Grief During the Holidays: Supporting Yourself and Your Family in Chicago

The holidays are often portrayed as a time of joy, togetherness, and celebration. But if you’ve lost a family member or are navigating another significant loss, the holiday season can instead feel heavy, disorienting, or painfully quiet. While others are planning parties or traditions, you might be just trying to cope with grief and get through each day.

If that’s where you find yourself this year in Chicago, you’re not alone—and there is nothing wrong with you for struggling. Grief changes how we move through this season, and it’s okay for your experience to look different than it used to.

We support individuals and families across River North, Lakeview, Northbrook, and surrounding Chicagoland communities who are facing grief during the holidays and looking for ways to honor both their love and their pain.

Why the Holidays Can Feel So Hard

Grief is present all year, but the holidays often have a way of amplifying it. You may be:

• Missing traditions you used to share with a loved one
• Feeling out of place at gatherings or choosing to skip them altogether
• Noticing the empty chair at the table or the silence where their voice used to be
• Comparing this year to “before” and feeling like nothing is the same

Memories, music, familiar places, and even simple routines can trigger waves of emotion. This is a difficult time, and it makes sense if your heart feels pulled in many directions.

Giving Yourself Permission to Grieve

One of the most important steps is allowing yourself to feel what you feel—even when it doesn’t match the mood around you.

You’re allowed to:

• Say no to events that feel overwhelming
• Leave a gathering early if you need to
• Cry, laugh, or feel numb—all of these are normal responses
• Do less this year instead of pushing through as if nothing has changed

Grief has no timeline and no “right” way to move through it. Being honest with yourself about your needs is a key part of learning to cope with grief.

Creating Gentle, Meaningful Rituals

Sometimes, small rituals can feel comforting in the midst of grief. They don’t erase the pain, but they can create a sense of connection and intention.

Some families in Chicago find meaning in:

• Lighting a candle in honor of the person who died before a meal or gathering
• Sharing a favorite memory or story
• Playing a song or making a recipe that reminds you of them
• Creating a small space in your home with photos or mementos

You get to decide how visible or private these rituals are. The goal isn’t to “make it all better,” but to acknowledge the love that remains.

Supporting Your Family Through Holiday Grief

When you’re grieving and also trying to support others—children, a partner, or extended family—it can feel especially complicated. Different people grieve in different ways: one family member may want to talk often, while another may withdraw or focus on staying busy.

A few helpful ideas:

• Check in gently: “How are you feeling about the holidays this year?”
• Let kids know it’s okay to feel sad and still enjoy parts of the holidays.
• Consider adjusting traditions rather than canceling everything—small changes can reduce pressure.

If emotions feel particularly intense or conflict is rising, it may be helpful to involve a therapist who can support the whole family.

You Don’t Have to Do This Alone

For many people, connecting with others who understand can be a lifeline. A support group or individual therapy can offer a space to talk openly about your loss, your fears, your anger, and your longing—without needing to “be okay” for anyone else.

At Wellington Counseling Group, our clinicians provide grief counseling for individuals, couples, and families in the Chicagoland area and surrounding suburbs who are navigating grief during the holidays and beyond. We can also help you explore whether a local support group might be a helpful addition to your care.

Reaching Out for Support in Chicago

You don’t have to pretend this season is easy. Grief is a natural response to love, and it deserves care, not avoidance.

If you’re struggling with grief during the holidays, contact us to schedule a confidential appointment. Together, we can create space for your grief, your memories, and your healing—one step at a time.