Cubs Roster & Staff
Transactions
| Date | Transaction |
| 11/30/21 | RHP Jason Adam elected free agency. |
| 11/30/21 | Chicago Cubs signed free agent RHP Jair Jimenez to a minor league contract. |
| 11/30/21 | Minnesota Twins claimed RHP Trevor Megill off waivers from Chicago Cubs. |
| 11/28/21 | Chicago Cubs signed free agent CF Narciso Crook to a minor league contract. |
| 11/28/21 | Chicago Cubs signed free agent LHP Locke St. John to a minor league contract. |
| 11/22/21 | Cleveland Guardians traded RF Harold Ramirez to Chicago Cubs for cash. |
| 11/19/21 | Chicago Cubs signed free agent RHP Jonathan Holder to a minor league contract. |
| 11/19/21 | Chicago Cubs signed free agent C P.J. Higgins to a minor league contract. |
| 11/19/21 | Chicago Cubs selected the contract of RHP Ethan Roberts from Iowa Cubs. |
| 11/19/21 | Chicago Cubs selected the contract of OF Nelson Velazquez from Tennessee Smokies. |
| 11/12/21 | Chicago Cubs signed free agent RHP Yafrerlyn Vasquez to a minor league contract. |
| 11/12/21 | Chicago Cubs signed free agent RHP Jensi Ramirez to a minor league contract. |
| 11/12/21 | Chicago Cubs signed free agent RHP Eligio Paredes to a minor league contract. |
| 11/12/21 | Chicago Cubs signed free agent LHP Kevin Valdez to a minor league contract. |
| 11/07/21 | Chicago Cubs activated RF Michael Hermosillo from the 60-day injured list. |
| 11/07/21 | Chicago Cubs activated 1B Alfonso Rivas from the 60-day injured list. |
| 11/07/21 | Chicago Cubs activated 2B Nick Madrigal. |
| 11/07/21 | Chicago Cubs activated LHP Brad Wieck from the 60-day injured list. |
| 11/07/21 | Chicago Cubs activated 2B Nick Madrigal. |
| 11/07/21 | Chicago Cubs activated 2B Nick Madrigal. |
| 11/06/21 | Chicago Cubs sent LHP Rex Brothers outright to Iowa Cubs. |
| 11/05/21 | Chicago Cubs claimed LHP Wade Miley off waivers from Cincinnati Reds. |
| 11/05/21 | Chicago Cubs sent RHP Adrian Sampson outright to Iowa Cubs. |
| 11/05/21 | Chicago Cubs sent C P.J. Higgins outright to Iowa Cubs. |
| 11/05/21 | Chicago Cubs activated C P.J. Higgins from the 60-day injured list. |
| 11/05/21 | Chicago Cubs sent 2B Trent Giambrone outright to Iowa Cubs. |
| 11/04/21 | LHP Adam Morgan elected free agency. |
| 11/03/21 | Chicago Cubs sent RHP Jonathan Holder outright to Iowa Cubs. |
| 11/03/21 | Chicago Cubs sent LF Nick Martini outright to Iowa Cubs. |
| 11/03/21 | C Robinson Chirinos elected free agency. |
| 11/03/21 | Chicago Cubs sent RF Trayce Thompson outright to Iowa Cubs. |
| 11/03/21 | Chicago Cubs sent RHP Kohl Stewart outright to Iowa Cubs. |
| 11/03/21 | RHP Zach Davies elected free agency. |
| 11/03/21 | C Jose Lobaton elected free agency. |
| 11/03/21 | 3B Matt Duffy elected free agency. |