Cheapest return flights from Chicago (MDW) to San Juan (SJU), January

14 dates in January 2027, from $ 270. Book in one tap, or check whether to buy now or wait.

One-wayReturn
Dates, airline, and price
Dates Airline Price
18 Jan 28 Jan 2027 Frontier Airlines
30 Jan 3 Feb 2027 Southwest Airlines
23 Jan 28 Jan 2027 Southwest Airlines
23 Jan 29 Jan 2027 Southwest Airlines
23 Jan 30 Jan 2027 Southwest Airlines
12 Jan 15 Jan 2027 Frontier Airlines
12 Jan 22 Jan 2027 Frontier Airlines
19 Jan 29 Jan 2027 Southwest Airlines
18 Jan 29 Jan 2027 Southwest Airlines
25 Jan 5 Feb 2027 Southwest Airlines
23 Jan 27 Jan 2027 Southwest Airlines
12 Jan 29 Jan 2027 Frontier Airlines
26 Jan 7 Feb 2027 Southwest Airlines
4 Jan 12 Feb 2027 Southwest Airlines
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Deals for one-way flights from Chicago to San Juan in January.

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About these fares

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