Private suite vacation rentals in South Side

A cozy sleeping area features a neatly made bed with soft gray pillows and a decorative green bolster. A bedside lamp and a small plant add touches of comfort, while a piece of framed artwork hangs on the white wall above the bed.

4.99 out of 5 average rating, 123 reviews

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

A bright and airy living room features a mix of modern and natural elements. A low wooden table is set on a textured rug, accompanied by a comfortable gray sofa adorned with colorful pillows. A large window allows ample natural light, illuminating the space.

4.94 out of 5 average rating, 419 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

A well-kept garden features blooming white hydrangeas surrounded by lush greenery. In the background, a classic two-story house displays a spacious balcony and a pergola, providing a serene outdoor dining area. The peaceful setting is complemented by seating among the vibrant plants.

4.99 out of 5 average rating, 363 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

An armoire is seen against a wall, featuring open doors revealing a mini fridge and microwave. A neatly stacked assortment of towels is visible above the mini fridge. A doorway to a bathroom is located on the right, showing hints of modern fixtures.

4.92 out of 5 average rating, 138 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

A classic gray stone building is presented with elegant architecture, featuring large front steps leading to a wooden door. Lush greenery surrounds the entrance, with a wrought iron fence enclosing a well-maintained garden space at the front.

4.97 out of 5 average rating, 292 reviews

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

A spacious backyard features a wooden deck with a pink picnic table and two blue chairs. Flower beds and a fire pit are visible among the greenery. A grill and a small stone area are also included, surrounded by a privacy fence.

4.9 out of 5 average rating, 108 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

4.95 out of 5 average rating, 189 reviews

Casita Plzeň Guest Suite

Stay in the heart of one of the world’s coolest neighborhoods, as recognized by Forbes, in a Historic Chicago Worker’s Cottage from the 1800s. The Loop is just five stops away on the Pink Line. McCormick Place is a 20min trip, the hospital district is just 15 mins away, Soldier Field and the UC are a short Uber ride. The lakepath, only two miles from your doorstep. Experience Chicago like a local, with history, convenience, and adventure all in one unforgettable stay.

4.94 out of 5 average rating, 125 reviews

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

A foosball table is positioned in the foreground, featuring uniform rows of players. The players are crafted from black with gold accents, arranged to create a competitive atmosphere. Bright light filters in from a nearby doorway, illuminating the game area.

4.97 out of 5 average rating, 120 reviews

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

A well-lit hallway is lined with neutral-toned walls, leading to a carpeted area. Decorative wall sconces cast a soft glow, enhancing the inviting atmosphere. A visible staircase leads to the upper level, while the back of the hallway opens to a light-colored room equipped with a desk.

4.95 out of 5 average rating, 188 reviews

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

A well-lit hallway showcases exposed brick walls and polished wood flooring. A cozy seating area includes a spacious bed draped with a blanket, accompanied by a side table and lamp. A large television is mounted on the wall, while barn doors lead to another room.

4.91 out of 5 average rating, 120 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

A modern kitchenette is showcased, featuring a compact refrigerator and various coffee-making appliances. Colorful artwork is displayed above the counter, adding visual interest. Shelves hold decorative plants and kitchen essentials, with a sleek, wooden countertop and light-colored flooring enhancing the contemporary design.

4.91 out of 5 average rating, 147 reviews

New Bright & Airy Entire Unit in Logan

This new modern unit is located in West Logan, one of the most exciting neighborhoods in Chicago. Close to public transportation, 2 blocks from the 606 Bloomingdale recreation trail, and minutes away from the best restaurants and bars in the city! Wifi, large-screen TV with streaming channels, washer/dryer, kitchenette, mini fridge, coffee/tea, board games, free street parking. You will love this custom designed & converted space!

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Popular amenities for South Side private suite rentals

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Family-friendly private suite rentals

A welcoming sitting area features two upholstered chairs with footstools, each adorned with decorative pillows displaying a Chicago skyline design. A small table is situated between them, creating an inviting space for relaxation or conversation.

4.87 out of 5 average rating, 263 reviews

2 King Beds /Easy Downtown / Free Str Parking-Read

JaymeRating, 5 stars2 weeks ago

Beautiful home, and easy access to the house. With nice bars and easy transportation near by to the city. Michelle was a wonderful host, would stay here again.

4.98 out of 5 average rating, 256 reviews

The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.

Guest suite in Evanston

A guest suite centrally located, but so quiet

RobinRating, 5 stars1 week ago

We had a lovely stay at Cinda Jo’s home. One note: Be careful if you are tall, as ceilings are low. Otherwise, the attention to detail, decor, full kitchen with nice appliances and host provided croissants were all over the top wonderful. The space was cozy and warm, and felt like home. When we left Cinda Jo wanted to make sure all went well and we had a nice chat before taking off to the airport. Recommend highly.

A spacious backyard is depicted, featuring a well-maintained lawn framed by lush greenery and trees. A wooden deck attached to the house is visible, along with a fenced perimeter providing privacy. Sunshine illuminates the area, creating a peaceful outdoor space.

4.97 out of 5 average rating, 422 reviews

Private suite in Lincoln Square

TaylorRating, 5 stars1 week ago

Great location, nice space, helpful hosts - would stay again!

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.94 out of 5 average rating, 161 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

JasmineRating, 5 stars1 week ago

Jamie's place was absolutely adorable—just as pictured and described. The bedrooms were very nice, and the beds were super cozy. The kitchen was fully stocked with all the gadgets you’d need to prepare whatever you'd like, plus a few condiments, which was a nice touch. The bathroom was tidy and well-kept, with fresh, clean towels and linens provided. Jamie was more than welcoming and very accommodating to any requests. Even though she lives below the rental, she was incredibly respectful of our space—warm, friendly, and never intrusive. It truly felt like having my own little apartment. Overall, a wonderful place to stay, and I will definitely be returning.

A bright kitchen features orange walls and white cabinetry. A white refrigerator and a black gas stove are positioned alongside a kitchen sink. A small dining table with a checkered tablecloth is set for two. Colorful artwork and a floral curtain enhance the inviting space.

4.92 out of 5 average rating, 473 reviews

Cozy, Quiet, Garden Getaway!

LeahRating, 5 stars1 week ago

My girlfriend and I came into town from Milwaukee for an action-packed weekend. Having previously lived in a nearby neighborhood, everything came very natural to get around on the CTA. Beth has a very spacious and clean space. Went above and beyond with amenities. Felt right at home. The surrounding neighborhood has so much to do and beautiful scenery to take in. A wonderful space to spend a weekend or any occasion. Highly recommend! Can’t wait to return!

A spacious recreational area features a ping pong table, a large flat-screen TV, and comfortable leather seating. A coffee table sits in front of the couch adorned with a colorful quilt. Exercise weights are positioned on the floor, adding to the diverse amenities of the space.

4.85 out of 5 average rating, 253 reviews

Wrigleyville/Boystown/Entire Private Floor!

LisaRating, 5 stars5 days ago

On first impression, Steve's place seems a bit oddly laid out - the main bed is built over a jacuzzi tub and is basically in the bathroom next to a weight set. But once you got used to the setup, everything was amazing. His neighborhood is tree-lined and gorgeous and a quick safe walk to either the red line train or Wrigley. Parking is tricky especially late at night - I'd recommend parking your car and not moving it (which is easy to do because of the close proximity of the train). This was a great spot for seeing games at Wrigley and for accessing the downtown attractions and Sox games (which are also right off the red line). We stayed five days and had no issues getting anywhere we wanted to go. And Steve's place is a GREAT DEAL - the total cost of our 5 day stay was much cheaper than anywhere else we looked. Steve and his wife are super friendly as well....and the mattress was one of the comfiest I've ever slept on. We'd definitely stay again if we return to Chicago!

4.91 out of 5 average rating, 500 reviews

A modern kitchen showcases dark wood cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop extends into a bar area with three metal stools. A microwave and kettle are placed on the counter, illuminated by overhead lighting.

Guest suite in Wood Dale

The Deer Suite

AspenRating, 5 stars3 days ago

Honestly the entire stay was great! It my fiancé and I’s first Airbnb booked and scheduled alone. The stay was great and the scenery was beautiful.

A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.

4.96 out of 5 average rating, 344 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

MichelaRating, 5 stars1 week ago

Wonderful place to stay! Photos seriously don’t do it justice, the outdoor area is beautiful.

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Private suite rentals with a patio

4.95 out of 5 average rating, 21 reviews

The exterior shows a single-story house with a well-maintained lawn and a flagpole. A small patio with seating is visible in the foreground, inviting relaxation. Lush greenery and decorative landscaping enhance the inviting appearance of the property.

Guest suite in Joliet

Home Sweet Home

KayRating, 5 stars3 weeks ago

This was the perfect place to stay while attending a 5 day event close by. The location was perfect: safe, peaceful and convenient. Iris was friendly and in helpful communication from the start. She was available, responsive and flexible. I look forward to staying again and would recommend!

A cozy living area features a light-colored sofa adorned with a textured throw and a contemporary black-and-white artwork on the wall. A sleek kitchen island with two bar stools sits adjacent to the living space, illuminated by pendant lighting. Large windows provide a view of the outdoor greenery.

4.88 out of 5 average rating, 49 reviews

Comfy suite w/ steam shower near McCormick Place

AleshiaRating, 5 stars1 week ago

Felicia's place was fantastic! The location was perfect for our vacation with walkable access to the green line as well as quick access to major roads. The neighborhood was quiet and felt like home. Parking was never an issue. We would stay again!

A cozy living area features a gray couch adorned with blue and green cushions. A round coffee table sits in front of a flat-screen television. Wall art depicting tranquil landscapes enhances the space, while a wall clock indicates the time.

4.85 out of 5 average rating, 91 reviews

Comfortable and Cozy Suite in Quiet Neighborhood

KierraRating, 5 stars1 week ago

Perfect, Getaway vacation spot for my husband and I. Very peaceful. Felt just like home. 420 Friendly was most definitely a plus. Alexis was the perfect host, very responsive and very accommodating. We enjoyed the stay. Wish we could have stayed longer. Most definitely will be back whenever visiting Chicago.

An exterior view of a charming blue building with a staircase leading to the entrance. A spacious outdoor area features a large table surrounded by several chairs, complemented by surrounding greenery and decorative plants. Trash bins are located to one side.

4.85 out of 5 average rating, 13 reviews

The Hidden Beach House

SydneyRating, 5 stars1 week ago

This stay was peaceful, yet SO CLOSE to everything! My partner and I wanted a weekend getaway for his birthday, and this was the perfect place to stay. Lincoln park was a short walk away, yummy restaurants, and walking/uber distance to downtown like the Bean. The location was everything!!Caid was also very responsive which made the process stress-free.

A charming two-story home is framed by blooming pink trees. The front porch, adorned with flower pots, provides a welcoming entrance. White railings and steps lead up to the door, while an iron fence surrounds the lush front yard.

4.95 out of 5 average rating, 74 reviews

Logan Square’s Garden apt style rental

CandiceRating, 5 stars8 months ago

Desiree is a great host and is very friendly and welcoming. We were lucky to have found this spot.

The living room features two teal sofas arranged for comfort, complemented by a purple ottoman. Natural light filters through sheer curtains, illuminating the wood flooring. A small plant and framed artwork adorn the walls, enhancing the inviting atmosphere of the space.

4.84 out of 5 average rating, 69 reviews

Logan Square Chicago 2BR cottage, close to it all!

ConnorRating, 5 stars2 days ago

We loved this AirBnB, neighborhood, and host! Everything was clean and easy. The outdoor area and the couches were so cute. Elizabeth was proactive and thoughtful.

4.75 out of 5 average rating, 48 reviews

2BR Logan Sq Mini-Resort stay + Pet friendly

ShitakiaRating, 5 stars3 weeks ago

This Home Was So Beautiful The Host Was So Nice And Fun , I Will Love To Stay Again Book Here

A modern kitchen area includes sleek cabinetry and stainless steel appliances. A wooden dining table surrounded by black metal chairs invites shared meals. A colorful abstract artwork decorates the wall, adding visual interest to the space. Natural light streams through a nearby window.

5 out of 5 average rating, 4 reviews

ENC-Chi Arts Suite Near United Center & Downtown

AustinRating, 5 stars1 week ago

Kimberlie and Phil were wonderful hosts. They were responsive and communicative through the whole process. Our only disappointment was that we didn’t get to meet their fur baby!

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Private suite rentals with a washer and dryer

A modern kitchen features dark cabinetry with a spacious island topped with granite. Bright natural light enters through large windows, highlighting the sleek appliances. The open layout connects to the dining area with red chairs, complemented by ceiling fans and track lighting above.

4.98 out of 5 average rating, 50 reviews

2-Bedroom w/ Kitchen & Laundry

MartaRating, 5 stars1 week ago

It was our second time staying at this place. We came here again because we knew it’d be just perfect! Karina is a great host and the place is really well equipped with all you’d need for your stay. We have now found our place to stay in Chicago!

A clean bathroom features a dark cabinetry under a sleek sink, complemented by a wall mirror with a decorative frame. The light grey walls and marble-patterned floor contribute to a bright and spacious feel, with a door visible leading to another area.

4.93 out of 5 average rating, 14 reviews

1 bed 1 bath private living room

KyjaRating, 5 stars7 months ago

My two year old and I had a very pleasant stay. Elom was friendly and responsive. The space was comfortable and clean. The neighborhood was quiet and the neighbors were friendly.

4.88 out of 5 average rating, 104 reviews

A spacious living area features two comfortable leather sofas and a wooden coffee table. A dining area with a small table and four chairs is visible, along with a bookshelf displaying various items. Soft lighting and neutral walls contribute to an inviting ambiance.

Guest suite in Wheaton

Guest Suite by Wheaton College

DanaRating, 5 stars3 weeks ago

This was our second stay at Jennifer and Grant’s, and once again it was wonderful. Their home is quaint, cozy, and located in a beautiful neighborhood near Wheaton College. The rental is spacious, impeccably clean, and the kitchen was fully stocked with everything that we needed to prepare our meals. We truly enjoyed our time here and hope to return again soon. Thank you, Jennifer and Grant!

A modern bathroom is displayed, featuring a dark slate tile wall and a wooden countertop. A sleek black sink is positioned next to a traditional toilet. Soft lighting enhances the space, while a shower with a curtain and frosted window offers privacy.

4.88 out of 5 average rating, 382 reviews

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

RebeccaRating, 5 stars1 week ago

Had a wonderful and peaceful stay. Everything was super clean and just as described. Easy check in with clear instructions. Paul was very helpful with information to help us out during our stay. Highly recommend!!

An aerial view captures the vibrant cityscape, featuring a baseball stadium surrounded by a mix of residential and commercial buildings. The setting sun casts a warm glow over the horizon, seamlessly blending with the lake in the distance.

4.95 out of 5 average rating, 209 reviews

1 mile from Wrigley Field

AprilRating, 5 stars4 weeks ago

Loved staying here! Great location, price and Kelly is a very responsive host. Will definitely book again!

4.87 out of 5 average rating, 181 reviews

A modern coffee station is presented with a sleek Keurig coffee maker, positioned next to a wooden tray containing various coffee pods and sweeteners. A paper towel holder stands nearby, complementing the minimalistic kitchen design featuring a marble countertop and clean lines.

Guest suite in Skokie

Adorable studio style unit - Self check in ⚡️

Venkata Bhanu AkshayRating, 5 stars6 months ago

Everything in the unit is absolutely fine, just bring your body wash and lotion and relax

A cozy nautical-themed bedroom is presented, featuring a spacious bed adorned with blue and white linens. A round mirror with an anchor motif is mounted on the wall. A light-colored accent chair and a small table complement the room's decor, while an ensuite bathroom is visible through an open door.

4.93 out of 5 average rating, 219 reviews

Lincoln Square In-laws Suite: Private Entrance

EmilyRating, 5 stars3 weeks ago

Axel's place was fantastic! My husband and I stayed here for a quick weekend getaway to visit friends and family. The neighborhood is gorgeous, quiet, and safe, and very close to coffee shops and restaurants. The room was clean, and has all the extra little perks you can think of (toiletries, beer/water, local recommendations book, etc.). We got great sleep in Axel's place, and we will definitely return in the future. Highly recommend to other couples or single travelers as you'll feel safe! Thanks again, Axel.