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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent North Side reviews

  • Perfect!

    "My family needed a place to stay in Chicago for a wedding. There were 7 adults and 4 children. The Chicago Guest House fulfilled all of our needs and more! When we arrived there was a crib, highchair, and baby gate, for the stairs, waiting for us! The home is so well equipped and clean that we wanted for nothing. It's location was perfect for us. Walking distance to the grocery store, drug store, cute shops, and restaurants. Teri was a pleasure to work with. Always so friendly and on top of everything! Thank you Chicago Guest House! We hope to return some day."
    Guest: Kathy I. Date of Stay: October 2014 Review Submitted: October 17, 2014
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  • Wonderful baseball getaway

    "My husband, the boys and I had the pleasure of staying in this wonderful home for a few days while catching some Yankees/Cubs baseball. The Roscoe Village location was so quaint and quiet with its tree-lined streets, not to mention the Brown line was conveniently close! We loved the restaurants for brunch that were just a block away. Kim was always accessible and very accommodating to our special requests during our stay. We especially enjoyed the experience of being together watching television or sitting on the spacious deck with no interruptions of a busy hotel. Comfortable beds plus an abundance of towels made for a homey and relaxing feel. The furniture and décor was exactly to our taste and the upscale kitchen is fantastic if planning to cook and congregate there. Most important to us, was a washer/dryer on-site to launder our clothes after getting soaked while walking back after a ballgame. I usually have good luck with VRBO and this fantastic experience will keep me coming back!"
    Guest: The Hendricksons Date of Stay: May 2014 Review Submitted: May 25, 2014
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  • Delightful!

    "What a wonderful discovery! My wife and I stayed here during Christmas week with our adult daughter, visiting two sides of the family. This was the perfect home base and getaway from too much festivities. The carriage house has a unique charm and is very comfortable. Cynthia was a generous host, but gave us total privacy too. The neighborhood is quiet but close to everything. Next visit to Chicago, this will be my first choice."
    Guest: Philip M. Date of Stay: December 2013 Review Submitted: January 19, 2014
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  • Fabulous 2-level condo in wonderful neighborhood!

    "Love the no-key entry, which made it very easy for multiple guests arriving at different times to gain entry. The apartment was fresh and clean with lovely music playing when we arrived. The apartment was beautiful, spotless and well located, and unlike many other VRBO or airBNB places, we didn't have to provide annoying necessities like toilet paper and paper towels and trash bags. The owners also take care of stripping beds and laundering towels, etc, so it really was 5-star service! This was really a great feature since we were staying for just the weekend and didn't want to have to deal with these things. It made it like a hotel stay but with the warmth and comfort of a home. Without reservation, I would definitely stay here again and will be calling next time we are going to Chicago with a group!"
    Guest: Amy M. Date of Stay: October 2014 Review Submitted: October 10, 2014
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