The 64 Best Boutique Hotels with Entertainment in Lake Michigan (2025)

Nestled in the vibrant heart of Milwaukee, Kinn Guesthouse Downtown exudes a romantic allure with its midcentury modern art deco design. As you step into this luxurious haven, the scent of freshly brewed Nespresso wafts through the air, inviting you to unwind in an ambiance that beautifully marries comfort and sophistication.

Chic Urban Retreat - Immerse yourself in stylish surroundings where high ceilings and sleek furnishings create a serene escape from the city's hustle and bustle, perfect for couples seeking a romantic getaway or luxury seekers indulging in a sophisticated experience.

Inviting Communal Spaces - Enjoy the warmth of shared spaces that beckon you to relax; whether it's a leisurely afternoon in the cozy lounge or a lively gathering in the modern kitchen, these thoughtfully designed areas encourage connection and camaraderie among friends and loved ones.

Exceptional Location - Situated just moments away from Milwaukee's cultural gems, delight in the convenience of exploring local markets, theaters, and dining spots—all within a pleasant stroll from your doorstep, making every outing a memorable adventure.

Guest Experiences - As guests settled into their spacious rooms, they were enchanted by the stunning city views framed by tall windows, while the soft hum of laughter and clinking glasses from the communal kitchen hinted at delightful conversations waiting to unfold over light snacks and Nespresso.

Nestled in the vibrant heart of Milwaukee, The Pfister Hotel transcends the ordinary with its exquisite blend of historic charm and modern luxury. As you step into this opulent haven, the scent of fresh blooms mingles with the subtle echoes of soft jazz, inviting you to unwind in an atmosphere steeped in elegance and romance.

Total Relaxation - Indulge in a rejuvenating escape at the full-service spa, where the gentle sound of flowing water accompanies your journey to tranquility. Each treatment is tailored for blissful relaxation, allowing you to fully immerse yourself in self-care amidst opulent surroundings.

Outstanding Location - Just a leisurely stroll from the iconic Milwaukee Art Museum, The Pfister places you at the center of cultural exploration. With the city's vibrant art scene and lively markets within easy reach, every moment spent here is infused with local character and charm.

Romantic Break - Elevate your getaway with breathtaking views from Blu, the martini bar perched high on the 23rd floor. Sip on expertly crafted cocktails as the sun sets over the city skyline, enveloping you in a warm glow that perfectly complements a dreamy evening.

Guest Experiences - One guest reminisced about the delightful breakfast in the cafe, describing the aroma of freshly brewed coffee and warm pastries wafting through the air, paired with attentive service that made them feel like royalty. Another was captivated by the intricate details adorning the lobby, feeling as though they were stepping into a living museum where each corner revealed a story.

Nestled in the heart of Chicago, The Langham exudes a sophisticated elegance that invites guests to indulge in a world where luxury meets unparalleled service. This architectural marvel, designed by Mies van der Rohe, offers a serene retreat just moments from the vibrant energy of Michigan Avenue, ensuring every moment spent within its walls feels like a cherished escape.

Romantic Hideaway - With warm tones and dark wood accents, the rooms create an intimate ambience, enhanced by floor-to-ceiling windows framing stunning views of the city skyline and shimmering Lake Michigan, making each moment feel like a scene from a romantic film.

Spa and Wellness Retreat - Chuan Spa beckons with its soothing aromas and tranquil atmosphere, offering rejuvenating treatments inspired by Traditional Chinese Medicine that promise to melt away stress and transport you to a place of serenity, especially after a long day of city exploration.

Culinary Delights - At Travelle, seasonal American cuisine is presented with flair, infusing modern flavors into traditional favorites, while the elegance of afternoon tea at Pavilion invites you to savor exquisite Langham teas paired with delightful sweet and savory treats, amidst the gentle sound of clinking cups.

Guest Experiences - Upon arrival, the sweet scent of freshly brewed tea wafts through the air as guests recount their first impressions—a delightful champagne tea greeted them, followed by the plush comfort of impeccably clean rooms, where soft linens invite you to sink into relaxation, punctuated only by the faint sounds of laughter from the bar below.

Nestled just six blocks from the iconic home of former President Obama, Sophy Hyde Park invites you into a world where art, literature, and music intertwine within a refined, eclectic ambiance. Here, every corner resonates with creativity, offering an intimate escape immersed in the rich culture of Chicago's Hyde Park neighborhood.

Artworks - Every inch of Sophy Hyde Park tells a story through vibrant local art. As you wander the halls, you'll encounter striking pieces that spark conversation and inspire wonder, creating a living gallery that showcases the spirit of the community.

City Style - The hotel embodies a chic, boutique aesthetic, boasting hardwood floors underfoot and plush lounge seating that beckons you to relax. It's a perfect blend of elegance and warmth, inviting guests to unwind while savoring the unique character of each space.

Total relaxation - Indulge in luxurious comforts in your guest room, featuring marble-tiled bathrooms and cozy seating areas. Some rooms even offer a separate living space, ideal for quiet evenings spent sipping from the fully-stocked mini-bar as you take in the tranquil atmosphere.

Guest Experiences - Guests have remarked on the delightful scent of polished wood mingling with the soft crackle of the double-sided fireplace in the lobby, providing a welcoming ambiance. One visitor fondly recalled how the friendly staff would always greet them with warm smiles, making their stay feel like a homecoming rather than just a getaway.

Nestled in the vibrant heart of Chicago, Nobu Hotel invites you into a realm where contemporary luxury meets serene indulgence. With its sleek design and intimate ambiance, this elegant escape is a sanctuary for couples seeking romance, wellness enthusiasts yearning for relaxation, and cultural explorers ready to dive into the city's rich tapestry. Here, every detail is crafted to delight the senses, from the soft rustle of silk sheets to the tantalizing aromas wafting from the on-site restaurant.

Romantic Retreat - Slip away into an oasis designed for love, where beautifully appointed rooms feature plush bedding and ambient lighting that set the mood for unforgettable evenings. The hotel’s intimate nooks beckon for cozy conversations over cocktails, perfect for newlyweds or those rekindling a spark.

Culinary Excellence - Awaken your palate with extraordinary dining options that fuse American and Asian flavors, expertly prepared by renowned chefs. Guests rave about the breakfast, often described as one of the best they've ever experienced, featuring delightful dishes that leave lingering tastes of culinary artistry.

Wellness Oasis - Unwind in a tranquil haven equipped with state-of-the-art fitness facilities, a rejuvenating indoor pool, and a sauna that envelops you in soothing warmth. The spa facilities promise total relaxation, allowing weary travelers to indulge in treatments that restore balance and peace.

Guest Experiences - Upon entering their room, guests have been greeted with a thoughtful welcome letter and chilled champagne, setting a celebratory tone for their stay. One particularly impressed visitor noted the surprisingly comfortable bed, while the gentle hum of city life outside created a perfect backdrop for restful nights.

Nestled in the heart of Chicago, where the iconic Magnificent Mile meets an artistic sanctuary, Hotel EMC2 offers a harmonious blend of sophistication and comfort. This chic boutique hotel invites you to indulge in a vibrant atmosphere, with carefully curated art pieces enhancing your surroundings, making each moment feel uniquely special.

City Style - Immerse yourself in the pulse of downtown Chicago, surrounded by designer shops, gourmet restaurants, and cultural landmarks, all within walking distance. The energy of the city flows through the hotel's elegant corridors, creating a backdrop for unforgettable experiences.

Romantic Break - With dreamy décor and intimate spaces, Hotel EMC2 is an idyllic retreat for couples seeking romance. Relish the culinary delights at The Albert Tavern, where seasonal dishes are paired with crafted cocktails that set the mood for evenings filled with connection and laughter.

Spa breaks - Recharge your senses in a haven of tranquility right in the bustling city. Enjoy wellness amenities designed to help you unwind, along with personalized services that cater to your every need, ensuring a rejuvenating escape from the urban rush.

Guest Experiences - Picture this: stepping into your room and being enveloped by the inviting aroma of freshly brewed coffee from your very own machine, while the natural light dances across the hardwood floors. A warm greeting from the front desk staff or an unexpected hot chocolate available in the lobby can make you feel right at home, as you prepare to explore the vibrant city just outside your door.

Nestled in the heart of Milwaukee, Hotel Metro, Autograph Collection offers a chic retreat where modern elegance meets historic charm. With its rich textures and inviting ambiance, this boutique hotel beckons couples, adventurers, and cultural explorers to unwind in style, creating unforgettable memories amidst the vibrant pulse of the city.

Romantic Break - Surrounded by stunning local art and the soft hum of laughter, every corner of Hotel Metro invites romantic escapades; from intimate dinners at the restaurant to cozy evenings on the terrace under twinkling lights.

City Style - With its sophisticated design and prime location, Hotel Metro serves as a stylish launchpad for urban exploration, making nearby cultural hotspots like Pabst Theater and Grohmann Museum easily accessible for curious guests eager to dive into the local scene.

Spa breaks - Indulge in moments of pure tranquility with their wellness offerings, where soothing aromas fill the air and gentle music whispers relaxation as you leave your cares behind in the serene atmosphere of the spa.

Guest Experiences - As I stepped into my spacious room, a luxurious scent of fresh linens enveloped me, complemented by the soft glow of elegant lamps that set the perfect mood. The staff, always attentive yet unobtrusive, made me feel cherished, ensuring every need was met even before I knew it was there.

Nestled in the heart of Milwaukee, The Iron Horse Hotel stands as a captivating fusion of history and contemporary elegance. This luxurious boutique gem, a lovingly restored 100-year-old warehouse, invites you to immerse yourself in a world where every corner tells a story, and every detail is meticulously curated for an unforgettable stay.

Romantic Break - Indulge in an intimate escape with your partner, surrounded by chic decor and a warm ambiance that whispers romance. The soft glow of vintage-inspired lighting creates an inviting atmosphere, perfect for lingering over a candlelit dinner at Ash Restaurant or sharing a signature cocktail at the BRANDED Bar.

City Style - Step outside your door and find yourself within walking distance of vibrant local attractions, from the iconic Harley-Davidson Museum to eclectic shops and lively restaurants. The hotel's location provides effortless access to the city's heartbeat, making it an ideal base for cultural explorers and adventure seekers alike.

Spa breaks - Unwind with tailored wellness offerings that beckon relaxation and rejuvenation. From soothing treatments to a cozy retreat atmosphere, every element is designed with your peace in mind, allowing you to disconnect and pamper yourself amidst the bustling city.

Guest Experiences - As you settle into your beautifully appointed room, take note of the custom hooks for your heavy leathers, a thoughtful touch that speaks to the hotel’s character. Imagine sipping coffee in bed while savoring the delightful aroma of freshly prepared breakfast wafting through the air, a friendly staff member ensuring everything is just right for your perfect morning.

Nestled in the heart of Chicago, just a whisper away from the iconic Water Tower Park and vibrant Michigan Avenue, the reimagined Park Hyatt Chicago transcends the ordinary, offering an elegant retreat for discerning travelers. Here, the energy of the city converges with moments of tranquility, creating a luxurious home away from home where every detail is curated for comfort and sophistication.

Outstanding Location - With its prime address, guests are perfectly positioned to explore the dynamic streets of Chicago, from designer boutiques to stunning cultural enclaves, all within walking distance. The gentle hum of the city outside serves as a vibrant backdrop to your stay.

Total Relaxation - Embrace serenity in the thoughtfully designed spaces that feature calming tones and plush furnishings, allowing you to unwind after a day of exploration. Each suite invites you to sink into the lavish bedding, where the soft whispers of Lake Michigan can be heard, lulling you into a peaceful slumber.

Spa Breaks - Indulge in a rejuvenating escape at the hotel's spa-like amenities, including a tranquil indoor pool that beckons with sparkling waters. Upgraded wellness facilities ensure your body and mind are as pampered as your spirit, providing the ultimate sanctuary amidst the urban bustle.

Guest Experiences - As the sun dipped below the skyline, one guest recalled savoring a casual breakfast while breathing in the rich aroma of freshly brewed coffee wafting from the restaurant. They marveled at how the staff's warm smiles made them feel like cherished family, even when their table was momentarily hard to secure.

Nestled amidst Chicago’s architectural marvels, Trump International Hotel & Tower Chicago offers a symphony of luxury, elegance, and panoramic beauty. With floor-to-ceiling windows framing breathtaking views of Lake Michigan and the bustling city skyline, each moment spent in this towering sanctuary is wrapped in an intimate embrace of sophistication and tranquility.

Outstanding Location - Perfectly situated just steps from the vibrant energy of Michigan Avenue’s Magnificent Mile, this hotel invites guests to explore upscale shopping, gourmet dining, and lively cultural attractions right at their doorstep.

Romantic Retreat - With its plush furnishings and serene atmosphere, the hotel becomes a haven for couples, where candlelit dinners on the seasonal terrace provide the backdrop for unforgettable moments against the stunning skyline.

Spa & Relaxation - Indulge in rejuvenating spa services that blend tranquility with indulgence, offering treatments that awaken the senses while enveloping you in the soothing ambiance of this luxurious oasis.

Guest Experiences - Guests have remarked on the delightful attentiveness of the staff, who seem to anticipate needs before they arise—whether it’s a warm greeting or a perfectly poured cocktail—with the inviting aroma of fresh sushi wafting through the air at Rebar, setting the stage for a truly memorable evening.

Nestled in the heart of Chicago, Loews Chicago Hotel beckons with an alluring blend of modern luxury and urban charm. Here, every moment is infused with romance, from the breathtaking skyline views enjoyed at the rooftop lounge to the warmth of the lobby fireplace, where guests can unwind with a glass of wine after a day of exploring the vibrant city.

Romantic Retreat - Every corner of Loews Chicago whispers romance, whether it's the softly lit ambiance of the on-site restaurant or the intimate seating at the rooftop bar overlooking twinkling city lights, perfect for couples seeking a memorable escape.

Outstanding Location - Just steps away from the Chicago River and within walking distance of Millennium Park and Navy Pier, the hotel offers easy access to the city's best attractions while providing a serene oasis to return to after a day of discovery.

Spa Breaks - Indulge your senses in the hotel's state-of-the-art fitness center or take a dip in the expansive indoor lap pool, where gentle water ripples echo the tranquility of a spa retreat, allowing guests to rejuvenate body and spirit without leaving the premises.

Guest Experiences - As I entered the lobby, the rich aroma of freshly brewed coffee greeted me, mingling with the soft sounds of holiday carolers creating a cozy atmosphere that instantly felt like home. My room was a haven of comfort, with plush bedding inviting me to sink in, while the spacious bathroom offered a luxurious touch, making even simple routines feel indulgent.

Nestled just steps away from the pulsing energy of Chicago's Magnificent Mile, Sofitel Chicago Magnificent Mile offers a sanctuary of elegance and comfort. With its stunning prism glass façade reflecting the shimmering skyline and tranquil Lake Michigan, this luxurious hotel invites you to indulge in an experience where French sophistication meets Midwestern warmth.

Romantic Break - Experience romance like never before in intimate settings adorned with chic French art de vivre decor, plush beds enveloped in feathertop duvets, and views that inspire stolen kisses against the city skyline.

Outstanding Location - Flanked by the vibrant energy of shopping and dining, yet nestled in a peaceful oasis, this location allows for easy adventures — whether it's a leisurely stroll to the Art Institute or a caffeine fix at local cafés just around the corner.

Total Relaxation - Unwind in spacious marble bathrooms complete with luxurious amenities, or enjoy crafted cocktails with panoramic views at Le Bar, where the city's heartbeat is matched only by the gentle clink of glasses celebrating life's finest moments.

Guest Experiences - As I stepped into the lobby, the delightful aroma of fresh coffee mingled with the festive scent of pine from the holiday decorations. The bellhop, eager to assist and genuine in his kindness, made my arrival feel like a warm embrace, creating a memorable first impression that lingered throughout my stay.

Nestled along the serene banks of the Chicago River, L7 Chicago by LOTTE exudes a chic sophistication that makes it an enchanting retreat in the heart of the bustling Loop. With its contemporary design and lavish amenities, every moment is steeped in luxury—whether you're unwinding after an adventurous day or indulging in intimate evenings with stunning city views as your backdrop.

Outstanding Location - Experience the vibrancy of Chicago with effortless access to iconic landmarks like Millennium Park and the Magnificent Mile, all just a leisurely stroll away. The pulsating energy of the Theater District beckons, ensuring that every night holds the promise of unforgettable performances.

Spa & Relaxation - Unwind in your stylish sanctuary, complete with plush bathrobes and yoga mats, inviting you to indulge in moments of tranquility. Personalized in-room spa services allow you to melt away the day’s stresses, letting you bask in relaxation without ever leaving your private oasis.

City Style - Step into a world where modern aesthetics meet urban charm, characterized by designer touches throughout the hotel. Each room, equipped with a 55-inch LCD TV and luxurious bedding, welcomes you with a fresh, invigorating ambiance that feels both homey and upscale—perfect for those seeking both comfort and elegance.

Guest Experiences - As the aroma of freshly brewed coffee wafts through the lobby, friendly staff greet you with genuine warmth, making you feel not just welcomed but truly special. A guest was particularly enamored by the doorman's lively spirit; his cheerful banter and engaging personality set the tone for their entire stay, creating an atmosphere that felt akin to visiting an old friend.

Nestled in the vibrant heart of Chicago, Virgin Hotels Chicago redefines urban luxury with its chic design and thoughtful amenities. Just steps from the bustling Magnificent Mile, this boutique hotel invites you to experience modern comfort intertwined with playful elegance, making it an enticing escape for couples and cultural explorers alike.

Romantic Retreat - With spacious rooms designed for relaxation, couples can unwind in a tranquil sanctuary featuring plush bedding and elegant décor. The unique dressing area enhances privacy, allowing moments of intimacy as you prepare for a night out amidst the city's twinkling lights.

Culinary Delights - Savor the essence of Italy at Miss Ricky's, where the aroma of freshly baked pastries wafts through the air, inviting you to indulge in delightful meals served throughout the day. Enjoy al fresco dining with panoramic views that transform each meal into a memorable experience.

Vibrant Atmosphere - The rooftop bar is a lively haven, where the rhythmic sounds of laughter blend with city life, creating an electric ambiance perfect for mingling or unwinding. Sip craft cocktails while soaking in breathtaking skyline vistas that elevate any evening.

Guest Experiences - As you stroll through the hotel, catch a whiff of refreshing flavored water near the lifts, a small but thoughtful touch that adds to the warmth of your stay. Guests have noted how the friendly staff often go the extra mile, sharing tips on hidden gems nearby while offering a cozy smile.

Nestled in the vibrant heart of Rosemont, just steps away from the bustling Fashion Outlets of Chicago, Loews Chicago O'Hare Hotel invites you into a world of sophisticated charm and modern luxury. With its sleek stone finishes and plush bedding, this contemporary retreat is designed for both indulgence and relaxation, perfectly tailored for couples seeking romance or business travelers in need of convenience.

Exceptional Dining - Savor an exquisite culinary journey at the aviation-themed Ashburn Restaurant, where classic American gastropub fare meets an innovative twist, or indulge in dry-aged steaks at The Capital Grille. Each meal is crafted with care, ensuring that whether you're dining solo or with friends, every bite resonates with flavor and intention.

Artful Surroundings - Immerse yourself in the creativity of local artists showcased in the on-site Art/Museo gallery, offering a refreshing backdrop to your stay. The rotating exhibits whisper stories of community and culture, enveloping guests in an experience that lingers long after the visit.

Unmatched Comfort - Retreat to your spa-inspired room adorned with soft textures and calming hues, where the 42-inch flat-screen TV and ergonomic workspace invite both relaxation and productivity. The bedding cradles you like a gentle embrace after a day spent exploring the vibrant surroundings or attending events at the nearby convention center.

Guest Experiences - Imagine stepping into a world where the scent of freshly prepared seafood wafts from McCormick and Schmick's, while the warm smiles of staff greet you at every corner, creating a welcoming oasis. One guest marveled at the extra attention they received from shuttle drivers, who went out of their way to ensure accessibility and comfort, turning travel into a seamless joy.

Nestled in the vibrant heart of Chicago's Loop, the Silversmith Hotel presents a harmonious blend of historic elegance and modern luxury. With its contemporary design and intimate ambiance, this boutique gem invites couples and romance-seekers to immerse themselves in a city pulsating with culture, art, and culinary delights.

Romantic Break - Elevate your getaway with luxurious accommodations that envelop you in warmth and sophistication, featuring plush bedding and spacious layouts designed for intimate moments.

Outstanding Location - Steps from iconic attractions like Millennium Park, you'll find yourself surrounded by the city's artistic heartbeat, with lively streets filled with the aroma of gourmet eateries and the buzz of local markets.

Spa & Relaxation - Unwind in the comfort of your room, where every detail invites relaxation, from the soothing scents of fresh coffee brewing in your own coffeemaker to the plush textures of finely curated furnishings.

Guest Experiences - Imagine savoring a handcrafted cocktail in the chic Adamus Lounge, the faint clinking of glasses mingling with the soft hum of conversation, while a friendly staff member shares local secrets about hidden gems just around the corner.

Nestled in the vibrant Wicker Park neighborhood, The Robey, Chicago seamlessly blends historic charm with contemporary elegance. As you enter, the air is tinged with the rich aroma of freshly brewed coffee from Café Robey, beckoning you to indulge in a culinary journey while basking in the chic ambiance that surrounds you.

City Style - Experience the heartbeat of Chicago from a prime location where hip boutiques mingle with eclectic eateries, all just steps from your door. Each light-filled room invites you to unwind with hardwood floors and luxurious 400-thread count sheets, creating an oasis amidst the city's lively backdrop.

Rooftop Retreats - Ascend to The Up Room on the 13th floor for a cocktail experience unlike any other, where panoramic views of the skyline create a picturesque setting for evening gatherings. In summer, escape to Solana, a hidden rooftop oasis that offers lush seating and refreshing drinks, perfect for lazy afternoons under the sun.

Culinary Delights - From savoring New American fare at the café to sipping nostalgia-laden cocktails at Clever Coyote, the hotel's dining scene is a feast for the senses. Guests rave about the thoughtful menu options, nestled within warm, inviting spaces designed to foster connection and conversation.

Guest Experiences - One guest couldn’t help but smile as they found their favorite umbrella tucked neatly away in the room—an unexpected touch that spoke volumes about The Robey's attention to detail. The mesmerizing view from their sixth-floor window provided endless distraction, transforming ordinary moments into extraordinary memories.

Nestled in the heart of Chicago's prestigious Gold Coast, Waldorf Astoria Chicago beckons with an air of timeless elegance and intimate luxury. As you enter through the enchanting private courtyard, a sense of tranquility envelops you, reminiscent of a French château where every detail whispers sophistication and romance.

Total Relaxation - Indulge in unparalleled serenity at the on-site spa, where the soothing aroma of essential oils wafts through the air as expert therapists guide you to blissful rejuvenation. A dip in the serene indoor pool invites you to unwind beneath the soft glow of ambient lighting, creating a sanctuary for relaxation.

Romantic Break - Every corner of this exquisite hotel is designed for romance; imagine cozying up by your fireplace in the elegantly appointed suite, or savoring a candlelit dinner at The Brass Tack, where each dish bursts with flavors that tantalize the palate, leaving you longing for just one more bite.

Spa Breaks - With a focus on wellness, the well-equipped fitness center hums softly, inviting guests to maintain their routines while traveling. After a workout, retreat to the spa’s tranquil zone, where calming sounds and plush textures cradle you into a state of total peace, a perfect prelude to a pampering treatment.

Guest Experiences - Guests frequently reminisce about the breathtaking views from their rooms, where the city skyline dazzles like a jewel, complemented by the crackling warmth of the fireplace that creates an intimate ambiance for a cozy night in. One guest even noted the delightful scent of fresh linens that filled their room, enhancing the overall feeling of comfort and indulgence.

Nestled within a beautifully restored 19th-century gem, the Chicago Athletic Association, part of Hyatt, invites you to indulge in an ambiance where history meets modern luxury. Picture yourself sipping a craft cocktail on the rooftop terrace, with breathtaking views of Millennium Park and Lake Michigan, as the vibrant energy of downtown Chicago pulses just below your feet.

Historic Charm - Step into a world where vintage elegance coexists with contemporary flair; the hotel's stunning architecture features intricate stained glass and rich wood, setting the perfect backdrop for romantic getaways or inspiring business retreats.

Gastronomic Delights - Savor a culinary journey at Cindy's, where seasonal dishes dance harmoniously with handcrafted cocktails, all while you relax on the open-air terrace, enveloped by a gentle breeze and captivating city views.

Engaging Entertainment - Unleash your competitive spirit in the lively games room, complete with antique billiard tables and shuffleboard, where laughter fills the air, and the warm glow from the fireplaces invites cozy conversation long into the evening.

Guest Experiences - Imagine being greeted by a friendly staff member who personally escorts you through the grand lobby, where the inviting scent of freshly brewed coffee wafts through the air, complemented by the nostalgic sound of games being played just beyond the plush seating.

Nestled in the vibrant heart of downtown Chicago, Ivy Boutique Hotel offers a sanctuary where luxury intertwines with urban charm. With its modern design and intimate ambiance, this chic retreat is perfect for couples seeking romance or solo travelers desiring a tranquil escape amid the city's bustling energy.

Romantic Break - Experience enchanting evenings overlooking the city skyline from the outdoor Sky Terrace, where the soft glow of sunset casts a warm hue over signature cocktails and delectable appetizers, inviting you to create memories that linger long after your stay.

Total Relaxation - Unwind in spacious rooms adorned with dark wood decor and plush furnishings, where automatic window drapes allow for effortless privacy and the temptation of spa services beckons for indulgent pampering amidst the city’s pulse.

Outstanding Location - Just two blocks from the renowned Magnificent Mile, the hotel places you within easy reach of eclectic dining options and cultural gems, making every exploration feel like a delightful adventure waiting just outside your doorstep.

Guest Experiences - Guests rave about the delightful surprise of spacious suites, where sunlight floods through floor-to-ceiling windows, creating an inviting atmosphere that feels like home, complemented by friendly staff who are always ready with coffee recommendations from nearby artisan cafés.

Nestled in the heart of Chicago's vibrant Loop, Kimpton Gray Hotel is an exquisite blend of modern elegance and rich history, inviting couples and explorers alike to unwind in a haven of luxury. Here, amidst the sounds of the city and the aroma of gourmet delights wafting from Boleo, you’ll find a perfect sanctuary that effortlessly balances sophistication with warmth.

Romantic Retreat - With chic décor and plush furnishings, each room transforms into a romantic escape, complete with lavish Atelier Bloem bath products and cozy robes waiting to envelop you after a day of urban adventures.

Culinary Delights - At Boleo, indulge in Latin-inspired cuisine paired with stunning rooftop views that stretch across the Chicago skyline, igniting your senses as the sun sets and the city lights flicker to life.

Central Location & Local Exploration - Just steps from the iconic Magnificent Mile and a quick stroll to cultural treasures like Grant Park and the Art Institute, this hotel serves as your gateway to the city's most celebrated sights and hidden gems.

Guest Experiences - Guests have marveled at the delightful surprise of an upgrade upon arrival, finding themselves in immaculate rooms where everything—from the sparkling clean furnishings to the delightfully attentive staff—creates a soothing atmosphere, making it feel like a cherished home away from home.

Nestled in the vibrant heart of Chicago, The Hotel & Athletic Club at Midtown offers a sanctuary where luxury meets wellness in an elegant and modern setting. With its exquisite amenities and a serene atmosphere, this upscale retreat is designed for those seeking both relaxation and rejuvenation, inviting you to indulge in a world of comfort and sophistication.

Total Relaxation - Unwind in an oasis of tranquility with access to pristine indoor and outdoor lap pools, soothing whirlpools, and a spa that envelops you in a calming ambiance. The gentle scent of eucalyptus wafts through as you surrender to blissful treatments after a day filled with adventure.

Active Holiday - Engage your body and spirit with state-of-the-art workout facilities and over 190 group fitness classes available weekly, from invigorating yoga sessions to high-energy boxing workouts. Feel the pulse of vitality as expert trainers guide you on your journey toward peak wellness.

City Style - Located just minutes from iconic attractions like Wrigley Field and Lincoln Park Zoo, embrace the chic urban vibe as you explore bustling local markets or savor culinary delights at nearby restaurants. Each outing promises a blend of culture and excitement that enchants adventurers and casual explorers alike.

Guest Experiences - As you step into the gym, the fresh scent of clean equipment fills the air, while friendly trainers engage you with genuine smiles and thoughtful gestures, like a warm eucalyptus towel after a rigorous session. Cozy beds wrapped in soft linens invite you to sink in after a long day, making it feel like home away from home.

Nestled within the grandeur of a historic French Beaux-Arts building, The Blackstone, Autograph Collection invites you to experience a romantic retreat where Chicago's vibrant energy meets timeless elegance. As you step into the beautifully adorned lobby, the rich aromas from the Catalan-inspired restaurant mingle with the soft sounds of laughter and conversation, creating an atmosphere steeped in warmth and sophistication.

Historic Charm - Every corner of The Blackstone tells a story—from its architecturally stunning façade to the intricately designed interiors that whisk you back to a bygone era. This is more than just a hotel; it's a sanctuary filled with character and romance, perfect for couples seeking a memorable escape.

Culinary Delights - Savor the flavors of the Mediterranean at Mercat a la Planxa, where each dish bursts with authenticity and creativity. Picture yourself sharing tapas amid the whispers of intimate conversations, the clinking of glasses, and the tantalizing scent of spices wafting through the air.

Unparalleled Location - Situated right across from Grant Park and just a stone's throw from the Art Institute and Millennium Park, The Blackstone offers unparalleled access to Chicago's cultural treasures. Stroll through lush green spaces or lose yourself in artful delights—each moment is effortlessly yours to savor.

Guest Experiences - As guests unwind in their impeccably clean rooms, many have remarked on the delightful surprise of waking up to breathtaking views of Lake Michigan, while the gentle rustle of leaves from nearby Grant Park creates a soothing background melody. One guest even shared how the attentive manager turned a reservation hiccup into a personal touch, showcasing the hotel’s commitment to exceptional service.

Nestled in the heart of Chicago's vibrant Theater District, the Renaissance Chicago Downtown Hotel is an urban oasis where modern luxury meets artistic inspiration. With stunning views of the iconic skyline and the serene Chicago River, each moment here invites you to unwind, explore, and indulge in the chic energy that pulses through the city streets.

Outstanding Location - Just a leisurely stroll away from world-class dining and entertainment, the hotel positions you at the center of it all—a perfect launchpad for your Chicago adventures, whether you're savoring a gourmet meal or soaking in a riveting theater performance.

Romantic Break - With sleek, contemporary décor and sumptuous amenities, every corner whispers romance—perfect for couples seeking a getaway filled with intimate moments and breathtaking cityscapes.

Spa Breaks - Refresh and recharge in the indoor pool, where the soft sound of water lapping against the sides creates a serene escape from the bustling city outside, complemented by thoughtful touches that enhance your wellness journey.

Guest Experiences - As you sink into your plush room, the tantalizing aroma of a fresh brew from the coffee bar wafts through the air, mingling with the lively sounds of the city below. Guests often mention how the glow of the sunset over the river transforms their view into a vibrant canvas of colors, crafting unforgettable memories.

Nestled in the heart of Milwaukee's historic Third Ward, the Kimpton Journeyman Hotel invites you to embark on a sensorial journey where modern elegance intertwines with local charm. Imagine sipping craft cocktails at sunset while the city skyline glows around you, all from the comfort of our enchanting rooftop bar—a perfect backdrop for romance or quiet reflection.

Outstanding Location - With its prime position, you're just steps away from vibrant art galleries, eclectic shops, and the serene shores of Lake Michigan, making exploration effortless and delightful.

Chic Rooftop Bar - Elevate your evenings at our rooftop oasis, where the air is filled with laughter and clinking glasses as you enjoy panoramic views that dance between the city lights and the setting sun.

Romantic Retreat - Every room is a cozy haven, adorned with unique artwork and plush furnishings, providing an intimate escape that's perfect for lovebirds and solo sojourners alike.

Guest Experiences - Guests have relished unexpected touches like the delightful surprise awaiting them on their anniversary—perhaps a sweet treat in the room—or the exhilarating moment of discovering a mini-fridge stocked with local delights. The inviting scents of freshly brewed coffee waft through the lobby each morning, beckoning you to start the day with a smile.