
Bed and breakfast vacation rentals in North Side
Find and book unique bed and breakfast rentals on Airbnb
Top-rated bed and breakfast rentals in North Side
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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

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

(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).

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

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.

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.

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

Queen Bed with Private Bath 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

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."

Wrigleyville Suites Room 1
Wrigleyville Suites are 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 Cubs Stadium. Room 1 is a private room with a queen bed and shared bathroom for up to 2 guests. It is one of our largest and brightest room.

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.

Classy and Cozy 2nd. Room
2nd. Room available quiet suburban Evanston close to dowontown. Comfortable for two. Bathroom, full bed, closet, chests. street parking always available. Original art, books, Old World decor, wifi, personalized attention, delicious hearty breakfast. We are Covid-19 compliant and fully vaccinated.
Popular amenities for North Side bed and breakfast rentals
Family-friendly bed and breakfast rentals

Private room with private entrance in Boystown

Bright Room with a Garden View

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

(BR#1) Welcoming, warm & comfortable, 3 guests

SuperHost with Private bedroom/bath/entry Lakeview
Bed and breakfast rentals with breakfast

Cute room in downtown Boystown

Private room with private entrance in Boystown

Historic campus U of C Prof. mansion, top location

Queen Bed with Private Bathroom in Boystown

Historic campus house owned by U of C Prof

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

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

Luxurious King Room in Boutique Wicker Park B&B
Other bed and breakfast vacation rentals

Private room with private entrance in Boystown

Bright Room with a Garden View

Great Edgewater/Andersonville private suite

Large private room w/ shared bathroom in Boystown!

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

Cozy Garden Room in the middle of Boystown!

(BR#1) Welcoming, warm & comfortable, 3 guests
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