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Vacation rentals with breakfast in South Side

Find and book unique accommodations with breakfast on Airbnb

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Popular amenities for South Side accommodations with breakfast

House rentals with breakfast

Superhost
Home in Chicago
4.86 out of 5 average rating, 65 reviews

◆◆◆ Work, Play, Eat | 5B/3BA Near Everything ◆◆◆

PhoolRating, 5 stars1 month ago
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!!!
Superhost
Home in Chicago
4.56 out of 5 average rating, 133 reviews

Huge 2 Story Home/7miles from Downtown Chicago!

Eric And StephRating, 5 stars4 months ago
once we got our feet on the ground since we’ve never been to Chicago, it was an outstanding time in the windy city. The dining and living rooms are open to each other and we were able to be together as a family of 7!!! We cooked 2 of our meals each day at the bnb and simply had an amazing family time!!! ty to Kelvin for putting up with all my questions !!!
Guest favourite
Home in Chicago
4.99 out of 5 average rating, 79 reviews

Luxe SFH Bucktown Retreat with Garage Parking

JacquieRating, 5 stars3 months ago
The home was beautiful, clean, easily accessible and located in a great area. We had many options for restaurants within a few minutes drive. Easy access to downtown for exploring. Very comfortable amenities and well stocked kitchen. We would stay here again!
Superhost
Home in Bolingbrook
4.73 out of 5 average rating, 22 reviews

Private 3BR w/ Backyard | LCP Collection

CarltonRating, 5 stars9 months ago
this was a great place lovely 😍 will book again and who ever reading this should book to
Superhost
Home in Chicago
4.82 out of 5 average rating, 11 reviews

Cozy 4-Bedroom House with Patio

RodrigoRating, 5 stars6 months ago
Tudo perfeito, Thatheu é um excelente anfitrião, sempre responde rapidamente, a acomodação é perfeita, com uma estrutura excelente e a localização é muito boa, pois tem ônibus e uma estação de metrô bem pertinho que leva ao aeroporto e também para os principais pontos turísticos da cidade. Thatheu deixou água, leite e outras coisinhas, super gentil. O bairro é muito tranquilo, com boa estrutura de restaurante, mercado, lavanderia, dollar tree…
Guest favourite
Home in Westmont
4.89 out of 5 average rating, 84 reviews

Pretty Westmont Cottage & enclosed yard fenced.

PeterRating, 5 stars2 days ago
Attentive host who still respected our privacy. Nice co,y place in a great location/neighborhood
Superhost
Home in Gary
4.91 out of 5 average rating, 74 reviews

Laurna Dune

DnaiyaRating, 5 stars1 month ago
I had a great stay at this Airbnb! The place was clean, cozy, and exactly as described. Angela was super responsive and made sure I had everything I needed. The only minor issue was the water pressure and temperature in the sinks, but the shower worked perfectly, so it wasn’t a big deal. Overall, this is an amazing place to stay in Gary, Indiana, and I would definitely book again!
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 70 reviews

Spacious Retreat 7 Bed Oasis with 5 Baths, Hot Tub

MauroRating, 5 stars1 month ago
Patty's apartment is just perfect for big groups of people. We were 8. Beautiful, wide, and it's got everything you might need. Patty was always ready to accommodate any request and help us. we'd definitely go back!

Apartment rentals with breakfast

Top guest favourite
Apartment in Chicago
4.79 out of 5 average rating, 295 reviews

Cozy Garden-Subterranean Apartment

SusannaRating, 5 stars1 week ago
Wir hatten einen sehr schönen Aufenthalt bei Jenny. Die Wohnung hatte alles, was man braucht. Man kommt bequem mit den Öffentlichen Verkehrsmitteln in die Innenstadt und zum Flughafen. In der Nähe ist ein Supermarkt und die Gegend ist schön und ruhig.
Guest favourite
Apartment in Stickney
4.86 out of 5 average rating, 14 reviews

Near Midway Chicago- B & B

MarioRating, 5 stars2 months ago
Our stay here was an amazing experience! Would definitely stay here again! The area is very safe! The location felt like home! And so close to Chicago downtown. It was clean and met all of our standards! Alex was very friendly and always checking in on us to see if we needed anything else and made sure we were comfortable. The home had all the things we needed for a comfortable stay. Highly recommend this place for anybody that’s looking for a location close to downtown but still have that quietness away from the noisy city.
Guest favourite
Apartment in Whiting
4.97 out of 5 average rating, 101 reviews

The "Nest", unconventionally modern yet vintage.

CliveRating, 5 stars2 weeks ago
Felt right at home, right away. Love the mood of the place, beautiful decoration, cozy spaces throughout. My wife loved the soaker tub, melted her stresses away. Always found street parking right in front of the apartment each evening. Smooth trip into Chicago whenever the mood struck us. The mattress is definitely firm. If that suits you and your back, you are going to love this spot like we did!
Superhost
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Family-Friendly 4BR in Lincoln Park, Safe Area

CathyRating, 5 stars3 weeks ago
We had a great stay. Very safe location and in walking distance to many places. The unit was very clean and had enough room for all of us. We liked that there was a fitness center that we could use. Our host was very responsive and friendly. We would happily rent from them again.
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 170 reviews

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

NicoleRating, 5 stars5 months ago
Absolutely loved staying at Simida’s place! It was stunningly decorated with such attention to detail, making it both stylish and cozy. The space was spotless and incredibly comfortable, providing a true home-away-from-home experience. Located in an ideal spot, it was easy to explore the area while also enjoying a peaceful retreat. Can’t wait to book again – this is a gem I’ll keep coming back to! Five stars all the way! ⭐️
Top guest favourite
Apartment in Blue Island
4.94 out of 5 average rating, 293 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

JosephRating, 5 stars3 weeks ago
Carol and Dennis were great hosts with a beautiful home! They were very responsive and made sure we had everything we need. The neighbor has lots of charm and character as well, and felt completely safe. Highly recommended!
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 166 reviews

Heart of Wicker Park! Location. Walk to Everything

VictoriaRating, 5 stars1 month ago
The apartment is in a great location. There are many amazing walkable bars and restaurants. Then mostly a 15 minute Uber ride to areas like the bean, The Aquarium and so forth.
Top guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 294 reviews

The Garden on Wayne

SeanRating, 5 stars4 days ago
We had a wonderful first family trip to Chicago, and staying at Erin's place made it even better. The home was spotless and exactly as described. Erin went above and beyond by baby-proofing the outlets for our toddler and thoughtfully setting out toys and books to keep him entertained—such a kind and personal touch. The location is fantastic—right in Wrigleyville and within walking distance to Wrigley Field, great restaurants, and shops. I highly recommend this spot to anyone looking for a comfortable, family-friendly stay in a super convenient area.

Bed and breakfast rentals with breakfast

Private room in Winfield
4.95 out of 5 average rating, 62 reviews

Country Retreat, 2 Block walk to Metra Train

TroyRating, 5 stars67 months ago
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.
Private room in Chicago
4.85 out of 5 average rating, 356 reviews

Large private room w/ shared bathroom in Boystown!

GraceRating, 5 stars2 weeks ago
We enjoyed our last minute booking at The Villa Toscana! The house was a cool, eclectic space and located in Boystown, a bustling neighborhood with lots to do and see within walking distance from the house. Having a sink in the room was really nice, since the upstairs rooms all share one bathroom (as is detailed in the listing), and they provided a nice variety of breakfast items, which was above and beyond. Thanks Ashley!
Top guest favourite
Private room in Chicago
5 out of 5 average rating, 113 reviews

Urban Oasis Pilsen - guest room in townhouse

InhyeokRating, 5 stars1 month ago
Their accommodation is definitely the best Airbnb I've ever visited. The cleanliness, facilities, host, everything was superb. From start to finish, they were always so kind to me. I will never forget them, and if I visit Chicago again, I will definitely stay at their Airbnb. 정말 감사했습니다. 하나부터 열까지 모든 것을 다 디테일하게 챙겨주었고 숙소는 말할 것도 없이 너무 최고였어요. 위치도 좋았어요. 호스트들에게 너무나도 감사하며 항상 그들이 행복했으면 좋겠어요. 언젠가 다시 방문할 날만을 기다리고 있을게요. 다시 한번 정말 최고의 시설, 최고의 호스트가 맞물러진 최고의 숙소였어요.
Superhost
Hotel room in Chicago
4.85 out of 5 average rating, 48 reviews

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

JeanRating, 5 stars5 months ago
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.
Guest favourite
Private room in Chicago
4.77 out of 5 average rating, 318 reviews

Chicago River Room near USMLE

JessicaRating, 5 stars1 month ago
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.
Top guest favourite
Private room in Evanston
4.97 out of 5 average rating, 572 reviews

Classy and Cozy home in Evanston

KathleenRating, 5 stars3 days ago
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.
Private room in Westmont
3.33 out of 5 average rating, 3 reviews

King Bed with Jet Tub

LartezRating, 5 stars1 month ago
Nice chill spot
Guest favourite
Private room in Elgin
5 out of 5 average rating, 19 reviews

Ashiana #4 Bedroom/full bath in a 100 yr old home

AlejandraRating, 5 stars4 months ago
Nazneen and Mehtab went above and beyond to make my stay exceptional! I was a long-term guest while finishing my travel nursing contract, and this home was the perfect location for my commute to the hospital. The house itself is like an art museum. It’s full of color, charm, and rich with history. During my stay, I had the pleasure of creating several unique items with Nazneen’s Pursenality Specialty Handbags, which added a special, creative touch to my experience. Another thing I loved was the sound of the train in the distance. It was very cozy and helped me sleep better at night. This stay made my final weeks in Elgin truly enjoyable, and I would gladly return in the future! Thank you for treating me so kindly and opening your beautiful home. Even when I was sick towards the end, I felt so taken cared of with the hot teas you both made for me. Also, your cooking and food is so delicious. I left inspired to cook more after the meals we shared. Thank you so very much:)

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