Bed and breakfast holiday rentals in Chicago

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.

4.99 out of 5 average rating, 122 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

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Private room in South Side

4.76 out of 5 average rating, 37 reviews

Historic home close to Obama Center, by Metra

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: • Proximity to Obama Presidential Center • Close to Lake Shore Drive, Hyde Park • Border w/Jackson Park Highlands & Golf Course • 21-min drive downtown • Short Metra ride to UChicago, Museum of Science & Industry, McCormick Place, Grant Park, Millennium Park & Loop • Steps to Starbucks, markets, laundromat & fast food • Street parking

ValueLocationHospitality

4.95 out of 5 average rating, 312 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).

ValueFamilyWalkability

Hotel room in Lincoln Park

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.

4.96 out of 5 average rating, 23 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.

LocationBathroomAccuracy

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, 316 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

ValueFamilyTV

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, 172 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.

ValueFamilyGrill

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.

4.78 out of 5 average rating, 375 reviews

British Themed Room in the Middle of 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

LocationValueAmenities

Private room in East Rogers Park

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.

4.83 out of 5 average rating, 435 reviews

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

ValueLocationAccess

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

4.81 out of 5 average rating, 180 reviews

#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.

LocationFamilyComfort

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

4.76 out of 5 average rating, 361 reviews

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.

LocationValueLaundry

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.

4.92 out of 5 average rating, 83 reviews

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.

LocationValueAccuracy

A cozy bedroom is characterized by a full-sized bed dressed in a textured blue cover, complemented by yellow decorative pillows. The wall features three framed black-and-white photographs, while a brick wall adds a rustic touch. A ceiling fan is present above.

4.89 out of 5 average rating, 19 reviews

Private bedroom with shared bath

Located in the heart of Boystown, this private room has a full sized bed, shares two bathrooms with three other rooms, shared kitchen, shared living room and dining room. Wifi throughout the property. Main thing to be aware of, is due to its centrality, it can be loud, especially at night on weekends. Weekly cleaning of all shared spaces included.

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Popular amenities for bed & breakfast rentals in Chicago

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly bed & breakfast rentals

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.

4.94 out of 5 average rating, 70 reviews

Historic campus house owned by U of C Prof

LocationValueHospitality

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, 20 reviews

Blue Room in Dorothy's BNB

ValueLocationWalkability

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.

4.9 out of 5 average rating, 10 reviews

Four bedroom apartment

LocationCheck-inHospitality

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.

4.92 out of 5 average rating, 13 reviews

Private ensuite bedroom and bathroom

ValueLocationHospitality

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.

5.0 out of 5 average rating, 5 reviews

Spacious King Room in Boutique Wicker Park B&B

LocationComfortDecor

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.

4.75 out of 5 average rating, 4 reviews

Luxurious King Room in Boutique Wicker Park B&B

LocationCheckoutHospitality

A guest room features a queen-size bed with crisp white linens and a decorative headboard. A vibrant floral accent wall adds color, while a dark armchair sits beside a small round table with a gold vase. A wall-mounted lamp provides soft lighting.

5.0 out of 5 average rating, 6 reviews

Romantic Queen Room in Boutique Wicker Park B&B

LocationBreakfastHospitality

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.

4.96 out of 5 average rating, 28 reviews

Gorgeous King Room in Boutique Wicker Park B&B

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Bed and breakfast rentals with breakfast

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, 106 reviews

Historic campus U of C Prof. mansion, top location

FamilyValueAmenities

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, 410 reviews

Large private room w/ shared bathroom in Boystown!

FamilyValueHospitality

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, 431 reviews

Bright Room with a Garden View

LocationValueCheckout

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.

4.77 out of 5 average rating, 391 reviews

Cute room in downtown Boystown

ValueLocationOutdoor spaces

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.

4.95 out of 5 average rating, 143 reviews

Top location, sunny UofC Prof on campus home

LocationValueGetting around

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.

4.75 out of 5 average rating, 359 reviews

Queen Bed with Private Bath in Boystown

FamilyLocationPets

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.

4.76 out of 5 average rating, 373 reviews

Cozy Garden Room in the middle of Boystown!

ValueLocationLong stay

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.