Chicago is one of the largest cities in the U.S. It is popular for its eye-catching skyscrapers such as The Skydeck at Willis Tower and The Ledge. The Windy City, which sits on Lake Michigan, has also a lively culture and art scene, which attracts tourists from all around the globe.
To make your getaway more unique, here is a list of boutique hotels, inns, and holiday homes to stay in when you visit Chicago.
This luxury boutique hotel in Cook County features romantic rooms with large windows overlooking the city, soaking tubs in select units, as well as couples massages and other spa services.
There’s also a half-Olympic indoor pool boasting a stunning view of the city. Plenty of dining options are available in and around this pet-friendly property, as well.
If you would like to stay in a similar hotel that offers hot tub suites, check out this list of Chicago hotels with hot tubs in rooms.
Set in Chicago’s coolest neighborhood, West Loop, The Publishing House Bed and Breakfast makes for a fantastic romantic getaway.
The B&B features a shared lounge and spacious rooms with double beds, and seating area. It’s a quiet comfortable place where couples can have a relaxing weekend. This 110-year old building offers Chicago’s best bed and breakfast in a luxurious setting.
Buffet breakfast is also served in the hotel.
Great location, excellent services, and superb facilities, The Langham Chicago is a the perfect place to celebrate anniversaries. Some rooms have a spa tub and a view of the cityscape.
Guests can also relax and pamper themselves at the hotel’s on-site spa and massage facilities. A fully-equipped gym is also available.
Other amenities include an indoor pool, and indoor play area for kids and families.
Located in downtown Chicago, Hotel EMC2, is situated near the best attractions the city can offer. Featuring a romantic view of the cityscape, this pet-friendly hotel is ideal for couples. For more romantic hotels in Chicago, click here.
Each accommodation is equipped with TV, refrigerator, and coffeemaker, and a modern bathroom with glass enclosures while select rooms have large windows overlooking the city.
The Archive Lounge is a great place to hang out and have an evening cocktail.
Unwind and pamper yourself in one of the most romantic hotels in Chicago. Located in West Loop, this boutique hotel features luxurious hot tubs in select rooms.
Featuring cozy and high-end rooms with a romantic view of the cityscape – perfect for dates-, the hotel also features a spa facility, massage services, swimming pool, and fitness center.
Couples can enjoy their favorite cocktail drinks at the rooftop bar.
Set in Hyde Park, one of Chicago’s hip and sophisticated neighborhoods, guests of this boutique hotel can enjoy cycling, tennis, and live performances nearby.
The rooms are accentuated with vibrant furnishings and the lounge is visually appealing. Artworks are featured in every corner. Their deluxe king suite features a spa bath in addition to a private kitchen and TV.
Featuring homey hardwood-floor rooms with modern decors and amenities, this luxury hotel is an excellent choice. For more luxury options in Chicago, click here.
Located in downtown Chicago, the Ivy Boutique Hotel boasts high-end facilities and a rooftop bar that serves delicious cocktails. It’s also conveniently located close to many shops and bars.
A coffee machine, TV, and a minibar are included in every room. Guests can also sign up for free yoga classes.
Choose from spacious studios or the luxurious Queen and King Suites, which feature a seating room and an en-suite bathroom with a bathtub. Spa services are also offered with an additional fee.
This charming boutique hotel in Chicago offers amenities that couples and families can enjoy during their holiday.
The one-, two-, three- bedroom suites come with a balcony with BBQ facilities. Each accommodation is also fitted with a kitchen, a spa bath and private bathroom with free toiletries.
Featuring a huge fireplace, the Clubroom is a great spot to relax. For souvenirs, there’s also an on-site shop that promotes local artists.
The Hotel at Midtown combines the functionality of a state-of-the-art gym and relaxing ambiance of a resort. A haven for fitness enthusiasts, there’s an indoor and outdoor pool, yoga, and sports equipment.
The Penthouse suite features a shower and bathtub for guests to use after an intensive workout.
Babysitting services are also provided so couples can enjoy all the amenities the hotel can offer without having to worry about their kids.
Next on our list of boutique hotels in Chicago is The Majestic Hotel. The vintage vibe and decors make this pet-friendly hotel perfect for an epic weekend getaway. It’s also set near popular attractions and shops.
The leather chairs, wooden fixtures, and decors give off an inviting ambiance. The cozy seating area with fireplace is the perfect spot to bond with family and friends.
All accommodations come with basic amenities such as TV and free toiletries, but certain rooms have a separate seating areas and kitchenette.
Located in the upscale neighborhood of Lincoln Park, this boutique hotel in Chicago features artsy rooms, hallways, lounges, and vibrant fixtures.
The facilities are also accessible for disabled guests. Great dining choices and shops can be found nearby. Fun and hip, the hotel appeals to young couples on a romantic date.
All the rooms are equipped with a coffee machine, TV, and free bath amenities for convenience. Guests are also given free access to the pool at the LA Fitness facility nearby.
Set in Chicago’s Gold Coast region, Viceroy Chicago provides guests with upscale amenities and services that couples on honeymoon will love. It boasts a rooftop bar with a breathtaking view of the surroundings.
Luxurious and relaxing, hues of blue and gold accentuate every corner of the hotel. Some of the rooms, including the Penthouse, offer a view of Lake Michigan, while others have a terrace.
Other facilities that guests can enjoy include the gym, the rooftop pool, and the on-site bar.
Set in the heart of Chicago, this charming boutique hotel features a fitness center and is walking distance from the beach.
Each guest room is fitted with a minibar and floor-to-ceiling windows overlooking a picturesque city view. Experience comfort and an intimate vibe when you visit Chicago to celebrate a special occasion.
Know more about the city’s culture, history and art when you visit one of the points of interest, like the Museum of Contemporary Art.
The Willows is a boutique hotel located near the beach. This hotel is also set on the beautiful Lakeview and Lincoln Park area.
Comfortable and spacious guest rooms with modern room essentials are offered to promote a relaxing ambiance. Couples will surely love their stay in this boutique hotel when they visit Chicago.
For added convenience, the property is also close to public transport and points of interest like Lake Michigan.
Boasting a restaurant, a fitness center, a bar and a shared lounge, this charming hotel is spot worth checking out.
The rooms are spacious and come with essentials like a coffee machine, a minibar, a flat-screen TV and a private bathroom with a shower. These amenities will surely make your stay cozy.
A la carte and American breakfast are also served daily to get you started with your day. Several points of interest are nearby as well.
Here we have another charming hotel set in the heart of Chicago that features nice amenities, like a fitness center.
A flat-screen TV, an iPod dock, a refrigerator, a desk and interesting room decors are standard in each guest room. The rooms are also adorned with wood accents to promote a relaxing and intimate vibe.
Get to learn more about Chicago as you explore the famous Chicago Museum Campus, which is located near the hotel.
The London House located in the heart of Chicago boasts a tri-level rooftop bar and other great facilities.
The guest rooms are fitted with a large workstation, a flat-screen TV along with other room essentials to promote a cozy atmosphere suited for couples celebrating their honeymoon or anniversary.
Modern amenities like a 24-hour fitness center and an on-site restaurant with a terrace overlooking the the river are featured.
If you are looking for a boutique hotel in the center of Chicago check out the Godfrey Hotel.
This boutique hotel features a 24-hour fitness center and spa. Each stylish and spacious room is equipped with a flat-screen TV, a wet bar and a work desk, to give you and your SO a convenient place to stay.
The hotel’s rooftop bar and lounge has a retractable roof and fire pits so you can enjoy your drink in a cozy ambiance.
This boutique hotel in downtown Chicago offers hot tub in select rooms so guests can relax after roaming around the city.
Comfortable spacious rooms, beautiful lounge, and great ambiance, The Allegro Royal Sonesta Hotel is one of the best romantic hotels in Chicago. It’s close to many popular spots and shopping centers in the city.
There’s a happy hour everyday as well as delicious Italian food from the hote’ls on-site restaurants.
A stunning boutique hotel in the center of Chicago that boasts a view of Lake Michigan, on-site restaurants and a rooftop terrace.
Get to spend nights in a spacious luxury room equipped with a flat-screen TV, a work desk, a fully-stocked mini bar and other room essentials that promote a satisfying hotel experience.
Here you will also find a fitness center and restaurant with a casual setting, overlooking a stunning city skyline view.
What is great about boutique hotels is the over all vibe that promotes comfort, satisfaction and intimacy.
Just like the Talbott Hotel in downtown Chicago. This romantic accommodation offers rooms with a flat-screen TV, a climate control system, while select rooms are fitted with a living area and a sofa.
A fitness center and an on-site restaurant are featured, and the property is near several dining options, shopping and entertainment.
Nestled in the heart of Lincoln Park, this classic bed and breakfast is a cozy hotel that will make your vacation more remarkable.
The elegant rooms are fitted with a flat-screen TV, Italian-inspired decors and large windows overlooking a nice neighborhood view. Upscale amenities like a hot tub deck is featured and a Two-Bedroom Suite with Spa Tub.
Popular attractions like the Wrigley Field, Millennium Station and Millennium Park are nearby.
Next on our list of boutique hotels in Chicago is a pet-friendly accommodation that boasts an scenic city view.
Inspired by the Chicago’s World Fair, each guest room also features a flat-screen TV, spacious bathrooms with luxury bathrobes and bath amenities. To top it all, select suites include a sleek spa bath, perfect for couples.
Other modern amenities include a 24-hour fitness center, a pool and free coffee is served every morning at a café next to the hotel.
If you are planning to visit the Windy City, and stay somewhere in River North, check out The Langham Chicago.
Just 20-minutes away from the beach, this hotel offers rooms with the needed room amenities, a deep soaking tub, a rainfall showerhead and luxury bath amenities to promote a relaxing stay.
This hotel also boasts a lake view and 2 restaurants on-site that served American cuisine in an a la carte menu.
The Acme Hotel is an upbeat accommodation with artistic and comfortable rooms, where you can have uninterrupted sleep.
This pet-friendly hotel is set in the heart of Chicago and offers rooms with a smart LED TV, a spacious work desk with a cozy chair and a minibar. Showing its artistic side, the room decors are quite fun and interesting.
A fitness and business center are available on-site and a cocktail lounge that serves crafted cocktails and snacks.
Featuring an impeccable interior design, this hotel gives off a vintage-chic vibe perfect if you’re celebrating a special occasion.
Nestled in the heart of Chicago, this hotel offers rooms with a seating area, a desk and a flat-screen TV to promote a feel at home and cozy vibe. Different room types are also offered to suit your preference.
This accommodation has a fitness center, a bar and a restaurant. The Magnificent Mile is also just a 10-minute walk from the property.
Classic and scenic describe this next hotel. It has spacious units and is set in the heart of the city.
The rooms feature a view and other room facilities like a TV with cable channels, soundproof walls, a desk and a seating area to name a few. It’s a nice hotel for travelers who are looking for any form of inspiration.
A fitness center is available on-site and points of interest like the Oak Street Beach is only a 10 minute walk from the hotel.
The Harvey House is an intimate bed and breakfast that features a warm and cozy space, great relaxation.
Each guest room is fitted with a flat-screen TV, a DVD player, and a refrigerator. A number of rooms are also offered, including a Queen Room and a King Suite with a Spa Bath to soothe you after a long and fun day.
Hot breakfast is served every day, with an array of choices from oven pancakes, French toast to local organic food.
Related: Prestige hotels in Chicago.
Nestled in the heart of Chicago, this elegant hotel boast beautiful city views as well as contemporary and spacious rooms.
All rooms have modern designs and are provided with a flat-screen TV, a microwave, and a refrigerator. Select rooms also feature a balcony or a sofa bed, and a sleek deep soaking tub.
Upscale amenities like a swimming pool, a spa and wellness center, and a bar are featured at this pet-friendly hotel.
Here’s another boutique hotel set in the heart of Chicago that features an urban-chic and inspiring vibe.
This beautiful and timeless hotel features rooms with coffee-making facilities, a minibar, a seating area and a work desk. A marble deep soaking tub is also featured in select rooms, and a stunning view of the city.
There is also a fitness center on-site and the property is close to Willis Tower and high-end shopping options.
If you want to find more romantic hotels in Chicago, IL, click on one of our lists for your next getaway or vacation. And if you want to check out more boutique hotels in the USA, see the boutique homepage.
For more romantic options, check out the menu.
Featuring artsy hallways, vibrant yet comfortable rooms, and great dining options nearby, Hotel Versey Days Inn by Wyndham Chicago is the best hotel for young couples. It's conveniently located close to many shops, bars, and restaurants.
The Hotel at Midtown. Not only is the neighborhood safe, but the hotel itself offers babysitting services for an additional charge.
The Guesthouse Hotel is another great choice for families. There's a barbecue facility that families can use after a day of traveling around the city.
Great for anniversaries and weekend romantic dates, the Hampton Inn & Suites Chicago North Shore features a Spa Bath that couples can enjoy. Delicious hearty breakfast is also served at the Inn everyday.
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