Bed and breakfast holiday 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.

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Guest favourite

Room in Wilmette

4.95 out of 5 average rating, 220 reviews

(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.) 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. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).

Room in Evanston

4.67 out of 5 average rating, 66 reviews

Huge (2Beds) 1 Bedroom

Enjoy the glamour of this stylish, upscale place. 2 Beds (Queen+Full) in this bedroom. You’ll love the stylish decor of this charming place to stay. Working / computer table with walking closet. Free Breakfast and Wi-Fi. Just 1.5-2 miles from Downtown Evanston and Northwestern University, you are a straight shot from countless dining, shopping, & entertainment options. Close to Downtown Chicago. Bus station is walking distance which connects you all around Chicago. Beaches are about 3.5 miles

Guest favourite

Room in Chicago

4.95 out of 5 average rating, 100 reviews

Top location, sunny UofC Prof on campus home

NO closer accommodation to the U of c campus, large wrap around deck with garden and small semi private deck. convenient access to lakefront, Obama house, Science and Industry museum, public transport. Excellent do it yourself morning breakfast in large kitchen, sparkling clean home. Newly renovated room, marble bathroom floors. More like a traditional bed and breakfast than airbnb. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Guest favourite

Room in Palatine

4.93 out of 5 average rating, 188 reviews

Quiet Primary King Bed, Kitchen & Private Bathroom

Primary bedroom in a quiet house. So many amenities. Welcome long-term stay. Sorry for security and safety reasons, we don't show in advance of booking. * The closest deal 2 miles to #Renaissance #Convention Ctr * We may now offer a great discount for your specific dates * Self-check-in whenever, in safe & great area with all free parking * Private in-room bathroom with WiFi - Close to dozens of restaurants - A mile to all highways: IL53, I90 & I355, I290 - 15 min O'Hare Intl Airport

Guest favourite

Room in Chicago

5.0 out of 5 average rating, 88 reviews

Urban Oasis Pilsen - guest room in townhouse

A walk-up in Chicago's coolest neighborhood - Pilsen! Your private bedroom has a queen-size bed and an en-suite bathroom with a tub/shower combo. There is a small desk, ample storage space, and a TV with streaming services. While your many triple-paned windows let in light, air, and sunshine, you will also hear the I-90/94 nearby. Please note that your room is on the third floor of the building (40 steps). On the second floor, you'll find (y)our kitchen, living rooms, TV den, and balcony.

Guest favourite

Room in Chicago

4.94 out of 5 average rating, 218 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

Guest favourite

Room in Chicago

4.9 out of 5 average rating, 80 reviews

Serene place with the garden. Free parking.

I live in Albany Park, Chicago. It's quiet, family oriented, with lots of parks and treelined streets. The Chicago River Trail is within walking distance too. My home is a charming 2 flat building, built in 1909. It has lots of original, unique details. My home is a tranquil and peaceful place. My decor mainly consists of hand-made furniture, artwork, crystals, wind chimes, etc. I don't use any chemical cleaning supplies, I use only home-made products and essential oils.

Room in Chicago

4.77 out of 5 average rating, 364 reviews

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

Superhost

Room in Chicago

4.8 out of 5 average rating, 302 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, Yoga, Gym, Movie Theater, Multiple Bars & Diverse Cuisine within 5-15 min walking

Guest favourite

Room in Chicago

4.9 out of 5 average rating, 316 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access, use of entire level including 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."

Room in Chicago

4.75 out of 5 average rating, 296 reviews

Chicago River Room near USMLE

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.

Guest favourite

Hotel room in Chicago

4.91 out of 5 average rating, 45 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.