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

Return flights

26 Jan - 05 Feb	Delta
27 Jan - 05 Feb	Delta
19 Jan - 26 Jan	Delta
08 Jan - 15 Jan	Delta
29 Jan - 05 Feb	Delta
08 Jan - 12 Jan	Delta
23 Jan - 26 Jan	Delta
14 Jan - 21 Jan	Delta
28 Jan - 05 Feb	Delta
04 Jan - 09 Jan	Delta
18 Jan - 25 Jan	Delta
22 Jan - 29 Jan	Delta
24 Jan - 27 Jan	Delta
25 Jan - 01 Feb	Delta
30 Jan - 06 Feb	Delta
31 Jan - 07 Feb	Delta
05 Jan - 09 Jan	Delta
30 Jan - 02 Feb	Delta

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

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 January from 438€

Return flights