Battling Chicago’s midwinter chill, Hamish Kilburn found solace in the city’s most stylish hotel stays – where bold design and warm hospitality proved to work in all seasons…
Chicago, in the depths of winter, is not for the faint-hearted. With icy winds whipping off Lake Michigan and temperatures plummeting to -20°C, the city demands resilience – and a well-curated wardrobe. But beyond the frostbitten streets and snow-dusted skyline, a different kind of warmth awaits. Tucked behind grand façades and unassuming entrances, Chicago’s new wave of design-led hotels are redefining luxury, proving that style and substance can thrive even in the coldest of climates.
From gilded Art Deco masterpieces to sleek, modernist sanctuaries, these hotels offer more than just a place to thaw out. They are immersive spaces where bold aesthetics meet meticulous craftsmanship, where every corner tells a story and where hospitality is an art form in itself. As I navigated the city’s chill, stepping into these havens felt like entering another world – one where the design was as rich and layered as Chicago’s own history.
Image credit: Viceroy Hotel Group
Viceroy Chicago
If Viceroy were a person, it would be that effortlessly cool friend who always knows the best restaurants before they’re trending, wears designer with a devil-may-care attitude, and somehow makes even a simple espresso feel like an event. Bold yet refined, playful yet poised, Viceroy is more about living in the moment than luxury statement. It’s got style, charisma, and just the right amount of rebellion. So, when the brand set up shop in Chicago, a city known for its architectural bravado and artistic soul, it was only natural that Viceroy Chicago would embody the same fearless elegance – with a distinct Windy City edge.
“A hub for culture, cuisine, and style,” is how Bill Walshe, CEO of Viceroy Hotel Group, described it when it opened in 2017. Viceroy Chicago effortlessly owns its position, 18 stories into the skyline. A modern-day flâneur’s dream, this urban retreat is where bold design meets effortless cool, a place where detail, from the Marcel Proust-inscribed Poem Wall to the mid-century-inspired guestroom headboards, whispers a story of discovery. And then there’s the rooftop – home to the neighbourhood’s first rooftop pool, where sunset cocktails come with a side of glittering cityscape views.
Image credit: Hoxton
The Hoxton, Chicago
If Viceroy is the ‘in the know friend’, Hoxton on the other hand is the one that has bailed on the status quo to gatecrash the underground scene instead. Nestled in the heart of Fulton Market, the hotel channels the neighbourhood’s industrial past with exposed brick, brass accents, and mid-century furnishings – so Hoxton – yet there’s nothing predictable about it. The lobby hums with creatives tapping away on MacBooks by day and clinking cocktails by night, while upstairs, the rooftop pool and Peruvian-inspired Cabra restaurant keep the energy high.
Image credit: Cindy's Rooftop
Chicago Athletic Association, part of Hyatt
While the rooms at the Chicago Athletic Association, part of Hyatt, carry a quirky charm with a touch of vintage nostalgia, it’s the hotel’s unbeatable location that truly shines. But the real star of the show? Cindy’s Rooftop – the bar and restaurant that has cemented itself as the ‘it girl’ of Chicago’s hospitality scene. Overlooking Millennium Park, the space transforms with the seasons – an intimate winter retreat warmed by glowing fire pits, and in summer, a breezy, sun-drenched hotspot.
Editor’s tip >> If you are unable to book a table at Cindy’s – or fancy something more affordable – head a few doors over, on street-level, to a delicious Italian called Acanto!
Image credit: Publishing House / Joshua Haines
The Publishing House Bed and Breakfast
If you’re looking for something different, the kind of place where literary charm meets modern luxury, The Publishing House Bed and Breakfast is served! Sheltered in a former publishing warehouse, this intimate, indy boutique B&B oozes character with its exposed brick walls, vintage typewriters and shelves stocked with an eclectic mix of books.
Each room feels like a cozy, curated hideaway – personalised yet impeccably stylish. With just a handful of rooms, the experience is as much about the thoughtful details as it is about the welcoming, homely vibe. Guests can enjoy a delicious, locally sourced breakfast before setting off to explore the vibrant West Loop, making it the perfect blend of comfort, creativity and community.
Image credit: Pendry Hotels
Pendry Chicago
Hotels these days are more about what’s on the inside than anything else. But that’s not the case at Pendy Chicago. Housed in the stunning Beaux-Arts Carbide & Carbon Building, the hotel blends timeless and quiet architecture with sleek, contemporary design.
Inside, the vibe is effortlessly chic – think polished marble, plush velvet and gold accents that exude understated luxury. The hotel’s rooftop bar, with sweeping views of the Chicago skyline, is a hotspot for both guests and locals, offering a lively atmosphere to sip cocktails as the city buzzes below. With its artful mix of style, service, and location, Pendry Chicago is as much about the experience as it is about the destination itself, offering a sophisticated retreat in the heart of the bustling city.
Image credit: The Gwen Hotel | Marriott International
The Gwen
At first glance, the Gwen Lux Suite at The Gwen is the epitome of refined elegance – a sprawling sanctuary with a dedicated dining room, two plush bedrooms and expansive marble-clad bathrooms, which boasts the ‘best view of Downtown’. But the real magic happens beyond its gilded interiors. Step onto the private terrace, and the suite transforms into an ultra-glamorous glamping retreat.
During the summer months, a billowing luxury tent takes centre stage, adorned with jute rugs, bongo bedside tables and softly glowing lanterns, creating a dreamlike escape high above the city. Turndown service swaps the traditional mint for an artisanal s’mores kit, while a bespoke glamping tasting menu elevates the outdoor experience to decadent new heights. Think wilderness reimagined – Chicago-style.
Image credit: Peninsula Hotels
Peninsula Chicago
The Peninsula Chicago is a world of marble, silk, and a touch of magic. Positioned on Michigan Avenue, it feels like stepping onto a glamorous 1930s movie set—if the plot centered on indulgence and flawless service. Plush rooms (and bathrooms) boast stunning views of the skyline and Lake Michigan, while the rooftop pool makes you feel as though you’re floating above the city. With a spa to match, the hotel, like all others in the Peninsula portfolio around the world, effortlessly blends old-school luxury with modern cool, carving out its own iconic identity in the city’s competitive landscape.
> Since you’re here, why not read about Gili Langkanfushi, a hotel in the Maldives that will leave you shipwrecked yet chic…
Main image credit: The Gwen
