
Bed and breakfast holiday rentals in North Side
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Top-rated bed and breakfast rentals in North Side
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness and more.
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Popular amenities for bed & breakfast rentals in North Side
Family-friendly bed & breakfast rentals

Lovely UofC Prof mansion great on campus location
The hosts were great, and the property is beautiful! Our room was very clean and felt very private.

Classy and Cozy home in Evanston
This is my new favorite!! Patricia and Joaquin were the best hosts, from their hospitality to sharing their beautiful home and a wonderful homemade breakfast. Honestly, I did not want to leave, and do hope to return.

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)
This is the best and most affordable place in Chicago. You won’t get a better deal in Airbnb. Sharing the bathroom is not a big deal when everything is clean and works properly.

Great Edgewater/Andersonville private suite
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!

Country Retreat, 2 Block walk to Metra Train
This country house is well located, quiet, off the beaten path, but easy to reach. The rooms are super clean and well appointed. The Hosts are very social and take great care and interest in their guests. They are great communicators, and appreciate all feedback. Best advice to potential guests....must like dogs and good conversation,( and movies). And coordinate plans closely with hosts to take advantage of their local tips and advice. and Respect for house rules will make for a smooth stay for everyone. Travelers can not go wrong choosing to stay with Laura and Mike, they were/are the best.

Classy and Cozy 2nd. Room
Patricia made me feel like a house guest, not just a customer. She and her husband welcomed me when I arrived, and I enjoyed talking with them. They even offered a wonderful home-cooked breakfast. Patricia has beautiful watercolor paintings that she made throughout the house. The location, at the end of a dead-end street, is very quiet. The neighborhood looked attractive and safe. I was able to walk to Northwestern in about 40 minutes, all on sidewalks, mostly in residential areas. Bus service is also available nearby.
Bed and breakfast rentals with breakfast

Romantic Queen Room in Boutique Wicker Park B&B
Everything was perfect! Enjoyed the room and breakfast. Staff was very friendly and helpful.

Historic campus U of C Prof. mansion, top location
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.

Historic campus house owned by U of C Prof
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!

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

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

Cloudgate Room, minutes to O'Hare in Safest Area
Fair value for the stay

Luxurious King Room in Boutique Wicker Park B&B
This place is the perfect spot. Nice and clean and the building admin that check you in are wonderful. Totally would come back again.

King Bed with Jet Tub
Nice chill spot
Bed and breakfast rentals with a patio

A Hammock in Green Bay
Great Stay, would recommend.

Wrigleyville Suites Room 1
Great location and super easy

Villa Dubois Guest House Room 1
I was in Chicago for the night, and this stay made me feel right at home! We had a BEAUTIFUL room, and all the shared spaces were spotless and well-designed. I will definitely come back to Chicago and book this unit again. Most comfortable mattress I've ever slept on as well.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- Wilmot Mountain Ski Resort
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Lincoln Park
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Brookfield Zoo
- Flossmoor Golf Club
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
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