Cheapest return flights from Chicago to San Juan in January from 132€
AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU)
in January 2026 (see full year ).
Return flights
07 Jan
- 15 Jan
Frontier Airlines
132 €
07 Jan
- 14 Jan
Frontier Airlines
145 €
09 Jan
- 12 Jan
Frontier Airlines
182 €
07 Jan
- 12 Jan
Frontier Airlines
195 €
31 Jan
- 07 Feb
Frontier Airlines
195 €
22 Jan
- 29 Jan
Frontier Airlines
213 €
07 Jan
- 10 Jan
Frontier Airlines
226 €
08 Jan
- 15 Jan
Frontier Airlines
226 €
23 Jan
- 27 Jan
Southwest Airlines
233 €
03 Jan
- 10 Jan
Frontier Airlines
259 €
05 Jan
- 08 Jan
Frontier Airlines
280 €
31 Jan
- 01 Feb
Southwest Airlines
319 €
31 Jan
- 08 Feb
Southwest Airlines
324 €
30 Jan
- 01 Feb
Frontier Airlines
368 €
Also check the deals for one-way flights from Chicago to San Juan in January .
Powered by
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.
Find us on social media
Feel free to contact us with any feedback or request another flight research.
Find us on social media