Bed and breakfast holiday rentals in West Side

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Top-rated bed and breakfasts in West Side

Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.

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A spacious room features a king bed adorned with a decorative duvet and colorful accent pillows. Natural light enters through a window, illuminating the wood floors. A ceiling fan is installed, and a small rug is placed at the foot of the bed, contributing to the room's comfort.
Private room in Chicago
5 out of 5 average rating, 8 reviews

House 5863 Bed and Breakfast Room 4

Room 4 Features: King bed In-suite bath Flat-screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bathrobes All Rooms include Central Heat/ Air Conditioning Room 4 is our brightest room and has the added benefit of having direct access to our common deck area. The room also features a pull-out sofa and can accommodate an additional guest (Subject to additional charge). * All guests must be fully vaccinated for Covid-19 and at least 2 weeks after 2nd shot. * City of Chicago Bed and Breakfast License Number #2207267

Top Guest favourite
Private room in Chicago
4.99 out of 5 average rating, 121 reviews

Lovely UofC Prof mansion great on campus location

No closer accommodation to U of C anywhere. Large light filled bedrooms, private bathrooms, huge balcony in 4 story light filled home on sought after University of Chicago campus. Two blocks from the University, four blocks from Lab school. Short walk to train to downtown, beach, bike path, Science and Industry Museum and lakefront. A rare, privately owned home in the heart of campus. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Top Guest favourite
A spacious master bedroom with light yellow walls features a California King bed adorned with decorative pillows. A wooden nightstand with a lamp is positioned on either side of the bed. A vintage dressing table, bookshelves, and floral arrangements enhance the inviting atmosphere.
Private room in Chicago
5 out of 5 average rating, 98 reviews

Historic campus U of C Prof. mansion, top location

NO closer location to the Univ. of Chicago. This large on-campus master suite features beautiful hardwood oak floors, big windows overlooking the front of the house, luxurious sauna bath, glass enclosed shower, heated bathroom floors, dressing area, vintage ladies dressing table and cheval mirror, work desk, and Cal King bed. Minutes from dorms and main campus. Large shared kitchen and deck. See all 5 rooms avail. in our bed and breakfast: here:https://airbnb.com/users/143937691/listings

Top Guest favourite
Private room in Chicago
4.95 out of 5 average rating, 136 reviews

Top location, sunny UofC Prof on campus home

NO closer accommodation to the U of c campus, large wrap around deck with garden and small semi private deck. convenient access to lakefront, Obama house, Science and Industry museum, public transport. Excellent do it yourself morning breakfast in large kitchen, sparkling clean home. Newly renovated room, marble bathroom floors. More like a traditional bed and breakfast than airbnb. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Guest favourite
Private room in Wilmette
4.95 out of 5 average rating, 281 reviews

(BR#1) Welcoming, warm & comfortable, 3 guests

Welcoming, warm & comfortable home, BR#1 for up to 3 guests. (LISTING #1 OF 3; see other listings for additional space.) A lovely and spacious bedroom in our home. Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Meaningful conversation (if you want it).

Top Guest favourite
Private room in Chicago
4.95 out of 5 average rating, 288 reviews

Great Edgewater/Andersonville private suite

1904 Greystone 2-Flat gut rehabbed into Single Family Home: Loft style w/ exposed brick & duct work. Private guest suite (w/ separate entrance) that sleeps 2-4 persons, There is a King bed in the private bedroom & queen tempurpedic topped sofa sleeper in the private living area, wet bar w/ mini fridge, Keurig coffee maker, sink and microwave, 2 flat screens TVs, private bath, piano, and use of the backyard garden. Also, the main house Kitchen/Living Rm are available to use upon request

Top Guest favourite
Private room in Chicago
5 out of 5 average rating, 149 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, and balcony.

Superhost
A cozy sleeping area features a spacious bed covered with a textured blue blanket, accompanied by vibrant yellow pillows. The wall is painted in a deep blue shade, while exposed brick adds a rustic touch. Three framed black-and-white artworks hang above the bed.
Private room in Chicago
4.9 out of 5 average rating, 10 reviews

Four bedroom apartment

Located in the middle of Chicago's Iconic Boystown in the Lakeview neighborhood, this four bedroom (2 queen beds, 2 full) two bathroom can sleep eight people in the four rooms and two people on a pull out sofa. There is a full kitchen, small washer and dryer, wifi, and a couple of small eating areas. This room is on the third floor and does not have an elevator. Continental breakfast is included at the neighboring property. Please note some rooms can be loud due to street noise.

Superhost
Private room in Chicago
4.55 out of 5 average rating, 11 reviews

Blue Room in Dorothy's BNB

Located right in the middle of Boystown in the Lakeview this room has a queen bed with two shared bathrooms. Central ac and heat. Wifi, continental breakfast, included. The space has a shared kitchen, washer and dryer, living room, dining area. This space is shared with three other bedrooms and is located right off Halsted street, so if you are sensitive to noise, this may not be the right room for you. There is no parking on site, street parking only, permits available.

Private room in Chicago
4.84 out of 5 average rating, 386 reviews

Large private room w/ shared bathroom in Boystown!

Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Top Guest favourite
A bright family room features large windows allowing natural light to filter in. Two armchairs are positioned near a coffee table stacked with books. An exercise bike is against a wall, and a television is mounted above a fireplace, enhancing the room's functionality.
Private room in Chicago
4.91 out of 5 average rating, 378 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access to a one bed/bath with additional access to the bright spacious family room. Located minutes from bus, DIVVY bikes, and "el" (2 blocks), Wrigley Field (6 blocks) and 1.5 miles to Lake Michigan. Walk Approximately 20 minutes by train to the downtown area or central city "Loop."

A spacious bedroom features a queen bed with a dark quilt and two decorative pillows. Natural light streams in through two windows, revealing a neutral color palette and patterned wallpaper. A minimalist shelf and a wooden chair complete the room's inviting design.
Private room in Chicago
4.68 out of 5 average rating, 37 reviews

Wrigleyville Suites Room 1

Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe, just minutes away from local restaurants, downtown, public transit (both bus and train), Divvy Bike Stations, and Cubs Stadium. Room 1 is a private room with a queen bed and shared bathroom for up to 2 guests. It is one of our largest and brightest room.

Popular amenities for West Side bed and breakfasts

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