5 Bucket List Hotels in Chicago
When choosing a place to stay, I am drawn to more than just comfort. I look for atmosphere, design, and a sense of place that reflects the city itself. Chicago’s luxury hotels are defined by character and craftsmanship, each offering a distinct interpretation of sophistication. These properties stand out not only for their architecture and interiors, but for the way they invite you to slow down and experience the city in a more intentional way.
1. The Pendry Chicago – For the Modern Classicist
Set within the iconic Carbide & Carbon Building, The Pendry Chicago brings contemporary elegance to one of the city’s most celebrated Art Deco landmarks. Rising 503 feet, the emerald-green tower, accented with real gold leaf, is a striking presence on Michigan Avenue. Inside, the design is a blend of moody sophistication and modern restraint, with rich textiles, sculptural lighting, and interiors that feel at once historic and refreshingly current. On the ground floor, Bar Pendry channels old-world glamour with a contemporary twist, while Venteux offers a Parisian-inspired dining experience that is effortlessly chic.
Why It’s Bucket List Worthy:
The Pendry captures the spirit of modern Chicago, stylish, rooted in history, and quietly luxurious. Housed in a landmark building, it balances architectural grandeur with thoughtful design, creating a stay that feels both iconic and inviting. Every element, from the textures to the lighting and personalized service, encourages you to slow down and savor the experience. It is a hotel that rewards a keen eye and a relaxed pace, making it ideal for travelers who value both heritage and modern comfort.
Benefits of The Pendry include:
Central Location: Situated on Michigan Avenue, steps from Millennium Park, the Riverwalk, and world-class shopping and dining
Spacious Suites: A rarity in downtown Chicago, suites range up to 1,033 square feet, with specialty layouts that offer extra space and comfort
Impressive Views: Select rooms offer striking views of the city skyline and iconic landmarks, including the Wrigley Clock Tower
Distinctive Dining: Enjoy refined cocktails at Bar Pendry or French-inspired cuisine at Venteux, all in beautifully designed, atmospheric settings
2. The Waldorf Astoria Chicago – For the Sophisticated Traveler
Tucked into the heart of Chicago’s Gold Coast, The Waldorf Astoria Chicago is a refined retreat that blends Parisian-inspired grandeur with understated Midwestern warmth. With its stately limestone façade, cobblestone motor court, and graceful art deco touches, the hotel feels more like an elegant private residence than a traditional city stay. Inside, high ceilings, custom furnishings, and a soothing, neutral palette create an atmosphere of effortless sophistication.
The guest rooms and suites are among the most spacious in Chicago, offering residential-style comfort with features such as fireplaces, private terraces, and oversized marble bathrooms with deep soaking tubs. At the heart of the hotel, the reimagined lobby-level Brasserie serves classic French cuisine in a chic, welcoming space, perfect for leisurely brunches or intimate dinners.
Why It’s Bucket List Worthy
The Waldorf Astoria Chicago is the epitome of sophisticated urban luxury, timeless, and serenity. The hotel is designed for travelers who appreciate elegance, comfort, and exceptional service. From the moment you arrive, every detail feels intentionally curated, from the soft scent in the air to the feel of the linens and the thoughtful, personalized service. With expansive accommodations, a tranquil spa, and elevated dining, the experience is indulgent, memorable, and uniquely refined.
Benefits of Waldorf Astoria include:
Prestigious Location Located in the Gold Coast neighborhood, just steps from luxury shopping, historic mansions, and the lakefronts
Spacious Suites Accommodations up to 2,400 square feet, many with private terraces, fireplaces, and residential touches rarely found downtown
Wellness and Spa A full-service spa and wellness center featuring steam rooms, an indoor lap pool, and a range of treatments designed for relaxation and renewal
Refined Dining Brasserie offers modern French cuisine in a sunlit setting, while in-room dining brings restaurant-level quality to the comfort of your suite
3. Loews Chicago Hotel, For the Contemporary Traveler
Set in the lively Streeterville neighborhood, Loews Chicago Hotel blends sleek design with inviting comfort just steps from Navy Pier and the Riverwalk. Its glass tower rises above the city, offering panoramic views of the skyline and Lake Michigan through floor-to-ceiling windows in every room. Inside, the mood is contemporary and relaxed, with curated art, natural finishes, and thoughtful amenities throughout.
Guests can unwind on the rooftop terrace with fire pits and skyline views, recharge in the indoor lap pool and fitness center, or dine at ETA Restaurant, where seasonal American dishes are served in a warm, modern space.
Why It’s Bucket List Worthy
Loews Chicago is stylish yet approachable, ideal for travelers who want downtown energy paired with elevated comfort. Key highlights include:
Central Location Walkable to Navy Pier, Millennium Park, and Michigan Avenue
Stunning Views Expansive windows bring in light and iconic cityscapes
Rooftop Vibes A third-floor terrace with fire pits and seasonal events
Thoughtful Dining Modern American fare inspired by local flavors at ETA
4. The Gwen, a Luxury Collection Hotel, For the Design Enthusiast
Located just off Michigan Avenue, The Gwen pays homage to the golden age of Chicago design while offering a contemporary, art-forward experience. Named after sculptor Gwen Lux, whose work adorns the building’s façade, the hotel is a masterclass in blending vintage glamour with modern sophistication. The interiors feature mid-century influences, jewel-toned accents, and bold architectural details that echo the city’s creative spirit.
The hotel’s terrace, one of the largest in the city, offers panoramic skyline views and serves as a social hub for cocktails and conversation under the stars. Inside, Kostali by Naha delights guests with Mediterranean-inspired cuisine that feels both elevated and effortlessly inviting.
Why It’s Bucket List Worthy:
The Gwen captures Chicago’s enduring relationship with art, architecture, and style. Every element, from the sculptural décor to the curated lighting and textured materials, feels intentional and inspired. For those who appreciate design-driven luxury and a strong sense of place, The Gwen offers an experience that is as visually captivating as it is comfortable.
Benefits of The Gwen include:
Prime Location: Situated directly on Michigan Avenue, steps from the Magnificent Mile, Millennium Park, and premier shopping and dining
Distinctive Design: A celebration of Art Deco artistry blended with modern luxury and creative flair
Expansive Terrace: One of downtown Chicago’s most striking outdoor spaces, ideal for evening drinks or weekend brunches
Inspired Dining: Kostali by Naha features a menu rooted in coastal Mediterranean flavors, served in an elegant, contemporary setting
5. Omni Chicago Hotel, For the Classic Urban Explorer
Perfectly positioned on the Magnificent Mile, the Omni Chicago Hotel offers timeless comfort and refined hospitality in the heart of the city. The all-suite property combines classic style with modern amenities, creating an inviting retreat above the bustle of downtown. Each suite features a spacious living area, plush bedding, and large windows framing views of Michigan Avenue or the surrounding skyline.
Inside, the design is understated yet elegant, with warm tones, tailored furnishings, and thoughtful touches that make each stay feel personal. The hotel’s restaurant, 676 Bar & Lounge, showcases locally inspired American cuisine and craft cocktails, making it an ideal spot to unwind after a day of exploring.
Why It’s Bucket List Worthy:
The Omni Chicago delivers an authentic city experience with the comforts of home. Its all-suite design, attentive service, and unbeatable location make it a favorite for travelers who want to experience Chicago’s energy without sacrificing tranquility. It is the perfect balance between urban excitement and relaxed sophistication.
Benefits of the Omni include:
Exceptional Location: Situated along the Magnificent Mile, within walking distance to top attractions, theaters, and restaurants
All-Suite Comfort: Every accommodation offers separate living and sleeping areas for a spacious, residential feel
Modern Amenities: Fitness center, indoor pool, and access to Omni’s signature Select Guest loyalty perks
Local Flavor: 676 Bar & Lounge highlights Chicago’s culinary creativity with dishes made from locally sourced ingredients
