Bed and breakfast holiday rentals in West Side

Find and book unique bed and breakfasts on Airbnb

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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Superhost

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.

Private room in Lake View

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

LocationFamilyGetting around

4.82 out of 5 average rating, 431 reviews

Top Guest favourite

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.

Private room in Hyde Park

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

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 106 reviews

Private room in South Side

Historic Coliving by Metra, close to Obama Center

Stay in our historic 1900s brick home in the South Side, or Chicago’s iconic Black district. Imagine living like locals in this up-and-coming neighborhood. Enjoy: • 21-min drive downtown • Short drive to Obama Presidential Center • Close to Hyde Park, Lake Shore Drive • Border w/Jackson Park Highlands & Golf Course • Quick Metra ride to UChicago, Museum of Science & Industry, McCormick Place, Grant Park, Millennium Park, Loop • Steps to Starbucks, markets, laundromat, fast food • Street parking

ValueLocationSleep quality

4.76 out of 5 average rating, 37 reviews

Guest favourite

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).

LocationFamilyBreakfast

4.95 out of 5 average rating, 315 reviews

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

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.

LocationCheck-inHospitality

4.96 out of 5 average rating, 23 reviews

Top Guest favourite

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.

Private room in Edgewater

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

ValueFamilyView

4.96 out of 5 average rating, 316 reviews

Top Guest favourite

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.

Private room in South Loop

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.

ValueLocationCheck-in

5.0 out of 5 average rating, 173 reviews

Guest favourite

A city skyline is illuminated at dusk, showcasing tall buildings and a prominent river on the left side. The streets are lined with light, creating a vibrant atmosphere as the city transitions into night.

Private room in East Rogers Park

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

ValueLocationIndoor spaces

4.83 out of 5 average rating, 435 reviews

A spacious living area is observed with a comfortable blue sofa adorned with patterned cushions. A green armchair is positioned nearby. A decorative coffee table with a tray sits on a patterned rug. Light streams in from windows, and the blue wall adds a calming backdrop.

Private room in East Rogers Park

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)

The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan - perfect for gatherings of any kind. We're in the heart of the Rogers Park, walking distance from many restaurants & shops, one block from Loyola Beach Park, and 5-15 mins walk to 2 different train / metro lines. The home is run by friendly local folks who are happy to help during your stay.

LocationValueLaundry

4.81 out of 5 average rating, 180 reviews

A spacious bedroom features a large upholstered bed covered with a blue blanket. Highlighted by natural light from tall windows, a mix of blue and beige walls harmonizes with decorative wall art. A small plant adds a touch of greenery to the inviting space.

Private room in Bronzeville

Villa Dubois Guest House Room 1

Villa Dubois Guest House is 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 McCormick Convention Center. Room 1 is a private room with shared bathroom for up to 2 guests. It is one of our largest and brightest room.

LocationFamilyNearby

4.84 out of 5 average rating, 32 reviews

A two-story brick house is showcased, featuring a welcoming front staircase. Large windows are framed with neatly arranged flower pots, and a manicured hedge borders the lawn. The surrounding area consists of well-maintained sidewalks and neighboring homes, contributing to a quiet suburban feel.

Private room in Norwood Park

Chicago River Room, near Med Ctr

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

LocationValueCheckout

4.76 out of 5 average rating, 363 reviews

Guest favourite

A modern guest room features a colorful floral accent wall behind a plush blue headboard. A silver nightstand complements the design, topped with a decorative vase. Soft white bedding and a neutral quilt create a cozy sleeping area that invites relaxation.

Hotel room in Wicker Park

King Room in Boutique Wicker Park B&B

Modern guest room located on the main floor just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Ellen 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.

LocationValueHospitality

4.92 out of 5 average rating, 83 reviews