AirHint found the following cheapest return flights from Boston (BOS) to Praia, Santiago Island (RAI) in October 2025 (see full year).

Return flights

29 Oct - 05 Nov	TAP
01 Oct - 05 Nov	Azores Airlines
01 Oct - 15 Oct	Azores Airlines
08 Oct - 21 Oct	Azores Airlines
01 Oct - 21 Oct	Azores Airlines
25 Oct - 08 Nov	TAP
01 Oct - 24 Oct	Azores Airlines
01 Oct - 20 Oct	Azores Airlines
01 Oct - 14 Oct	Azores Airlines
02 Oct - 13 Oct	TAP
01 Oct - 13 Oct	Azores Airlines
03 Oct - 06 Oct	TAP
01 Oct - 04 Oct	Azores Airlines

Also check the deals for one-way flights from Boston to Praia, Santiago Island in October.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Praia, Santiago Island

Cheap car rent in Praia, Santiago Island

Cheapest return flights from Boston to Praia, Santiago Island in October from 545€

Return flights