December Hotels

Question

Arriving Mid-December for a 3 night stay to get in the Holiday Spirit. Debating between The London House, The Drake, and Pendry Hotel. Which would you recommend? Holiday Decor a plus, but also expect to have a comfortable stay. Thanks!

Answer

Mid-December is one of the most festive times to visit Chicago, and all three hotels on your list—LondonHouse, The Drake, and the Pendry—offer a mix of holiday ambiance, comfort, and great locations. The best fit really depends on what kind of experience you want: classic and nostalgic, modern and stylish, or upscale with a dramatic skyline feel.

Each property has its own personality during the holidays. The Drake leans into traditional elegance, LondonHouse offers stunning river and skyline views with a polished modern feel, and the Pendry provides a chic, boutique experience inside a historic building. All are comfortable for a three-night stay, but their holiday decor styles and typical guest experience differ.

Here’s a breakdown to help you choose the best option for getting into the holiday spirit while enjoying a relaxing stay.

The Drake Hotel — Best for classic holiday charm and historic Chicago ambiance. Expect traditional Christmas decor, an old-world feel, and a prime location near the lake and upscale shopping. Rooms lean traditional, not modern, but are comfortable and quiet. Great holiday atmosphere overall.
LondonHouse Chicago — Best for modern luxury and incredible views. Holiday decorations are elegant but not as elaborate as the Drake’s. The rooftop (even in winter) and riverfront location make it ideal if you want a “big city holiday” vibe. Rooms are stylish and contemporary.
Pendry Chicago — Best for boutique elegance and design-forward comfort. Located in the historic Carbide & Carbon building, the Pendry adds tasteful, modern holiday touches rather than going all out. Rooms are plush, refined, and quieter than many downtown hotels. Excellent service and a cozy atmosphere.

If holiday decor is a high priority, The Drake wins for its traditional Christmas feel. If skyline views and city sparkle matter more, LondonHouse is hard to beat. If you want a comfortable, sophisticated retreat with a curated holiday ambiance, Pendry is the best fit.

A few quick additional considerations: LondonHouse tends to feel the busiest in December because of its location and popularity; The Drake is festive but more relaxed; Pendry offers the quietest and most intimate stay. All three offer quick access to holiday attractions like the Magnificent Mile Lights, Millennium Park, and the Christkindlmarket.

Best Overall Holiday Atmosphere: The Drake
Best for Views and Modern Style: LondonHouse
Best for Boutique Comfort and Relaxation: Pendry

Overall, for pure holiday spirit and a classic Chicago Christmas experience, The Drake is the strongest choice. For a sleek, city-sparkle setting, choose LondonHouse. For a refined, cozy, modern getaway, go with the Pendry.

No matter which you choose, you’ll be well located and surrounded by festive city highlights, making it a great mid-December trip.