Cheapest return flights from Chicago to San Juan in January from 174€

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in January 2026 (see full year).

Return flights

26 Jan - 29 Jan Frontier Airlines
30 Jan - 04 Feb Frontier Airlines
27 Jan - 11 Feb Frontier Airlines
21 Jan - 30 Jan Southwest Airlines
26 Jan - 28 Jan Southwest Airlines
22 Jan - 27 Jan Southwest Airlines
21 Jan - 27 Jan Southwest Airlines
24 Jan - 29 Jan Delta
27 Jan - 30 Jan Delta
23 Jan - 27 Jan Southwest Airlines
20 Jan - 27 Jan Southwest Airlines
25 Jan - 27 Jan Southwest Airlines
30 Jan - 01 Feb Frontier Airlines
30 Jan - 03 Feb Frontier Airlines
29 Jan - 03 Feb Frontier Airlines
29 Jan - 04 Feb Southwest Airlines
15 Jan - 02 Feb Frontier Airlines
28 Jan - 01 Feb Frontier Airlines
29 Jan - 01 Feb Frontier Airlines
27 Jan - 01 Feb Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan in January.

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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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