Despite being one of the largest cities in the US, the windy city makes a fantastic destination for an intimate romantic couple’s break. Take a scenic bike ride along Chicago’s lakefront, people-watch from a cafe patio in Lincoln Square, take a loved up stroll in Millennium Park, check out a top art exhibition or theatre performance, dine out at an acclaimed restaurant and then enjoy a cocktail coupled with sweeping city views from a rooftop bar for a perfect romantic break for two. Of course, you’ll want to stay someone equally as captivating. So from sexy and sleek suites to cozy and intimate hotels here is our collection of the most romantic hotels in Chicago chosen so they will impress that special someone…
Villa D’Citta – a romantic and elegant B&B housed in a Tuscan-style villa that dates from 1897
This intimate and romantic four-star B&B is housed in a beautiful Tuscan-style villa that dates from 1897 and is nestled in leafy streets, just moments away from the heart of Chicago’s Lincoln Park. With beautiful decor and an intimate character, reflecting its past life as a tycoon’s ‘pied-a-terre,’ it’s the perfect dreamy cosmopolitan weekend retreat. Whether you want to explore the city or snuggle in your sumptuous room, you won’t be disappointed.
All rooms at the romantic Villa provide the best in entertainment with widescreen TV and High-Speed Wi-Fi as standard. The rooms at Villa D’Citta compliment’s this with a gourmet kitchen, on-site theatre, and secluded sun deck with jacuzzi. With its friendly and attentive staff, consistently excellent TripAdvisor reviews, this sumptuous and ultra-romantic Chicago hotel seemingly made for couples is a must.
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Thompson Chicago – a sleek and sexy hotel set among the mansions of Chicago’s Gold Coast which is perfect for couples in love
This chic and romantic four-star hotel has been carefully curated and designed by British designer Tara Bernerd and is perfect for romantic getaways in the Windy City. It’s a stylish blend of relaxing rusts and ambers combined with an urban aesthetic, make it an ideal couple’s retreat. Located near Michigan Avenue and The Magnificent Mile, close to Lake Michigan, you can almost touch the beating heart of the city.
The Thompson Chicago offers sophisticated dining at Nico Osteria Italian seafood restaurant as well as a relaxing cocktail lounge. The stylishness continues into your room where your king bed is dressed in Sferra linens, and your bathroom is equipped with a rain shower. Control your comfort with adjustable aircon while watching TV or using Wi-Fi. Its friendly, helpful staff complete the romantic package.
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Ambassador Chicago – a romantic hotel housed in the historic Ambassador East Hotel which has roots in Chicago’s Jazz Age
History shimmers on entering the four-star Chicago Ambassador, reminding you it’s not just a name. Your romantic city break is immediately electrified by the vaulted ceilings enclosing the intimate décor of the lobby below. The Windy City is a haven for sexy, sophisticated fun, with the Magnificent Mile and the iconic Water Tower Place within touching distance.
The Ambassador’s rooms reflect the chic ambiance of the city with tasteful décor, mini bar, air conditioning, Wi-Fi, and Widescreen TV. The hotel’s friendly, attentive staff will help you enjoy experiences from world-class dining to free bicycle rental. With consistently high TripAdvisor ratings, you know this glamorous and romantic trip will set hearts racing.
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Waldorf Astoria Chicago – the premier luxury hotel in downtown Chicago which is perfect for a romantic city break
The Waldorf Astoria is renowned for five-star luxury and service. With a location in the heart of the city, it is the perfect base for your romantic break. With their Concierge Ambassador directing you to all the best attractions, you can concentrate on enjoying your time together. The sumptuous deluxe rooms are large and airy, with intimate seating in front of a real fireplace. The romantic rooms at Waldorf Astoria Chicago also offer Wi-Fi and flat-screen TVs.
This opulent hotel boasts a spa, swimming pool, and a health club. After being pampered, why not enjoy the in-house, world-class dining experiences. With warm, professional staff to enhance your romantic break, it’s no surprise they are highly rated on TripAdvisor.
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The Peninsula Chicago – an upscale Chicago hotel set in a landmark high-rise guaranteed to impress your loved one
The Peninsula hotel is an artful blend of Eastern and American hospitality, earning a Forbes Five-Star rating every year since opening. The Peninsulas’ location close to the Magnificent Mile and Lake Michigan makes it ideal for couples planning a romantic break. The blended chic of the Eastern and American aesthetics makes the rooms at subtle and calm, yet still visually engaging.
The beds and furnishings are comfortably opulent in a low-key way, and all rooms at the Peninsula Chicago offer air conditioning, Wi-Fi, and a widescreen TV for a comfortable, cosseting stay. Beyond your chic and romantic room, the terrace and rooftop bars provide great food, a relaxing ambiance, and the unforgettable views needed for an intimate break for two.
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A stunning romantic hotel in the best neighborhood of Chicago, Nobu Hotel Chicago is nestled in the heart of West Loop. Combining the spirit of vibrant Randolph Street with amazing views of the city, each stay at the hotel is a Zen retreat.
The playful elements of old-world Japanese art, tall ceilings, and minimalist-style rooms bring out the true essence of Nobu with its welcoming services. Enjoy the scene at the Rooftop with the best views of Chicago’s skyline or take advantage of the in-room dining; you can experience the Windy city’s culinary hubs steps away.
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The Publishing House – a stylish and intimate hotel set in a former publishing house on a tree-lined street
Part B&B, all boutique hotels, the Publishing House is a book waiting to be opened. With a great central metro location, all the Windy City’s delights are easily accessible for a fun-loving couple escaping the grind. With 11 uniquely designed cozy and intimate rooms, you and your partner will feel pampered, entertained, and invigorated. Its diminutive size adds to the sense of intimacy and exclusivity, which larger hotels can struggle to create.
The hotel’s décor throughout is a low key, light touch, funky chic, and the friendly staff are able to devote more time to your needs, making it easy to believe the hotel has been laid on especially for you. The Publishing House consistently scores full marks on TripAdvisor so enjoy your romantic Chicago stay!
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The Gwen Chicago – an upscale contemporary hotel with fabulous views perfect for a chic and romantic city break
When you think of Great Lakes luxury and Chicago chic, the four-star Gwen on the Magnificent Mile has it all. Not only do you have access to Chicago’s splendid attractions, but you’re also staying in one! In terms of romantic, sumptuous surroundings, The Gwen Hotel hits the spot.
The décor through the main space is pure 1930’s Chicago sophistication, and the romantic guest rooms live up to the billing too with classic 1930’s styling, indulgent Frette linen, and oversized showers. Contemporary needs are catered for with Wi-Fi and widescreen TV. With world-class dining facilities and cozy terraced bars, the Gwen is perfect for romantic getaways. With friendly staff to enhance your stay, their high ratings on TripAdvisor are well deserved.
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The Langham Chicago – a stylish and romantic hotel set in a Mies van der Rohe landmark tower and offers sweeping views of Lake Michigan
The Langham Hotel is frequently rated as one of the world’s top hotels and is an artful blend of Chicago and London styling, wrapped up in one five-star package. Located just a hand-in-hand stroll from the Magnificent Mile, it’s perfect for getting surprise gifts or theatre trips on your intimate and romantic city break. The guest rooms are airy and elegantly decorated and primed for romance.
Most provide cityscape views that are wonderful by day and even more stunning by night. With an award-winning spa, gym, and pool, you can stay in shape between luxurious meals available in-house. The abundance of friendly, professional staff means it’s no surprise they have thousands of top ratings on TripAdvisor.
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The Ritz-Carlton Chicago – arguably the most iconic place to stay in the city so perfect for an extra special romantic break
‘Putting On The Ritz’ is an anthem for all things opulent, and the Ritz-Carlton Chicago lives up to its five-star name and so much more. Set in Chicago’s Gold Coast district, you have easy access to historical and contemporary attractions alike. The hotel’s interior reflects the city outside with sophisticated décor and an enviable art collection.
The romantic rooms, floating high over the city, frame both the cityscapes and Lake Michigan perfectly. They are subtly decorated and sumptuously appointed. Twice daily housekeeping ensures your romantic sanctuary is always perfect and ready to receive you. There is Wi-Fi and a safe for your valuables too. Beyond your room, indulge yourselves in haute cuisine, or intimate drinks in the bar. Treat yourself and your loved one at this highly-rated Chicago staple.
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The Viceroy Chicago – a sophisticated Art-Deco inspired hotel located in the Gold Coast Historic District
This impressive five-star hotel is located in the Gold Coast neighborhood. Poised at the heart of the city, The Viceroy Hotel is primed for adventure, culture, and nightlife. Upon returning, luxuriate in beautifully appointed, well-specified rooms perfect for a chic and romantic Chicago break.
With 24-hour room service, luxurious beds, and amenities including TV and Wi-Fi, your romantic break will be just perfect. Beyond your room, enjoy the roof deck pool together, get pampered with a massage at the spa, or visit the fitness center. Alternatively, book the in-house restaurants for fine American dining. Whatever you and your loved one choose to do, it will be relaxing, memorable and hopefully very romantic!
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Sophy Hyde Park – a sophisticated and artistic boutique hotel for an idyllic romantic city break
Embodying the spirit of Hyde Park’s creativity and music, Sophy Hyde Park is located in the city center near the boardwalk. Immerse yourself in the colorful artwork and hardwood floor sitting area the moment you enter the lobby. Added to the vibrant and modern rooms with oversized art, flat-screen TV, kitchen, and soaking tub, exceptional hospitality makes Sophy Hyde warm, inviting, and perfect for a stylish romantic break in Chicago.
Beyond your room, splurge your loved ones in an on-site restaurant with culinary classics. A short drive from downtown Chicago, the boutique hotel is surrounded by countless shops, restaurants, and entertainment destinations.
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The Godfrey Hotel Chicago- an upscale hotel in the vibrant River North neighborhood perfect for a stylish couple’s romantic break
The Godfrey Hotels Cubist architecture oozes modernity, while its boutique ethos provides a personalized ambiance, making this four-star hotel perfect for romantic breaks. Its location in the heart of Chicago lets couples easily explore the attractions of the Windy City. The guest rooms at the Godfrey Hotel are comfortable and well equipped.
The bedding uses fine, comfortable textiles, complimenting the other furniture and the 46″ TV and Wi-Fi takes care of modern communications when needed. The presence of a hairdryer and L’OCCITANE bathing products enhances the package further. Beyond your romantic room, the IO Rooftop Lounge provides relaxing surrounds to share a glass of champagne with your partner.
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The Hotel Zachary Chicago – a chic and romantic boutique hotel next door to Wrigley Field
The Zachary is located next door to Wrigley Field, home of the world-famous Chicago Cubs on the North Side, yet the location is still just minutes from downtown. For a lighter feeling romantic weekend, the Zachary Hotel is perfect. From here, you have easy access to all of the shopping experiences, romantic restaurants and live entertainment venues situated in the heart of Chicago.
The rooms are airy, modern, and well designed with lots of utilities to make your stay a breeze. There are hairdryers, a writing desk, and a safe for your valuables. Of course, communications are covered by free Wi-Fi and a widescreen TV. If you want, you can book a room overlooking the Cubs stadium to soak up the atmosphere on game night with the one you love. The hotel also provided 24-7 access to a well-equipped gym, in case all the sporting action inspires you to get your pulse racing.
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EMC2 Chicago – a sleek and stylish hotel located in the Magnificent Mile shopping district
The EMC2 Hotel offers a fun, quirky stay for the eternally curious. Named after Einstein’s famous equation and designed to blend creativity and logic, art, and science, it provides an experience ideal for a playful romantic getaway. Located inside Chicago’s lively Streetsville neighborhood in the Magnificent Mile, the EMC2 provides easy access to the city’s attractions.
Fine dining perfect for romance is available at the onsite Albert restaurant, which offers yet another homage to the great man himself. The engaging quirkiness extends to your room too. The rooms are comfortable, modern and elegant. They come with TV, Wi-Fi, fridges and hot drinks facilities. You may even get room service from a robot waiter! The friendly staff are here to complete the experience and guarantee a fun, relaxing and hopefully very romantic stay.
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The Blackstone – an ornate and romantic Chicago hotel housed in a 1910 beaux-arts building
The iconic Blackstone is a romantic four-star hotel that provides the amenities of a modern luxury hotel with the sexy glamour of a boutique establishment. The Blackstone Hotel‘s convenient location eases you into the theatre district, and Millennium Park makes for enjoying intimate evenings together.
Enjoy each other’s company with the cuisine of Catalonia at Mercat A La Planxa, and to balance the indulgence, the state-of-the-art gym overlooks the lake. Rooms are elegant, stylish, and romantic with guests having the option to book one overlooking Lake Michigan itself. The professional and attentive staff are always on hand to enhance your stay and make it special.
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Kimpton Gray Hotel Chicago, an IHG Hotel – an upscale romantic hotel with sophisticated charm for couples in love
Set in one of the finest landmarks of Chicago, the historical building of the Kimpton Gray Hotel is located at the center of the Loop in downtown Chicago. The ornate marble designs and contemporary-style guest rooms with crisp furnishings make the property a fine example of a modern luxe hotel. Filled with unique décor, spacious rooms and a private bathroom with a tub, Kimpton Gray is a cozy abode for couples in love.
Laze away in the vintage bathtub, enjoy the complimentary evening cocktail or relish the Latin-inspired cuisine at the rooftop Boleo restaurant, an extraordinary experience awaits at the Kimpton Gray Hotel. With easy access to the city’s top attractions, the plush hotel makes for a mini-vacation in the city.
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Claridge House – an elegant and intimate hotel in the tiny haven of the Gold Coast
A beautiful and quaint property set on the affluent Gold Coast, Claridge House is a world away from Michigan Avenue’s bustle. Wake up in an authentic neighborhood with some of the best frames of the city, a stay at Claridge House will make you enjoy Chicago like a local. The chic guest rooms with modern amenities, including the spa-inspired bathroom & minibar, give a perfect retro yet modern vibe.
Excercise at the on-site fitness center or pamper your loved ones at the hotel spa, Claridge offers fabulous on-site dining with incredible services. The favorable location, just a short walk from Oak Street Beach & Magnificent Mile, makes for a blissful nest to take rest.
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The Palmer House Hilton – a plush and opulent hotel set in the theater and financial district a great option for a special couple’s break
Hilton hotels are known for quality, and the Palmer House Hilton is no exception. With 140 years of experience, your romantic break is in safe hands here. With opulent décor and outstanding facilities, including bars, restaurants, a health spa, and a gym, you may feel no need to leave your four-star accommodation during your stay.
But venture out you must, as this impressive hotel is in the heart of the Windy City, near Millennium Park, the Art Institute and theater district. The elegance of the hotel continues into the luxurious bedrooms where you and your loved one can expect a king bed, HDTV, free Wi-Fi. Additionally, a hairdryer and iron help you prepare for a romantic evening on the town.
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The Penthouse at Grand Plaza – a sexy and stylish penthouse with exceptional views for a private romantic break
Make yourself at home with the uber-stylish and spacious penthouses at the Penthouse at Grand Plaza. Located at the center of Chicago’s most exciting neighborhoods, the penthouse offers an unbeatable view of the lively Windy City.
From chic bedrooms, magnificent ceiling windows, private balcony to a full-equipped kitchen & dining, gorgeous décor & exquisite fireplaces, this unique rental property makes for a lovely time on the top with your loved ones.
Bordered by the elegance of North Michigan Avenue and River North District, the hotel offers a wide array of on-site amenities with sightseeing steps away.
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