Volume I Issue 02: Chicago, The Holiday Edition

Where the cold is decorated

The Note

Chicago during the holidays is magic. Millennium Park’s Christmas tree lighting on November 21 marks the official start of winter celebration.

Walking down Oak Street, the wind off of Lake Michigan cuts through the layers, but the cold is softened by the lights strung through bare trees, wreaths hung on limestone doorways, red velvet bows tied around lamp posts, and twinkling evergreen trees in boutique windows. The festive atmosphere transforms the cold into something worth celebrating.

This is Chicago’s holiday gift. The city celebrates the cold, creating beauty against the gray skies. Steel towers reflect the holiday displays, multiplying light against early darkness. The contrast of the bitter cold and warm light creates the magic that only exists in a city that truly understands winter.

The Escape

The Drake Oak Brook

Thirty minutes west of downtown Chicago, nestled amongst quiet estates sits The Drake Oak Brook. The location is strategic. Close enough to access the city’s energy, yet far enough to guarantee actual quiet when you need it. The hotel opened in 1961, an era when hotel architecture meant permanence and grandeur. Frank Sinatra stayed here. So did Prince Charles.

The recent renovation understood what to preserve and what to update. Crystal chandeliers and velvet chaises appear throughout, from the lobby to guest rooms. The original grandeur has been maintained but updated with contemporary details. Rooms favor a blue-grey palette that reads sophisticated without trying too hard. A chandelier provides soft central lighting, creating a warm, elevated mood. Marble bathrooms carry through the refined elegance.

The hallways during the holiday season strike the right balance of timeless and seasonal. Evergreen garlands and silver lights carefully placed through the hallways, a curated take on Midwestern hospitality.

The Oak Brook location means easy parking, quiet and stillness, and the freedom to move between city immersion and suburban respite. A car is useful here. Not just for getting to the city but also helpful for city exploration in the cold.

Starting at $200 for the deluxe guest room during the holidays.

The Table

Kasama

Kasama is the reason people stand in below-freezing temperatures. The Filipino bakery-restaurant in the East Ukrainian Village has a brunch line that wraps around the block on weekends, even in the winter.

The standouts explain why the hour-long wait in the cold is worth it. The ube and coconut ensaymada is an elevated spin on the classic Filipino pastry, sweeter and more interesting than your typical confection. The foie gras danish is rich without being heavy. The pork belly adobo is the perfect balance of vinegar and soy to be refreshing. Order the ube latte with whatever you’re eating. The yam’s earthiness mixed with the sweetness of coconut, along with the playful purple color, can brighten any gray Chicago day. The dinner course is on the Eature return list. No reservations for daytime service. Insider tip: skip the line entirely and order ahead for takeout.

The Eature Return List:

The best cities require multiple trips to reveal each layer. Here is my wishlist for the next trip:

Kasama Dinner Service: The same team behind the brunch line runs a different operation in the evening. Filipino tradition meets French technique in tasting menus. This is the version of Kasama that was awarded the coveted Michelin star. $325 per person. Book reservations 45 days in advance.

Au Cheval: Originating in Chicago’s West Loop, Au Cheval is an elevated diner experience. The space features warm brown leather and soft lighting, the perfect contrast to winter. A Chicago-native insisted on this recommendation with genuine enthusiasm. There are no reservations, expect a wait.

Elske: Another gem in the West Loop with tasting menus inspired by Danish cuisine. The space itself feels Nordic despite its location in Illinois with smooth brown wood, clean lines, and natural light. The Nordic influences in taste and design make it the perfect accompaniment to a meditative winter. $140 per person.

The Edit

Start the morning on Oak Street. The cold clears the crowds of casual browsers, and a stroll past the boutiques with their matching brand facades feels meditative. Stop at Le Labo on your stroll to pick up a small gift for yourself or a loved one. A reflection of Chicago jazz, Baie Rose 26 is Chicago’s exclusive scent and smells of a blend of sweet rose geranium with the musk of pink peppercorn. Light, a hint of sweet with the sophistication of Le Labo, it smells of warm jazz accompanying a winter evening.

Moving South, the Starbucks Reserve Roastery offers unique gifts for collectors from reserve roastery exclusives to Chicago-branded items. This isn’t your typical corner Starbucks. Sitting at five stories, this location is the largest Starbucks in the world, functioning as both an architectural statement and coffee theater. Take a break to sip seasonal espresso martinis on the fourth floor. Find a seat by the tilted floor-to-ceiling windows and look down at Michigan Avenue below. The holiday displays spread out like a lit stage. You can appreciate the choreography of holiday shoppers away from the crowds.

When you’re in Chicago during this time of year, a stop at CB2 should be in order. Originally founded in Chicago, CB2’s holiday shop offers modern, curated seasonal design for those who resist traditional decor. Think holiday decoration with clean lines and muted color palettes. Subtle, timeless, and refined. Come for inspiration, even if you don’t buy. The styling feels aspirational in an achievable way.

Tucked in Chicago’s West Loop, Moth provides necessary contrast to the large commercial flagships. This is a small, carefully edited boutique with homewares of Japanese and Nordic influences. The color palette is minimal with emphasis on shape, texture, and craft. This is where you find the gift for someone who notices craft.

Next issue: Volume I Issue 03: Kyoto. Arrives Sunday, December 14, 2025.

Eature is written for those who care about where they stay, why a place feels the way it does, and how travel fits into a life well-lived.

New here? Read about how Eature works

More Eature Guides: Tokyo | Kyoto | Osaka | Chicago | Denver | Orange County