Holiday houses in South Side

4.92 out of 5 average rating, 71 reviews

Guesthouse in Chicago

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

4.75 out of 5 average rating, 327 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

4.93 out of 5 average rating, 46 reviews

Guest suite in Chicago

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.

4.84 out of 5 average rating, 526 reviews

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

Superhost

Apartment in Berwyn

5 out of 5 average rating, 4 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

4.92 out of 5 average rating, 273 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top floor 2 bedroom 2 bathroom condo in Bronzeville. It has high ceilings with lots of natural light. The kitchen is fully equipped with everything you need to cook a delicious meal. Plus, there are many food options nearby. Enjoy a 15 minute walk to the lake front and Oakwood beach. Centrally located near downtown, Solider Field, Rate Field, Field Museum, The Art Institute of Chicago, Chinatown, Hyde Park, and plenty more!

Superhost

Guest suite in Chicago

4.84 out of 5 average rating, 293 reviews

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

4.82 out of 5 average rating, 22 reviews

Vintage Condo-Heart of Hyde Park

Vintage charm with a mixture of modern design. It’s clean, it’s quiet and and very cozy. Located one block from downtown Hyde Park. This studio unit is walking distance to numerous restaurants, hotels and stores. University of Chicago campus is nearby and take their shuttle bus one block away to get there quickly or to explore Hyde Park. Public transportation is also nearby approx. a half a block away.

5 out of 5 average rating, 15 reviews

Cozy In the Middle of Everything

Enjoy a stylish experience at this centrally-located place. About a mile from the University of Chicago. 10 Minutes to Downtown Chicago. 3 Blocks from the beach, walking, and bike trails. Near grocery stores and beloved Bronzeville Eateries. Right off Lake Shore Drive with access to all Chicago Expressways. This is the perfect spot to relax while you enjoy all that the City of Chicago has to offer.

Superhost

4.87 out of 5 average rating, 204 reviews

The Sweet!

Privacy and comfort without the hefty price tag. This sweet basement suite is perfect for the solo traveler or couple needing space to relax and recharge. It's located in the wonderfully diverse and convenient neighborhood of Bridgeport (in between Pilsen and Chinatown) on a friendly and peaceful street. Some of the best restaurants and bars are within just a few blocks!

Top Guest favourite

Condo in Chicago

4.97 out of 5 average rating, 807 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

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Other great holiday rentals in South Side

4.73 out of 5 average rating, 40 reviews

Bees Knees - Room 3

BernardoRating, 5 stars2 weeks ago

I really enjoyed my stay at this place and would definitely recommend it, especially for the value. It’s conveniently located near bus stops and small markets, which made getting around and grabbing essentials very easy. The host was always very responsive and helpful, which made the whole experience smoother. The apartment is well-equipped with many utensils—there were plates, glasses, a cooking area that worked well for meals, and even an iron and ironing board. It’s also relatively quiet, which was great for resting. There are a few minor details that could be improved, like a couple of broken light bulbs, some marks on the bathroom walls, and a creaky, uneven floor. I also missed having a few hooks in the bedroom. However, none of these were major issues or detracted from the overall quality of the stay. I would not recommend it for people with mobility issues due to the steep staircase, but all in all, a great place with excellent value and a very helpful host. Would stay again.

5 out of 5 average rating, 3 reviews

Chic co-living minutes from UofC campus

JasonRating, 5 stars1 week ago

I had an amazing stay, the room was clean and nice, everything was exactly as listed, the hosts communicated well and had prompt responses to my questions. A+, highly recommend!

4.88 out of 5 average rating, 48 reviews

Yellow Room - South Shore Bungalow

GavinRating, 5 stars1 week ago

What a lovely place to stay. Lady Delia showed us her turtles and had a beautiful cat. She was very friendly and talkative. She drove us to get bus passes when we didn’t know where to get them. Jeffrey jump was a convenient bus to get from her place to the city very quickly. The bathroom had the window creaked open which made it smell like the coast in the mornings. The house is a historic bungalow which gave it a very different look and feel from what I’m used to. Spent some beautiful morning strolls along the neighborhood and got to see the beautiful architecture in the city; overall was worth what we paid.

4.8 out of 5 average rating, 5 reviews

Confortable and affordable

Said OmarRating, 5 stars2 weeks ago

the stay with Eduardo was very peaceful , quite and relaxing. I enjoyed it alot...

4.57 out of 5 average rating, 37 reviews

Private room in Bridgeport. #4

InésRating, 5 stars3 weeks ago

Nice place to stay in a safe area. I would go back there for another stay in Chicago and I recommend it !

5 out of 5 average rating, 4 reviews

Up-scale co-living near UChicago | Unit 101 Room 5

KyleRating, 5 stars1 month ago

Couldn't have been easier for a quick in and out visit to UC!

5 out of 5 average rating, 3 reviews

Condo Living! 5 mins from UChicago/Obama Center

JanRating, 5 stars2 weeks ago

Very responsive hosts. Perfect place for what we wanted, which was budget friendly and being reasonably near family that we were visiting. We didn't use the kitchen, but it is well equipped, very clean, lots of room to store groceries for those who do want a place where they can cook. I loved the flower garden just down the street and the nearness to Washington Park where we heard many song birds and saw a mother duck with several ducklings.