
Vacation rentals with breakfast in South Side
Find and book unique accommodations with breakfast on Airbnb
Top-rated accommodations with breakfast in South Side
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.
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Popular amenities for South Side accommodations with breakfast
House rentals with breakfast

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

Huge 2 Story Home/7miles from Downtown Chicago!
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 !!!

Luxe SFH Bucktown Retreat with Garage Parking
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!

Private 3BR w/ Backyard | LCP Collection
this was a great place lovely 😍 will book again and who ever reading this should book to

Cozy 4-Bedroom House with Patio
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…

Pretty Westmont Cottage & enclosed yard fenced.
Attentive host who still respected our privacy. Nice co,y place in a great location/neighborhood

Laurna Dune
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!

Spacious Retreat 7 Bed Oasis with 5 Baths, Hot Tub
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

Cozy Garden-Subterranean Apartment
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.

Near Midway Chicago- B & B
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.

The "Nest", unconventionally modern yet vintage.
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!

Family-Friendly 4BR in Lincoln Park, Safe Area
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.

Decompress on a Sophisticated Chaise at a Glamorous Hideaway
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! ⭐️

Charming Unique 2 Bdrm Apartment in Victorian Home
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!

Heart of Wicker Park! Location. Walk to Everything
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.

The Garden on Wayne
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

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.

Large private room w/ shared bathroom in Boystown!
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!

Urban Oasis Pilsen - guest room in townhouse
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.

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.

Chicago River Room near USMLE
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.

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.

King Bed with Jet Tub
Nice chill spot

Ashiana #4 Bedroom/full bath in a 100 yr old home
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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- 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
- The Field Museum
- Wicker Park
- Lincoln Park
- Lincoln Park Zoo
- 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
- Chicago Cultural Center