AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU)
in August 2025 (see full year ).
Return flights
13 Aug
- 23 Aug
Spirit Airlines
$ 232
direct
12 Aug
- 15 Aug
Spirit Airlines
$ 251
12 Aug
- 21 Aug
Spirit Airlines
$ 262
08 Aug
- 11 Aug
Spirit Airlines
$ 263
10 Aug
- 14 Aug
Spirit Airlines
$ 273
10 Aug
- 15 Aug
Spirit Airlines
$ 274
16 Aug
- 20 Aug
Spirit Airlines
$ 277
21 Aug
- 26 Aug
Spirit Airlines
$ 278
direct
12 Aug
- 19 Aug
Spirit Airlines
$ 278
26 Aug
- 01 Sep
Spirit Airlines
$ 280
24 Aug
- 31 Aug
Spirit Airlines
$ 283
28 Aug
- 03 Sep
Frontier Airlines
$ 308
28 Aug
- 01 Sep
Frontier Airlines
$ 308
26 Aug
- 02 Sep
Spirit Airlines
$ 327
direct
27 Aug
- 01 Sep
Spirit Airlines
$ 331
27 Aug
- 02 Sep
Spirit Airlines
$ 374
28 Aug
- 03 Sep
Spirit Airlines
$ 382
direct
28 Aug
- 02 Sep
Spirit Airlines
$ 422
direct
27 Aug
- 02 Sep
United
$ 505
direct
26 Aug
- 01 Sep
United
$ 561
direct
Also check the deals for one-way flights from Chicago to San Juan in August .
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.