Holiday rentals with breakfast in South Side

This place was spacious and worked great for our group in town for a concert. There was plenty of room and privacy, the beds were comfortable, the water was hot, and the garage fit two SUVs. Having separate bathrooms was the plus for us, and well worth it. While the neighborhood isn’t the quietest — we heard neighbors yelling at night and in the morning — this was clearly stated in the listing, and we still felt safe throughout our stay. The location was a 15-minute drive to Soldier Field, which was super convenient. Just be prepared for Chicago traffic — since the home is far enough from downtown that the subway isn’t really practical, driving is your best bet, but it can double your commute time depending on traffic.

FANTASTIC!! Great host! Awesome location! Clean house with everything needed available.. my kids loved the house, it felt like home away from home. Peaceful … Wish I could give more stars than 5!!!

Dawn is definitely a Super Host her airbnb is exactly like the title, Classic Charm with Modern Flair, guests will not be disappointed , from the time you walk through the door until checkout, you'l feel you're in a 5-star hotel, but at home, it was roomy the beds(queen sized) in every room with hotel style linen amenities such as appliances which included washer and dryer and hair dryer, a sun room with games for children and family, TVs in every room except dining and fully equipped kitchen quality dining ware, I'm sure this summer will be booked full because there will be a great outdoor area to enjoy, bottom line I hope next time I visit my Chicago family, she will have availability, Dawn, Thank you !

My family and I rented Kevin's place for my niece's wedding. we enjoyed ourselves and the accommodations. Kevin was super responsive and made us feel welcome. the neighborhood is isolated but peaceful.

Perfect place to stay for our visit to Chicago with friends! There was ample room in the BnB for all of us, including a spacious dining and living room. The kitchen was very well stocked including coffee, juice, eggs, and toast for us to make our own breakfast (a welcome surprise!). It was very walkable to transit, with a CTA Blue Line station nearby. Thatheu was very responsive and check in was straightforward. Also the later check-out time was very convenient as we were able to take the time for breakfast before heading out for the day. Thanks again for helping us to have a great trip!

We had a wonderful experience staying at the Chic Cottage and would recommend it to any one looking for a comfortable home away from home place , available at a great price and good sub urban location with Super Markets and restaurants close by .

We had a wonderful stay at this property, it truly felt like a home away from home. The entire place was exceptionally clean, and the kitchen and dining area were spacious and easy to move around in. Both bedrooms were spotless, and the mattresses were incredibly comfortable. If you’re looking for a quiet, private place to stay, this is the perfect choice. I would definitely stay here again! 😊

We rented this for a two night stay to attend a couple of Cubs games! You can’t beat the location!! Def go as early as you can before if it’s game day parking and getting through to the property was a beast because we arrived later than we planned.

Perfect spot for 2, more spacious than expected for a 3rd floor apt. Easy, clear instructions when viewing the listing and inside the apt

T was a great host from start till finish. Very responsive when we had questions. The place it self is a gem. The nostalgic decor was a dope. I would definitely recommend this for anyone visit Chicago.

DW was very flexible and responsive. He was very accommodating to allow us to check in early and flexibility on check out as well. The location is good - if you are super sensitive to the noise of the train it may not be ideal, but the proximity to the train stop and Wicker Park was great. You must go to Mindy’s bakery - if I lived this close to a place like that I would gain so much weight 😅. Thanks again!

It was a nice place. Had everything needed. The locality is really good. Quiet, peaceful and nice people.

The house was comfortable and spacious

We were there attending an UChicago graduation, and the place is in a great location for that. The beds were very comfortable, and the apartment is very spacious. The street is nice and quiet. We were glad that they had Kcups available for the Keurig before we head out super early on the Convocation day, as we are coffee drinkers. All the bathrooms had toiletries in the shower, which is always a plus. We enjoyed Bee’s place and would book it again when needed.

One of the best Airbnb's we have stayed in. The location is great with excellent bars and restaurants nearby, but in a quiet street. The accommodation is as advertised, but also includes everything you need for cooking and generally relaxing. I wouldn't hesitate to recommend this place and if we come to Chicago again I would definitely try and stay here

Great location nice view amazing host

You get exactly what you look for. The location is awesome and I found parking immediately. Great place

I recently had the pleasure of staying at Christiane's & Patrick’s beautiful home, and I can't recommend it highly enough! From the moment I arrived, I felt welcomed and at home. The space is impeccably clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. Both were outstanding host—responsive, friendly, and full of great local recommendations. They went above and beyond to ensure my stay was perfect, checking in to make sure I had everything I needed.

Very cozy place in a calm tucked away neighborhood. Would definitely stay again!

Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.

Nidhi’s place was exactly as described. I can’t say enough good things about it. The bed was very comfortable. The Jacuzzi and mood lighting was fun. The dorm size fridge and microwave wow you don’t normally see that in a motel anymore. Everything was clean and the water pressure was very good. Plenty of hot water.. I was shocked that every morning a full complete breakfast was in the lobby for free not to mention 24 hour coffee! We were there on a business trip and across the street were excellent restaurants, including an upscale bar with delicious meals, a sushi house, Chinese restaurant and a diner. You could also get your nails done and book a massage right across the street. I enjoyed taking the train into Chicago. It was very simple to buy your ticket on the spot not far from the motel at the station. The neighborhoods surrounding her place were beautiful. I did a lot of walking and there were sidewalks everywhere making it safe. She and the check-in managers we’re friendly.

My adult daughters had a lovely stay in your home. Your breakfasts got rave reviews. Your spot was the perfect location for them to attend the graduation and events at Northwestern. Thank you for opening up your home and being such friendly and helpful hosts!

I always enjoy stays at the Hamlin House and this was no exception! The Blue Room is lovely, - spacious with gorgeous windows and a spa-like bathroom. Wish I could have stayed longer!

Great communication and a comfortable stay!