11, 2027 – May 18, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 11, 2027 – May 18, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 12, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 12, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 12, 2027 – May 15, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 12, 2027 – May 15, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 12, 2027 – May 19, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 12, 2027 – May 19, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 13, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 13, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 13, 2027 – May 16, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 13, 2027 – May 16, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 13, 2027 – May 20, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 13, 2027 – May 20, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 14, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 14, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 14, 2027 – May 17, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 14, 2027 – May 17, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 14, 2027 – May 21, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 14, 2027 – May 21, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 15, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 15, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 15, 2027 – May 18, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 15, 2027 – May 18, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 15, 2027 – May 22, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 15, 2027 – May 22, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 16, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 16, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 16, 2027 – May 19, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 16, 2027 – May 19, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 16, 2027 – May 23, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 16, 2027 – May 23, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 17, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 17, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 17, 2027 – May 20, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 17, 2027 – May 20, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 17, 2027 – May 24, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 17, 2027 – May 24, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 18, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 18, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 18, 2027 – May 21, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 18, 2027 – May 21, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 18, 2027 – May 25, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 18, 2027 – May 25, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 19, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 19, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 19, 2027 – May 22, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 19, 2027 – May 22, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 19, 2027 – May 26, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 19, 2027 – May 26, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 20, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 20, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 20, 2027 – May 23, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 20, 2027 – May 23, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 20, 2027 – May 27, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 20, 2027 – May 27, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 21, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 21, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 21, 2027 – May 24, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 21, 2027 – May 24, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 21, 2027 – May 28, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 21, 2027 – May 28, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 22, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 22, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 22, 2027 – May 25, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 22, 2027 – May 25, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 22, 2027 – May 29, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 22, 2027 – May 29, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 23, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 23, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 23, 2027 – May 26, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 23, 2027 – May 26, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 23, 2027 – May 30, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 23, 2027 – May 30, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 24, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 24, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 24, 2027 – May 27, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 24, 2027 – May 27, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 24, 2027 – May 31, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 24, 2027 – May 31, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 25, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 25, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 25, 2027 – May 28, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 25, 2027 – May 28, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 25, 2027 – Jun 1, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 25, 2027 – Jun 1, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 26, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 26, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 26, 2027 – May 29, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 26, 2027 – May 29, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 26, 2027 – Jun 2, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 26, 2027 – Jun 2, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 27, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 27, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 27, 2027 – May 30, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 27, 2027 – May 30, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 27, 2027 – Jun 3, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 27, 2027 – Jun 3, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 28, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 28, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 28, 2027 – May 31, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1306.25
May 28, 2027 – May 31, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1330.00
May 28, 2027 – Jun 4, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 28, 2027 – Jun 4, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 29, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 29, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 29, 2027 – Jun 1, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 29, 2027 – Jun 1, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 29, 2027 – Jun 5, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 29, 2027 – Jun 5, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 30, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 30, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 30, 2027 – Jun 2, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 30, 2027 – Jun 2, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 30, 2027 – Jun 6, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 30, 2027 – Jun 6, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 31, 2027 · One way	United Airlines	Up to 2 stops each way	$902.50
May 31, 2027 · One way	Swiss International Air Lines	Up to 2 stops each way	$926.25
May 31, 2027 – Jun 3, 2027 · 3 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 31, 2027 – Jun 3, 2027 · 3 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50
May 31, 2027 – Jun 7, 2027 · 7 nights	United Airlines / TAP Air Portugal	Up to 2 stops each way	$1338.75
May 31, 2027 – Jun 7, 2027 · 7 nights	Swiss International Air Lines / TAP Air Portugal	Up to 2 stops each way	$1362.50

Each fare is an example for the dates and airports listed. Check its live price before booking.

Choose May 2027 dates and check live prices

All months for Chicago to Sal

Hotels near SID

Melia Dunas Beach Resort & Spa - All Inclusive (Santa Maria) · Sol Dunas - All Inclusive (São Paulo, Sal) · Hotel Da Luz (Santa Maria) · Hotel Riu Palace Santa Maria - All Inclusive (Santa Maria) · Hotel Aquamarina Suites THe Senses Collection (Santa Maria)

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