| BIG3 | 08/24 18:00 | 1 | [1] Chicago Triplets v Miami 305 [3] | L | 48-52 | |
| BIG3 | 08/17 20:00 | 2 | [4] LA Riot v Chicago Triplets [1] | W | 38-50 | |
| BIG3 | 08/09 23:00 | 8 | [2] Chicago Triplets v Detroit Amps [4] | W | 50-42 | |
| BIG3 | 08/02 20:00 | 7 | [1] Miami 305 v Chicago Triplets [3] | W | 41-50 | |
| BIG3 | 07/26 20:45 | 6 | [4] Boston Ball Hogs v Chicago Triplets [5] | W | 43-51 | |
| BIG3 | 07/20 19:00 | 5 | [5] LA Riot v Chicago Triplets [2] | L | 50-30 | |
| BIG3 | 07/13 19:00 | 4 | [2] Chicago Triplets v Dallas Power [2] | W | 50-45 | |
| BIG3 | 06/29 20:45 | 3 | [4] Chicago Triplets v DMV Trilogy [8] | W | 51-48 | |
| BIG3 | 06/22 19:00 | 2 | [2] Houston Rig Hands v Chicago Triplets [5] | W | 34-51 | |
| BIG3 | 06/14 21:00 | 1 | [2] Detroit Amps v Chicago Triplets [2] | L | 50-48 | |
| BIG3 | 08/04 21:00 | 8 | [4] Triplets v Bivouac [2] | L | 46-51 | |
| BIG3 | 07/28 19:00 | 7 | [6] Ball Hogs v Triplets [5] | W | 42-51 |
The Chicago Triplets are an American men's 3-on-3 basketball team based in Chicago, Illinois that plays in the BIG3. They were the first team announced in the 2019 BIG3 expansion.
Originally without a home city for their first five seasons, the Triplets were announced to be based in Chicago when the league switched to a city-based model for the 2025 season.
At the end of the 2019 BIG3 season, the Triplets won the championship over Killer 3's.