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Vacation rentals with breakfast in South Side

Find and book unique breakfast rentals on Airbnb

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Popular amenities for South Side breakfast rentals

House rentals with breakfast

Guest favorite
Home in Gary
4.95 out of 5 average rating, 173 reviews

Kayaker's Dune Cottage

MariRating, 5 stars1 month ago
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.
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 stars3 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 favorite
Home in Chicago
4.99 out of 5 average rating, 78 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

GaryRating, 5 stars4 months ago
One of the best host we have ever stayed with!!
Guest favorite
Home in Westmont
4.89 out of 5 average rating, 83 reviews

Pretty Westmont Cottage & enclosed yard fenced.

MatthewRating, 5 stars2 months ago
Cozy little house, an easy drive from downtown westmont restaurants. Neat and well kept, though appliances felt a bit cheap (still worked perfectly fine and we're clean)
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!

Apartment rentals with breakfast

Top guest favorite
Apartment in Chicago
4.79 out of 5 average rating, 294 reviews

Cozy Garden-Subterranean Apartment

MorganRating, 5 stars2 weeks ago
Jenny went above and beyond! She was super communicative & very friendly. She even let me check in before checkin time, which I greatly appreciated. The apartment has literally everything you need. All the little details and small things you could want, are there. I would highly recommend staying here for a longer extent of time, as you would feel as if you’re in your own home.
Guest favorite
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.
Superhost
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!
Guest favorite
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 favorite
Apartment in Blue Island
4.94 out of 5 average rating, 293 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

JosephRating, 5 stars2 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!
Superhost
Apartment in Chicago
4.89 out of 5 average rating, 54 reviews

Modern Retro 90s Themed 3bd Low Cleaning fee!

MadiRating, 5 stars7 months ago
Overall, this place was spacious, clean, loved the theme, easy to get in and out, there were two separate doors you could lock once inside, and it was way larger than what I was expecting. Love the open floor plan, felt safer knowing that the hosts lived on the premises, as the neighborhood/location was a bit questionable. Had no problems though, and would definitely recommend as long as you’re okay with going out of the way for gas, food, etc!
Guest favorite
Apartment in Chicago
4.92 out of 5 average rating, 36 reviews

HUGE Hyde Park Modern Duplex

ThomasRating, 5 stars3 months ago
This was a great experience 5 star air bnb I will come here again and again the host makes you feel at home.. The house was easy to find very clean a overall 5 star experience
Top guest favorite
Apartment in Chicago
4.97 out of 5 average rating, 293 reviews

The Garden on Wayne

JimRating, 5 stars1 week ago
We really liked this place! A hidden jem. It's in a really nice, convenient location in a safe quiet area and is a comfortable homey quiet space. As a longtime landlord, I can tell that the owner has given a lot of thought and takes pride in presenting a well thought out, well-stocked place. It has a good selection of needed kitchen implements & equipment, with extra stuff that is seldom available elsewhere but always needed ( e.g., tupperware and ziploc bags...nice!). Provision of the little things (butter, creamer for coffee, eggs, soft drinks, beer, water, jellies/jams and homemade banana bread and more) so you don't have to immediately go grocery shopping. A perfect selection of spices needed for basic cooking. A nice quiet backyard with your own shady spot for morning coffee, a convenient location not far from the "L", this place is one of my favorites and I hope we can stay here again.

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, 355 reviews

Large private room w/ shared bathroom in Boystown!

JerriRating, 5 stars6 months ago
Great place to stay! Super cute, everyone was friendly, the place was quiet, and the breakfast was top notch! The neighborhood is super cute and all the locations were walkable. Parking was a breeze even for a Friday afternoon. Will def be staying here again if we find ourselves in the area!
Top guest favorite
Private room in Chicago
5 out of 5 average rating, 113 reviews

Urban Oasis Pilsen - guest room in townhouse

SydneyRating, 5 stars2 weeks ago
We had a great time staying here. Christiane and her husband are both very gracious hosts - they had breakfast available for us every morning & made us feel right at home.
Superhost
Private room in Chicago
4.78 out of 5 average rating, 266 reviews

Cloudgate Room, minutes to O'Hare in Safest Area

Vinod KumarRating, 5 stars7 months ago
Fair value for the stay
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 favorite
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 favorite
Private room in Evanston
4.97 out of 5 average rating, 572 reviews

Classy and Cozy home in Evanston

KathleenRating, 5 starstoday
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

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