
Bed and breakfast vacation rentals in North Side
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts 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

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

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

Private Guest Suite • Sleeps 4 • Separate Entrance
⭐ Private walkout entrance ⭐ 1000 sq ft private guest suite ⭐ Fenced backyard + patio + fire pit ⭐ Pet friendly ⭐ Free driveway parking Welcome to beautiful Lake Zurich! This 1000 sqft walkout awaits you. The fenced yard makes it a pleasure to welcome your furry family members too. Whether you are here for an adventure or business, a couple, family, or a group of friends -please enjoy your stay! ✨ Our space is best suited for guests looking for a comfortable, quiet, and relaxing stay!

(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).

Cute room in downtown 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

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

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.

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.

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.

Cloudgate Room, minutes to O'Hare in Safest Area
My other listing can be found through my profile. This room is just next to the washroom. My place is only 1 mile/1.6km to USMLE Center; 10 minutes driving to O'Hare, 0.6 miles to CTA Blue Line station. Early check in is available for an additional fee. Prices are subject to change.
Popular amenities for North Side bed and breakfasts
Family-friendly bed and breakfasts

Private room with private entrance in Boystown

Cute room in downtown Boystown

Historic campus U of C Prof. mansion, top location

Bright Room with a Garden View

Large private room w/ shared bathroom in Boystown!

Cozy Garden Room in the middle of Boystown!

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

Private Guest Suite • Sleeps 4 • Separate Entrance
Bed and breakfast rentals with breakfast

Private room with private entrance in Boystown

Queen Bed with Private Bathroom in Boystown

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

Cozy Garden Room in the middle of Boystown!

Peaceful King Room in Boutique Wicker Park B&B

Top location, sunny UofC Prof on campus home
Other bed and breakfast vacation rentals

Private room with private entrance in Boystown

Cute room in downtown Boystown

Historic campus U of C Prof. mansion, top location

Bright Room with a Garden View

Large private room w/ shared bathroom in Boystown!

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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