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Meet Dr. Jessica Freilich

Chicago Therapist Serving Illinois & PSYPACT States

You’ve been holding it all together for so long that even asking for help feels like another task. You’re thoughtful, capable, and used to figuring things out on your own, but lately, it’s not working. Maybe you feel stuck in old patterns, overwhelmed by change, or exhausted from taking care of everyone else. You want to feel more like yourself again, but you’re not even sure where to begin. Therapy is a place for us to figure all that out together. 

I’m Dr. Jessica Freilich, a Chicago therapist helping people slow down, tune in, and heal, so they can move through life with a deeper connection to themselves.

My Approach to Therapy

I help people who feel anxious, stuck, disconnected, or overwhelmed reconnect with themselves and what matters most to them.

Therapy works best when it’s grounded in a real relationship, one where you feel heard, understood, and gently challenged. My style is warm, collaborative, and active. I won’t just nod and smile at you. I’ll show up fully, bring curiosity and compassion to our conversations, and help you explore what’s keeping you stuck.

I draw from psychodynamic and attachment-based frameworks, which means I help clients uncover patterns that developed in earlier relationships and continue to play out today. Understanding those patterns gives us more freedom to respond, rather than react. I also integrate practical, present-focused strategies from approaches like CBT and mindfulness to help you cope with anxiety, self-doubt, and emotional overwhelm in your daily life.

If you’re someone who tends to overthink, people-please, or feel like you have to keep it all together, therapy can help you begin to let go of those burdens and reconnect with yourself and the life you want.


What It’s Like to Work Together

My style is warm, attuned, and collaborative. I’ll bring curiosity, care, and a healthy dose of honesty into the room with you. I value humor, humanity, and creating a space where you can feel more like yourself. Part of how I do this is by showing up as my genuine self as well. 

In our work together, you can expect:

  • A supportive relationship

  • Space to reflect on the past and how it’s shaping your present

  • Practical skills to help manage what’s overwhelming right now

  • Honest feedback and gentle challenges to help you grow

  • An opportunity to feel less alone in what you’re carrying

You Can Come Just as You Are


I offer a space where you don’t have to be “fine.” Your full experience is welcome, your uncertainty, grief, confusion, joy, anger, and everything in between. You can show up messy, in progress, not quite sure what you need. We’ll figure it out together.

Clients often tell me they appreciate how present and engaged I am. I ask thoughtful questions, listen closely for what’s not being said, and offer insights that help connect the dots. I also believe in the power of humor and humanity. We’re doing meaningful work, but that doesn’t mean we can’t laugh along the way.

I see therapy as a space not just to manage symptoms, but to grow. To explore who you are, how you got here, and what you want your life to look like moving forward.

Who I Work With

I support the deep feelers, high achievers, parents, caregivers, and cycle-breakers, helping them find steadiness amid stress, change, and self-doubt. My clients come to me when they’re tired of overthinking, people-pleasing, or holding in their emotions, and ready to build a more grounded, authentic relationship with themselves.

I specialize in working with adults navigating:

  • Anxiety, chronic stress, or emotional overwhelm

  • Major life transitions (career changes, relocation, breakups, identity shifts)

  • Difficult family or relational dynamics

  • Parenthood, whether you're planning, pregnant, postpartum, or parenting older kids

  • Trauma, including relational or childhood trauma

  • Patterns of self-criticism, perfectionism, or people-pleasing

Some of my clients are new to therapy. Others have been before, but are ready for deeper, more meaningful work. What they share is a desire to understand themselves more fully and create lasting change.

A Little More About Me

Before starting my private practice, I worked in a range of settings from group practices, community mental health clinics to therapeutic schools and inpatient hospitals. These experiences helped shape my understanding of how trauma, attachment, and identity intersect with mental health.

I'm naturally curious, which has led to becoming a lifelong learner about the world and the people around me. As a mom of three, I deeply appreciate how complex and humbling it is to care for others while still trying to care for yourself. I bring my lived experience into my work, along with deep respect for the vulnerability it takes to show up and ask for support.


Ready to Begin? 

If you’re looking for a Chicago therapist who meets you where you are with warmth and curiosity, and helps you move toward where you want to be—I’d love to connect.

The first step is a free 15-minute consultation. It’s a chance for us to talk, see if it feels like a good fit, and answer any questions you have about therapy.

I offer online therapy across Illinois and PSYPACT states.


I look forward to connecting with you!

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