
Holiday rentals with breakfast in South Side
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Top-rated Holiday Accommodation 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 Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

Kayaker’s Dune Cottage
This was a great kid friendly place to stay. Michael's dad brings fresh baked muffins. There is access to a water way in the back yard and across the street a beautiful trail to the dunes. Lots of games and things to do in the house.

◆◆◆ 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!
My family and I enjoyed our stay, if you can look past the neighborhood(that wasn’t extremely bad) it was a very welcoming stay. I would book with Kevin for future visits

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
Wonderful stay. Angela’s place was very welcoming, clean, and had everything we needed and more. The beds were super comfortable we slept just as well as we do at home. Check in and check out was incredibly smooth and we would definitely stay here again. Highly recommend if you’re visiting Gary!
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.

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
Enjoyed my getaway at this beautiful airbnb! Very clean and cozy. Simida was very friendly and her place made me feel right at home! Good and peaceful area, and plentiful street parking- definitely recommend!

Charming Unique 2 Bdrm Apartment in Victorian Home
This was our 3rd stay at this lovely Victorian apartment. The Blue Island location is perfect, whether driving into the city or to our daughter's place in a nearby suburb. My husband loves walking in this historic neighborhood. Carol is extremely responsive and flexible, when possible. The kitchen is stocked with breakfast items and a variety of snacks. We love the second story apartment, which is spacious and comfortable. Highly recommend!

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.

HUGE Hyde Park Modern Duplex
Bee was a great host. Home is definitely worth what I paid, it’s a home-away from home. Clean and smelled great! I would recommend this place.

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

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)
This is the best and most affordable place in Chicago. You won’t get a better deal in Airbnb. Sharing the bathroom is not a big deal when everything is clean and works properly.

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
Fantastisk husvert som var profesjonelle, og svært hyggelige. Husen ar meget rent, med alle fasiliteter. Stilte alltid opp for å sørge for at jeg fikk det beste ut av dagen, og kom med mange gode anbefalinger. Huset var fantastisk rent, og ryddig, hadde en super beliggenhet, med gratis parkering. Husverten og mannen hennes var utrolig snille, og lagde daglig frokost og middag til meg etter eget ønske. Anbefales til alle som skal besøke Evanston, og her vil jeg leie neste anledning jeg er på reise til Evanston.

King Bed with Jet Tub
Nice chill spot
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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 Zoo
- Lincoln Park
- 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