FREE 6 Month TripIt Pro Subscription Posted On March 23, 2020 Get a FREE 6 Month TripIt Pro Subscription! TripIt Pro is a $49/year service to help you keep track of your travels.If you’re new to TripIt, sign up between March 13 and March 31, and we’ll automatically give you access to TripIt Pro for six months.If you’re using our free TripIt service, update your account by March 31. For existing TripIt Pro users, we’ll be extending the same value to you.