Cheapest return flights from Chicago to San Juan in January from $116
AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU)
in January 2026 (see full year ).
Return flights
10 Jan
- 15 Jan
Frontier Airlines
$ 116
07 Jan
- 15 Jan
Frontier Airlines
$ 116
12 Jan
- 15 Jan
Frontier Airlines
$ 116
26 Jan
- 29 Jan
Frontier Airlines
$ 116
08 Jan
- 15 Jan
Frontier Airlines
$ 116
26 Jan
- 05 Feb
Frontier Airlines
$ 116
07 Jan
- 13 Jan
Frontier Airlines
$ 117
07 Jan
- 12 Jan
Frontier Airlines
$ 143
24 Jan
- 31 Jan
Frontier Airlines
$ 147
08 Jan
- 12 Jan
Frontier Airlines
$ 147
05 Jan
- 14 Jan
Frontier Airlines
$ 148
20 Jan
- 04 Feb
jetBlue
$ 178
30 Jan
- 07 Feb
jetBlue
$ 181
20 Jan
- 04 Feb
Spirit Airlines
$ 187
direct
31 Jan
- 03 Feb
Spirit Airlines
$ 187
direct
26 Jan
- 05 Feb
Spirit Airlines
$ 188
direct
26 Jan
- 10 Feb
Spirit Airlines
$ 188
direct
26 Jan
- 04 Feb
Spirit Airlines
$ 188
direct
26 Jan
- 07 Feb
Spirit Airlines
$ 188
direct
26 Jan
- 03 Feb
Spirit Airlines
$ 188
direct
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