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

Return flights

17 Feb - 24 Feb	Delta
09 Feb - 16 Feb	Delta
05 Feb - 12 Feb	Delta
12 Feb - 17 Feb	Delta
26 Feb - 05 Mar	Delta
19 Feb - 26 Feb	Southwest Airlines
23 Feb - 02 Mar	Southwest Airlines
06 Feb - 13 Feb	Southwest Airlines
07 Feb - 14 Feb	Southwest Airlines
22 Feb - 01 Mar	Southwest Airlines
26 Feb - 01 Mar	Southwest Airlines
20 Feb - 27 Feb	Southwest Airlines
12 Feb - 19 Feb	Delta
16 Feb - 16 Feb	Delta
28 Feb - 07 Mar	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.

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Cheapest return flights from Chicago to St. Thomas in February from 438€

Return flights