Boutique hotel vacation rentals in Chicago

Find and book unique boutique hotels on Airbnb

Top-rated boutique hotels in Chicago

Guests agree: these boutique hotel rentals are highly rated for location, cleanliness, and more.

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Superhost
A spacious bed is positioned against a map-themed accent wall, featuring the word 'hello' on the decorative pillow. Nightstands with lamps are placed on either side, providing functionality and style. The room is well-lit with natural tones enhancing the relaxed ambiance.
Hotel room in Chicago Loop
4.83 out of 5 average rating, 36 reviews

King Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Superhost
A modern guest room showcases a large bed with a decorative pillow against a graphic wall map of the city. A comfortable gray sofa sits across from it, accompanied by a table featuring a lamp. Natural light enters through a large window.
Hotel room in Chicago Loop
4.8 out of 5 average rating, 207 reviews

Spacious Hotel Room in The Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

Superhost
A spacious bed is centered against a wall featuring a vintage map design of Lake Michigan. Nightstands on either side are equipped with modern lamps, and a decorative pillow with the word 'hello' rests on the bed, enhancing the inviting atmosphere.
Hotel room in Chicago Loop
4.76 out of 5 average rating, 66 reviews

Charming King Bedroom in Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

A spacious bedroom is highlighted by a large bed with crisp white linens. Flanking the bed are two wooden nightstands, each topped with unique lamps. A cozy bench is positioned at the foot of the bed, and large windows provide natural light.
Hotel room in Streeterville
4.69 out of 5 average rating, 432 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Hotel room in South Loop
4.2 out of 5 average rating, 15 reviews

Budget-Friendly Room| Free Coffee | Downtown

Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and walking distance to some of the city’s top attractions, this space is ideal for solo travelers looking to explore, work, or simply unwind in comfort. Whether you're in town for business, a quick getaway, or solo sightseeing, this room offers everything you need in a location that puts Chicago at your fingertips.

A well-appointed sleeping area features a spacious bed with a minimalist headboard. Soft pillows in various hues are arranged at the head of the bed. A bedside lamp provides warm illumination, and a small table holds amenities.
Hotel room in Grant Park
4.44 out of 5 average rating, 529 reviews

Standard King Room

The Standard King Rooms feature one King bed as well as a decorative round table and two chairs. Amenities include: Complimentary wireless Internet, Coffeemaker and coffee, Iron/ironing board, Mini refrigerator, Pillowtop beds , Hairdryer, Room service, Flat-screen TV with cable and satellite channels and a Safe deposit box. Heating and Air condition based on temperature out side

Superhost
A guest room features a spacious bed with a soft blanket, complemented by a stylish headboard. A desk and lamp are visible beside the bed, while soft natural light filters through the window. The room's decor incorporates subtle blue tones inspired by Chicago.
Hotel room in Chicago Loop
4.67 out of 5 average rating, 9 reviews

Charming Private Room in Downtown

Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Unwind and relax in our comfortable guest rooms with Chicago-inspired décor. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

An elegant lobby is highlighted by polished marble flooring and intricate light fixtures. Gold-accented foliage decorates the space, complementing a minimalist reception area with a sleek counter. Dark walls adorned with bookshelves create a sophisticated backdrop.
Hotel room in Arlington Heights
4.72 out of 5 average rating, 167 reviews

Chez Hotel King Room

Experience luxury at Chez Hotel, a chic boutique escape in Arlington Heights, IL. Enjoy elegant rooms, modern amenities, fine dining, and a stunning rooftop with panoramic views. Perfect for business or leisure stays, just minutes from shopping, entertainment, and O’Hare Airport.

Guest favourite
A comfortable sleeping area is highlighted by a spacious bed with a gray and white striped blanket. A television is mounted on the wall, while a coffee maker and wastebasket are positioned nearby. Natural light filters through the window, adorned with black blinds. A robe is hanging on a wall rack.
Hotel room in Plainfield
4.98 out of 5 average rating, 57 reviews

Herrington Suite - The Plainfield Inn

APPROX. 11 X 11 · PRIVATE BATH · NORTHERN EXPOSURE This is the last room in the original house with northern exposure. It is named for the Goodson's daughter who married Robert Herrington. She moved back into the home in 1908 when they inherited the property.

Superhost
A modern guest room featuring a spacious bed with soft linens, complemented by a decorative accent wall. Natural light filters through a window, illuminating the warm wood flooring. A small workspace with a desk and lamp is positioned nearby, enhancing the room's functional design.
Hotel room in Chicago Loop
4.52 out of 5 average rating, 25 reviews

King Bedroom in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations.

Superhost
A spacious bed is positioned against a creatively designed wall featuring a map graphic in soft hues. Flanking the bed are matching bedside lamps that provide warm lighting. A neutral-textured throw blanket lies atop the bed, adding an element of comfort.
Hotel room in Chicago Loop
4.8 out of 5 average rating, 15 reviews

Private King Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations.

Superhost
A spacious bed is centered in the room, complemented by two nightstands with lamps on each side. A muted map design in the background features local landmarks. A decorative pillow with the word 'hello' adds a welcoming touch.
Hotel room in Chicago Loop
4.67 out of 5 average rating, 48 reviews

Private King Bedroom in Heart of Downtown Chicago

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations.

Popular amenities for Chicago boutique hotels

Quick stats about boutique hotel rentals in Chicago

  • Total vacation rentals

    Explore 30 vacation rentals in Chicago

  • Nightly prices starting at

    Chicago vacation rentals start at $98 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,200 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Chicago vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chicago rentals

  • 4.7 Average rating

    Chicago stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Chicago’s top spots, include Millennium Park, Wrigley Field, and Lincoln Park

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Boutique hotel rentals