Bed and breakfast vacation rentals in Chicago

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Popular amenities for Chicago bed and breakfast rentals

Family-friendly bed and breakfast rentals

Top guest favorite
Private room in Andersonville
4.95 out of 5 average rating, 257 reviews

Great Edgewater/Andersonville private suite

ThomasRating, 5 stars1 week ago
Tripp and Todd's home is gorgeous, and they are both so friendly and accommodating it feels like coming home. The unit has a private entrance if you want to utilize it though I more often came through the front door instead just to chat with them. They're both very knowledgeable about the area and made great recommendations, suggesting some food options that were new to me even though I am regularly in the are. The bed was very comfortable and the downstairs suite is very well set up for a stay. I highly recommend their place!
Top guest favorite
A spacious living area is highlighted by large windows that invite natural light, revealing a chandelier above and a decorative mirror on the wall. Comfortable seating arrangements include white sofas and a glass coffee table. A bouquet of flowers adds a touch of elegance to the room.
Private room in Hyde Park
4.99 out of 5 average rating, 109 reviews

Lovely UofC Prof mansion great on campus location

KalynRating, 5 stars1 month ago
The hosts were great, and the property is beautiful! Our room was very clean and felt very private.
Top guest favorite
Private room in Evanston
4.97 out of 5 average rating, 571 reviews

Classy and Cozy home in Evanston

SarahRating, 5 stars1 month ago
Patricia’s place was perfect and it was so welcoming and comfortable. The conversation and home cooked breakfast was lovely. We would recommend this place to anyone in the area. What a gem!
Top guest favorite
Private room in Evanston
4.95 out of 5 average rating, 486 reviews

Classy and Cozy 2nd. Room

ReneeRating, 5 stars4 weeks ago
The hosts are fascinating, lovely people who boosted our spirits during a stressful search for a house in the Chicago area. They serve a delicious breakfast, and even brought me a special treat with a candle when I said it was my birthday! The neighborhood is peaceful and the house is very comfortable. We didn’t find a house to buy, but we feel we found friends.

Bed and breakfast rentals with breakfast

Superhost
A modern kitchen features a large island with a patterned backsplash and four orange stools. Light blue cabinetry contrasts with stainless steel appliances, including a refrigerator and an oven. A sleek range hood is suspended above the cooktop, complementing the bright and airy space.
Hotel room in Wicker Park
5 out of 5 average rating, 6 reviews

Romantic Queen Room in Boutique Wicker Park B&B

ElizabethRating, 5 stars26 months ago
Everything was perfect! Enjoyed the room and breakfast. Staff was very friendly and helpful.
Top guest favorite
Private room in Hyde Park
5 out of 5 average rating, 84 reviews

Historic campus U of C Prof. mansion, top location

AmyRating, 5 stars1 week ago
Our stay was absolutely lovely. Caryl was extremely communicative, welcoming, and makes a fantastic breakfast. The home and our room were beautiful and perfectly located for anyone visiting U Chicago. The interactions with the other guests and host at breakfast were a special treat.
Top guest favorite
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
4.93 out of 5 average rating, 61 reviews

Historic campus house owned by U of C Prof

CaseyRating, 5 stars6 months ago
Caryl was a wonderful host who went above and beyond to make sure I was comfortable. My room had everything I needed, and the house is a convenient walk to UChicago. I will definitely be staying here again on future visits!
Superhost
A modern kitchen is designed with mint-green cabinetry and a patterned backsplash. A central island features a white countertop with four orange stools arranged neatly. Stainless steel appliances, including a refrigerator and oven, enhance the sleek aesthetic of the space.
Hotel room in Wicker Park
5 out of 5 average rating, 5 reviews

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

AnnieRating, 5 stars26 months ago
A lovely room, clean and cozy, in a great location. Very walkable! My room was first floor street-facing and I didn’t notice any outdoor noise (expect a little rumble from the train). Laura was incredibly responsive and helpful. I’d stay here again. I didn’t want to pay for parking, and I’m familiar with the neighborhood, so I chose to park several blocks away.
Superhost
A cozy guest room is highlighted by a vibrant floral accent wall in teal and purple. A plush headboard and white bedding are paired with a small side table, while a mirror reflects a modern aesthetic. Natural light enhances the inviting atmosphere.
Hotel room in Wicker Park
4.85 out of 5 average rating, 48 reviews

Queen Room w/ Balcony in Boutique Wicker Park B&B

JeanRating, 5 stars5 months ago
It was a wonderful stay with a very hospitable host. We loved the access to the beautiful kitchen with instant hot water for tea. The homemade baked goods were a delicious treat in the morning. The room was immaculate. The back rooms face the tracks for the busy Chicago Transit Blue Line, so if noise bothers you, ask for a room facing the street.
Superhost
Private room in Norwood Park
4.78 out of 5 average rating, 266 reviews

Cloudgate Room, minutes to O'Hare in Safest Area

Vinod KumarRating, 5 stars6 months ago
Fair value for the stay
Superhost
A guest room features a king-size bed dressed in white linens, complemented by a textured gray blanket. Dark curtains frame two windows, allowing natural light. A decorative fireplace is positioned against a wall adorned with floral wallpaper, adding a touch of elegance. A circular mirror hangs above the bed.
Hotel room in Wicker Park
4.75 out of 5 average rating, 4 reviews

Luxurious King Room in Boutique Wicker Park B&B

AmandaRating, 5 stars26 months ago
This place is the perfect spot. Nice and clean and the building admin that check you in are wonderful. Totally would come back again.
The room features a spacious king bed with a dark headboard and white linens. A private in-room jacuzzi tub is positioned near a wall-mounted TV. A set of floor-to-ceiling curtains allows natural light to enter, creating a comfortable ambiance.
Private room in Westmont
3.33 out of 5 average rating, 3 reviews

King Bed with Jet Tub

LartezRating, 5 stars1 month ago
Nice chill spot

Quick stats about bed and breakfast rentals in Chicago

  • Total rentals

    80 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    5.1K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore

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  5. Chicago
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