Enjoy the OPRF IWS Holiday Market. Shop unique holiday gifts, seasonal decorations, tasty treats, jewelry, stocking stuffers, hostess gifts and more from 22 local vendors. The market takes place in the upstairs event space of the IWS Children’s Clinic, 28 Madison Street in Oak Park.

Built in 1909 by E.E. Anderson, this rare rectilinear-style home blends elements of the Victorian and Prairie eras, making it unique to Oak Park. Inside, visitors experience a symbolic journey through Advent, as the home’s décor transitions from darkness into light. A shining example of classic renovation, this home seamlessly integrates modern updates while preserving its original character.

Step inside this magical Mid-Century home, a 1965 masterpiece originally commissioned by a local mobster, and be transported to a Rat Pack–era Christmas. The home’s design, paired with traditions and décor—including treasured ornaments, holiday music boxes, and a one-of-a-kind Christmas Village—evokes the feel of a festive soirée straight out of a classic Hollywood film.

This three-story Prairie-style estate, designed in 1915 by architect H.G. Fiddelke, exudes holiday charm on every level. On the upper floor is a custom log cabin, added in 1925 and now marking its 100th anniversary. Complete with a Prohibition-style speakeasy, the cabin reflects the home’s storied past. The true magic lies in the holiday traditions that come alive within its walls.

Nestled on a sprawling corner lot, this grand River Forest estate is an architectural masterpiece. Experience the magic of the holidays with six fireplaces, two Christmas trees, treasured heirlooms, and an original recreation hall transformed into a dining room—perfect for festive gatherings. The estate’s charm is enhanced by its original player organ, stunning fresco paintings, and a host of timeless design features.