Cheapest return flights from Chicago to San Juan in February from 161€

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in February 2025 (see full year).

Return flights

27 Feb - 03 Mar Frontier Airlines
21 Feb - 24 Feb Frontier Airlines
21 Feb - 25 Feb Frontier Airlines
28 Feb - 03 Mar Frontier Airlines
27 Feb - 02 Mar Frontier Airlines
21 Feb - 01 Mar Frontier Airlines
05 Feb - 12 Feb Southwest Airlines
09 Feb - 12 Feb Frontier Airlines
10 Feb - 17 Feb Frontier Airlines
01 Feb - 04 Feb Southwest Airlines
05 Feb - 11 Feb Southwest Airlines
05 Feb - 09 Feb Southwest Airlines
19 Feb - 24 Feb Southwest Airlines
12 Feb - 18 Feb Frontier Airlines

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

Skyscanner

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 San Juan

Cheap car rent in San Juan