AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU)
in August 2025 (see full year ).
Return flights
02 Aug
- 16 Aug
Frontier Airlines
$ 238
02 Aug
- 09 Aug
Frontier Airlines
$ 240
03 Aug
- 08 Aug
Spirit Airlines
$ 241
direct
16 Aug
- 24 Aug
Frontier Airlines
$ 242
20 Aug
- 23 Aug
Spirit Airlines
$ 242
direct
09 Aug
- 13 Aug
Spirit Airlines
$ 242
direct
17 Aug
- 27 Aug
Spirit Airlines
$ 242
direct
23 Aug
- 27 Aug
Spirit Airlines
$ 242
direct
16 Aug
- 23 Aug
Spirit Airlines
$ 242
direct
16 Aug
- 21 Aug
Frontier Airlines
$ 243
29 Aug
- 04 Sep
Frontier Airlines
$ 248
29 Aug
- 05 Sep
Frontier Airlines
$ 248
28 Aug
- 03 Sep
Frontier Airlines
$ 259
26 Aug
- 03 Sep
Spirit Airlines
$ 297
direct
28 Aug
- 01 Sep
Frontier Airlines
$ 300
27 Aug
- 01 Sep
Spirit Airlines
$ 316
27 Aug
- 03 Sep
Spirit Airlines
$ 317
direct
29 Aug
- 02 Sep
Frontier Airlines
$ 372
28 Aug
- 02 Sep
Frontier Airlines
$ 390
29 Aug
- 04 Sep
United
$ 499
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.
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