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Bed and breakfast vacation rentals in North Side

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Top-rated bed and breakfasts in North 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

4.82 out of 5 average rating, 429 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

5.0 out of 5 average rating, 105 reviews
Top 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).

4.95 out of 5 average rating, 309 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.

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

4.96 out of 5 average rating, 312 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.

5.0 out of 5 average rating, 171 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

4.83 out of 5 average rating, 431 reviews
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 Lake View

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."

4.91 out of 5 average rating, 391 reviewsA 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.

4.81 out of 5 average rating, 180 reviewsA 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.

4.84 out of 5 average rating, 32 reviewsA 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.

4.76 out of 5 average rating, 360 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.

4.92 out of 5 average rating, 83 reviews

Popular amenities for North Side bed and breakfasts

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly bed and breakfasts

Top guest favourite
A fire pit placed on grass is surrounded by two chairs, creating a cozy gathering space. Flames dance brightly against the night backdrop, and a wooden fence provides privacy. The area is softly illuminated, inviting relaxation in the outdoor setting.
Guest suite in Lake Zurich

Private Guest Suite • Sleeps 4 • Separate Entrance

4.93 out of 5 average rating, 68 reviewsA spacious bedroom features a patterned blue accent wall and a wooden artwork above the bed. A comfortable bed is dressed in neutral linens, flanked by two bedside tables with reading lamps. A ceiling fan and natural light from a window enhance the inviting ambiance.
Private room in Bronzeville

Dubois Guest House Room 102

4.73 out of 5 average rating, 55 reviews
Private room in Edgewater

House 5863 Bed and Breakfast Room 2

4.71 out of 5 average rating, 28 reviewsA bright bedroom is featured, showcasing a large bed with neutral bedding accented by a textured throw. A red shelf adds a modern touch to the wall, while floral wallpaper enhances the space. Natural light is invited through a window, framed by white curtains.
Private room in Bronzeville

Villa Dubois Guest House Room 3

4.63 out of 5 average rating, 8 reviews
Private room in Edgewater

House 5863 Bed and Breakfast Room 5

5.0 out of 5 average rating, 18 reviewsA spacious room features a bed with a gray coverlet, accentuated by a wall with subtle patterned wallpaper. A wooden nightstand is present next to the bed, while a stylish chair and area rug add warmth. Curtains frame a window, allowing diffused light into the space.
Private room in Bronzeville

Dubois Guest House Room 101

4.49 out of 5 average rating, 39 reviews

Bed and breakfast rentals with breakfast

Superhost
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.
Private room in Lake View

Large private room w/ shared bathroom in Boystown!

4.83 out of 5 average rating, 407 reviews
Top guest favourite
A bright bedroom is shown with a spacious bed adorned with blue and orange accents. Natural light filters through white-framed windows, highlighting the warm wooden floors and soft textures. A dresser and seating area are present, contributing to a functional and inviting layout.
Private room in Hyde Park

Lovely UofC Prof mansion great on campus location

4.99 out of 5 average rating, 122 reviews
Superhost
The room features a spacious bed dressed in a dark patterned blanket. A pair of bedside lamps illuminate the area, providing soft light. A framed black-and-white photograph adorns the wall above the bed, and yellow curtains add a touch of color to the room.
Private room in Lake View

Queen Bed with Private Bath in Boystown

4.75 out of 5 average rating, 356 reviews
Superhost
A cozy sleeping area is presented with a round bed adorned in dark blue bedding featuring intricate patterns. The wall is decorated with two framed circular artworks, and natural light enters through a window dressed with patterned curtains.
Private room in Lake View

Cute room in downtown Boystown

4.77 out of 5 average rating, 391 reviews
Superhost
A compact room features a full-sized bed, a digital television mounted on the wall, and a decorative mirror. A small folding chair is positioned near an elegant side table. Light-coloured wall tiles and soft drapes add a touch of sophistication to the intimate space.
Private room in Lake View

Cozy Garden Room in the middle of Boystown!

4.76 out of 5 average rating, 372 reviews
Superhost
A cozy bedroom features rich, burgundy walls and patterned bedding. The space is defined by soft, flowing curtains that separate the area. Framed artwork is displayed on the walls, and a mirror reflects light, adding depth to the intimate ambiance.
Private room in Lake View

British Themed Room in the Middle of Boystown

4.79 out of 5 average rating, 374 reviews
Superhost
A compact bedroom is accessed through a wooden door. The walls are painted a warm red hue, complemented by rich brown curtains. A dark wood headboard supports a neatly made bed with black bedding and decorative pillows. A bedside lamp casts a gentle glow.
Private room in Lake View

Private room with private entrance in Boystown

4.85 out of 5 average rating, 341 reviews
Top guest favourite
The warm room features a spacious bed with a colorful throw, complemented by two large windows adorned with potted plants. A comfortable work desk and chair are positioned nearby, while a small bench and decorative baskets provide additional storage.
Private room in Hyde Park

Top location, sunny UofC Prof on campus home

4.95 out of 5 average rating, 143 reviews

Other bed and breakfast vacation rentals

Private room in South Side

Historic home close to Obama Center, by Metra

4.74 out of 5 average rating, 34 reviews
Superhost
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.
Private room in Lake View

Blue Room in Dorothy's BNB

4.67 out of 5 average rating, 18 reviews
Superhost
A cozy sleeping area is highlighted by soft grey walls and adorned with framed artwork of floral arrangements. A dark quilt covers the spacious bed, accentuated by a textured throw and decorative pillows. A wall sconce provides warm lighting, enhancing the inviting atmosphere.
Private room in Lake View

Private ensuite bedroom and bathroom

4.92 out of 5 average rating, 13 reviews
Top guest favourite
The elegant living area features a crystal chandelier overhead, with a mixture of white and dark wood furniture. Colorful cushions are placed on the sofas, and a glass coffee table showcases decorative items. A large mirror reflects the inviting atmosphere, with glimpses of the kitchen area visible in the background.
Private room in Hyde Park

Historic campus house owned by U of C Prof

4.94 out of 5 average rating, 70 reviews
Superhost
A modern guest room corner features a spacious bed with crisp white linens and a purple upholstered headboard. A sleek bedside table holds two glass water bottles and a small plant. A decorative wall with floral and butterfly patterns adds a touch of color.
Hotel room in Wicker Park

Spacious King Room in Boutique Wicker Park B&B

5.0 out of 5 average rating, 5 reviews
Superhost
A cozy bed with crisp white linens is set against a floral accent wall featuring vibrant pink and yellow blooms. A decorative headboard adds elegance, while a small potted plant sits on a marble side table, complementing the room's modern design.
Hotel room in Wicker Park

Luxurious King Room in Boutique Wicker Park B&B

4.75 out of 5 average rating, 4 reviews
Guest favourite
A modern guest room features a king-size bed with an upholstered headboard against an exposed brick wall. A wallpapered wall adds a subtle design element. Soft light pours in from a skylight, while gold sconces illuminate the space. A sleek bedside table complements the decor.
Hotel room in Wicker Park

Gorgeous King Room in Boutique Wicker Park B&B

4.96 out of 5 average rating, 28 reviews
Superhost
A modern guest room features a king-size bed with crisp white linens, complemented by a decorative gray blanket. An exposed brick wall and floral accent wall create a stylish backdrop. A wall-mounted TV and a small desk area are visible, along with a decorative fireplace.
Hotel room in Wicker Park

Romantic King Room in Boutique Wicker Park B&B

4.82 out of 5 average rating, 28 reviews

Destinations to explore