AirHint found the following cheapest return flights from Chicago (MDW) to St. Thomas (STT) in February 2026 (see full year).

Return flights

05 Feb - 08 Feb	Frontier Airlines
18 Feb - 26 Feb	Southwest Airlines
20 Feb - 25 Feb	Delta
28 Feb - 04 Mar	Delta
05 Feb - 09 Feb	Delta
28 Feb - 06 Mar	Southwest Airlines
14 Feb - 17 Feb	Delta
28 Feb - 07 Mar	Southwest Airlines
13 Feb - 16 Feb	Frontier Airlines
25 Feb - 01 Mar	Southwest Airlines
14 Feb - 16 Feb	Frontier Airlines
26 Feb - 01 Mar	Southwest Airlines
25 Feb - 28 Feb	Southwest Airlines
26 Feb - 28 Feb	Southwest Airlines

Also check the deals for one-way flights from Chicago to St. Thomas in February.

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 St. Thomas

Cheap car rent in St. Thomas

Cheapest return flights from Chicago to St. Thomas in February from $462

Return flights