On May 21, 2021, at about 1230 central daylight time, two Southwest B737’s collided while taxiing near the gate area at Chicago Midway International Airport (MDW), Chicago, Illinois. There were no injuries to the passengers and crew onboard either airplane. One airplane was substantially damaged and the other received minor damage. According to the operator, after landing, N289CT taxied to the assigned gate B-15 and was awaiting the ground marshalling crew. The flight crew of N289CT reported that they positioned the airplane on the J-line leading to the gate parking spot and set the brake while awaiting the ground crew. The marshallers arrived and began to signal the crew into the gate. Shortly after releasing the parking brake, the flight crew reported feeling the airplane shudder. The captain looked out the left window and noticed the N8686A taxiing behind with damage to its right winglet. N289CT then proceeded to the gate and deplaned with no further incident. Post accident inspection of the airplane revealed substantial damage to both elevators. N8686A was cleared to taxi from gate B14 to runway 22L via taxiways T and Y. While taxiing NE on taxiway Y, the aircraft's right winglet struck the aft portion of N289CT's horizontal stabilizer. N8686A taxied back to the gate. Post accident inspection of the airplane revealed minor damage to the right winglet.