7 Ways to Make Merry During a Holiday Weekend in Chicago's North Shore

Spend a festive weekend in Chicago’s North Shore looking at holiday lights, stocking up on sweets and shopping for gifts.

Holiday lights at Chicago Botanic Garden
Lightscape. Photo: Courtesy of Chicago Botanic Garden

If the wide tree-lined streets, stately homes and town squares of Chicago's northern suburbs look familiar, it's because places like Northbrook, Winnetka, Glencoe and Skokie have been the backdrops for many John Hughes films, including Home Alone. Starting in Evanston and stretching to the Wisconsin border, the North Shore pairs village vibes with urban amenities, rail access and proximity to Lake Michigan.

The neighborhoods' distinctly quaint architecture—wooden beams, gabled roofs, stucco walls—is the mark of Howard Van Doren Shaw, a pioneer of the early 20th century American Craftsman movement. His 1916 design for Lake Forest's Market Square rejuvenated its downtown and became the first planned shopping center in the U.S.

Lake Forest is the perfect base of operation for a winter weekend on the shore, basking in holiday lights, stocking up on sweets and shopping for gifts. It's home to Deer Path Inn, a Tudor-style, half-timbered hotel modeled after a 15th-century manor house in one of England's oldest villages. The inn opened in 1929 and welcomes guests with impeccable hospitality and amenities like an English garden and afternoon tea service.

Deer Path's Chief Spirits Officer Jorge Centeno develops the extensive cocktail list for the inn's restaurants and bars. His recipes—like the Christmas Cup, a Pimm's Cup twist with pomegranate, ginger and rosemary served in a snow globe—are personal and inventive. "I am inspired by everything," he says. "The seasons, holidays, places I have visited, scents and flavors I've enjoyed." Even if you don't stay overnight, make time for a nightcap here. After a day of exploring, a spot by the hearth and a Boozy Red Velvet Hot Chocolate hit just right.

7 Ways to Make Merry North of Chicago

01 of 07

Deer Path Inn

Hotel interior lobby with fireplace and Christmas tree
Courtesy of Deer Path Inn

Enhance a stay at the Deer Path Inn with a themed package. Lost in Lake Forest! includes an in-room viewing of Home Alone with gourmet popcorn, adult milkshakes, a box of chocolates from Sweet's in Lake Forest and Deer Path Inn robes (to take home!). Roll like Kevin McCallister in a Range Rover with complimentary round-trip transportation to Chicago Botanic Garden's holiday Lightscape (more on that soon). For a quiet night in, choose A Good Book and a Spot of Tea. Guests receive a title selected by the Lake Forest Book Store, bedtime snacks, a lavender mocktail or a trio of cocktails inspired by British authors, and a curated Sleepy Sips playlist.

02 of 07


Chicago Botanic Garden Lightscape
Lightscape. Courtesy of Chicago Botanic Garden

Illuminated trails create a magical landscape during the fifth annual Lightscape at Chicago Botanic Garden in Glencoe. This year, a reimagined walking path will transform new parts of the garden with creative works by international artists, like oversized lilies floating elegantly in the water and 19-foot-high lamp-shaped lights. But don't worry, Lightscape regulars: The beloved Winter Cathedral, an arched passage of 100,000 lights, will return this year.

Related: Great Places to See Midwest Holiday Lights

03 of 07

Winter Arts and Crafts Expo

Through December 20, support independent artists at Evanston Art Center's annual Winter Arts and Crafts Expo. The juried selection showcases nearly 150 creators and spans jewelry, ceramics, fiber, metal, glass, painting, photography and more. Founded in 1930, the Art Center offers youth and adult art classes, public lectures, and free gallery exhibitions year-round.

04 of 07

Santa Stops

Head to Glenview's Holiday in the Park and Parade on November 25 for hot cocoa, free kiddie train rides, a hayride and Santa. He and his helpers greet children at the end of the parade with a gift. Kids can also visit Santa and his reindeer while adults shop for greenery during the month of December at Chalet Nursery in Wilmette. Chalet also offers classes on bow making and holiday planters.

05 of 07

Take Flight Spirits

Cranberry-red cocktail with holiday decorating on table
Courtesy of Take Flight Spirits

Carrie and Andrew Cole opened Take Flight
in 2022 and have already released small-batch rum, gin and whiskey. Sample a flight in the Skokie tasting room or order a cocktail featuring house liqueurs and syrups. The peppermint-rum Kingdom of Sweets, or the Sugar Plum Fairy with gin, lemon, and vanilla-lavender butterfly pea syrup will
keep your mood merry and bright. You can also hone your mixology skills with a holiday cocktail class.

06 of 07


Pumpkin log cake roll at Hewn bakery
Hewn. Siege Food Photography

Snap up ginger or Neapolitan cookies (only available in December) at Hewn in Evanston, where every loaf, bun and bar is baked with locally sourced and milled grain. Co-owner and baker Ellen King says, "When December rolls around, we start playing holiday music to get into the spirit of things. The holidays on the North Shore are a special time, and we really enjoy it every year." Other seasonal staples include stollen, Birch de Nöel (Yule log), morning buns, and a deliciously sticky bourbon pecan pie, featuring whiskey from nearby FEW Spirits. The shop also sells giftable goodies and Midwest-milled flour for your own home baking.

Related: Top Things to Do Along Chicago's North Shore

07 of 07

Holiday Feasts

Get the holiday feasting going early. Spirit Elephant in Winnetka serves plant-based fare and whips up a vegan eggnog as creamy as any dairy 'nog. If you're full-time-fancy, book the opulent holiday tasting menu at George Trois. Chef Michael Lachowicz prepares ingredients like caviar, truffle, foie gras, lobster and squab with precision and avant-garde flair. Or make dinner your souvenir as you head home from the shore: Prairie Grass Cafe in Northbrook offers take-away meal packages starring dishes like braised short ribs. Choose fully cooked or ready-to-heat, and don't forget to add dessert. Chef Sarah Stegner makes Swedish ginger cookies and snowball cookies following her mom's recipes.

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