Bed and breakfast holiday rentals in West Side

An inviting bedroom features a spacious bed adorned with crisp white linens and a decorative black pillow. Metallic bedside tables are positioned on either side, and a stylish bench sits at the foot of the bed. Natural light is filtered through elegant curtains.

4.82 out of 5 average rating, 427 reviews

Bright Room with a Garden View

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. Shares bathroom with 2 rooms Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

FamilyLocationAir conditioning

Private room in Hyde Park

A bright bedroom is highlighted with soft yellow walls and hardwood floors. A California King bed is dressed in a yellow coverlet, flanked by decorative pillows. Natural light filters through multiple windows, while a TV and workspace are visible across the room. A potted plant adds a touch of greenery.

5.0 out of 5 average rating, 102 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

LocationFamilySolo travel

4.95 out of 5 average rating, 306 reviews

The bedroom features two beds, one with a pastel blue coverlet and decorative pillows in shades of coral and teal. A large mirror leans against the wall beside a white dresser. Natural light filters through sheer curtains across two windows.

Private room in Wilmette

(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).

LocationFamilyQuiet

Guest favourite

A cozy bedroom features a king bed with white linens and decorative pillows. A dark wood nightstand and lamp are positioned beside the bed. Rich curtains frame a window, while an upholstered armchair adds a pop of color, enhancing the room's inviting atmosphere.

Hotel room in Lincoln Park

4.95 out of 5 average rating, 22 reviews

Lincoln Park Guest House

Bed and Breakfast license issued by the City of Chicago # 2398451. Hosts live onsite. The private guest suite features a two-story cathedral ceiling with skylights, king bed is upholstered in leather with a memory foam mattress and premium Vera Wang linens. Private bath with personal amenities. mini-refrigerator stocked with bottled water and and a Keurig machine with coffee. Daily housekeeping provided. Property not ADA accessible. Thirteen steps lead from street level to front door.

LocationHospitalityGetting around

Private room in Edgewater

A spacious living area features a comfortable sofa and a wooden coffee table, complemented by a variety of artwork on the walls. A dining table with dark chairs is present, along with a kitchenette area containing a refrigerator and cabinets.

4.96 out of 5 average rating, 308 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

LocationFamilyBeach

Private room in South Loop

The private bedroom features a plush bed with a vibrant red coverlet and decorative pillows. Framed art pieces adorn the wall above the bed, while a cozy stuffed toy adds a touch of warmth. A small bedside table and a door to the en-suite bathroom are visible.

5.0 out of 5 average rating, 167 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.

LocationFamilyQuiet

The kitchen features dark wooden cabinets and a black countertop. A stainless steel dishwasher and oven are visible, alongside a coffee maker and other appliances. A glass-top dining table with four black chairs occupies part of the space, creating an inviting area for meals.

4.65 out of 5 average rating, 17 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.

ValueLocationCleanliness

A cozy bedroom showcases a curved wooden bed with a coral-colored comforter and decorative pillows. Flanking the bed are two wall sconces providing soft lighting. A skylight allows natural light to brighten the room, while a vintage-style mirror hangs above the bed. A small stacked storage unit sits nearby.

4.83 out of 5 average rating, 405 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

ValueLocationWalkability

Hotel room in Wicker Park

A modern guest room is presented with a king-size bed dressed in crisp white linens. Unique wall art features a bird motif, complemented by stylish brass sconces. A geometric pendant light hangs above, enhancing the room's contemporary appeal. Framed photos add a personal touch.

5.0 out of 5 average rating, 6 reviews

Sun-Filled King Room in Boutique Wicker Park B&B

Bright and modern guest room located on the second floor with a lovely view of our quiet, tree-lined street. Just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Concord King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood.

LocationAir conditioningView

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.