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Pet-friendly vacation rentals in South Side

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in South Side

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest suite in Chicago

4.84 out of 5 average rating, 201 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Guest suite in an 1890 Worker's Cottage with plenty of character, originally built for laborers in the Chicago Stockyards. This quiet neighborhood is a respite from city buzz, just 20 min from the Loop. Your space has great natural light, 2 comfy beds (1 folds to a couch), private bath, flexible work/dining area, super-fast WiFi, and a kitchen with all the essentials. Private entry via back door. Free parking. Get downtown in 4 stops by train or any of 5 nearby buses. Se habla español.

Oct 23 – 30

R1,735 ZAR per night

Apartment in Chicago

4.91 out of 5 average rating, 169 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Sep 8 – 15

R1,491 ZAR per night

Apartment in Chicago

4.95 out of 5 average rating, 109 reviews

Comfortable, modern apartment 20 Min from Downtown

Welcome to Chicago! Whatever reason brings you to my lovely city, I'm sure my house will suit your every need. There are three units with separate entrees, out of which the first unit is for your own use; second unit is rented occasional. I live in the garden apartment, but will be rarely home. This modern unit has: -2 bedrooms 1 queen & 1 double bed -2 full bathroom -washer and a dryer -fully equipped kitchen - Wi Fi -50'' flat screen TV -central Air/Heat - back yard with porch -free parking

Sep 23 – 30

R2,145 ZAR per night

Guest suite in Wood Dale

4.9 out of 5 average rating, 429 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Oct 31 – Nov 7

R2,119 ZAR per night

Home in Berwyn

4.92 out of 5 average rating, 240 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 12 – 19

R1,741 ZAR per night

Guest suite in Chicago

4.93 out of 5 average rating, 353 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

Oct 19 – 26

R2,008 ZAR per night

Apartment in Chicago

4.98 out of 5 average rating, 219 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Jan 3 – 10

R3,021 ZAR per night

Guest suite in Chicago

4.97 out of 5 average rating, 226 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Sep 29 – Oct 6

R2,082 ZAR per night

Guest suite in Chicago

4.97 out of 5 average rating, 238 reviews

Stylish Studio in Historic Logan Square

Brand new, unique 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 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 fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!

Oct 4 – 11

R2,837 ZAR per night

Guest suite in Chicago

4.94 out of 5 average rating, 125 reviews

Comfortable & Cozy in Bridgeport

Cozy in-law apartment (garden-level) in Chicago's Bridgeport neighborhood. Great for a couple, a single person that is "working from home," or young friends. Unique touches like local art (including a hand-painted shower curtain), equipped kitchen, and a mini library out front in case you forgot your book! In a nice, quiet neighborhood that is close to Chinatown, Pilsen, Sox Park, Midway, and McCormick Place. Chicago Registration Number: R21000062030

Jul 20 – 27

R2,149 ZAR per night

Tiny home in Burr Ridge

4.92 out of 5 average rating, 242 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Mar 7 – 14

R2,074 ZAR per night

Apartment in Forest Park

5.0 out of 5 average rating, 221 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

Sep 8 – 15

R2,211 ZAR per night

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Popular amenities for South Side pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jun 25 – Jul 2

R2,854 ZAR per night

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Jan 8 – 15

R2,328 ZAR per night

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

Nov 30 – Dec 7

R1,794 ZAR per night

Home in Chicago

4.96 out of 5 average rating, 127 reviews

Chicago Riverhouse summer on our patio!

Dec 13 – 20

R5,545 ZAR per night

Home in Worth

4.87 out of 5 average rating, 102 reviews

The Comfy King Ranch/ King Bed/Disney+ /Fast Wi-Fi

Dec 10 – 17

R4,626 ZAR per night

Home in Chicago

4.93 out of 5 average rating, 210 reviews

Luxe 6BR House *Trendy Logan Square *Garage Access

Dec 21 – 28

R15,189 ZAR per night

Home in Chicago

4.82 out of 5 average rating, 140 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Jan 22 – 29

R6,683 ZAR per night

Home in Elgin

4.88 out of 5 average rating, 104 reviews

Charming Elgin Home with a Great Location

Oct 26 – Nov 2

R2,424 ZAR per night

Pet-friendly home rentals with a pool

Apartment in Itasca

4.77 out of 5 average rating, 181 reviews

King Bed at Chicago Northwest + PET Friendly

Jun 3 – 10

R3,030 ZAR per night

Apartment in Chicago

4.87 out of 5 average rating, 110 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Nov 27 – Dec 4

R9,343 ZAR per night

Apartment in Chicago

4.86 out of 5 average rating, 190 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

Jan 24 – 31

R6,448 ZAR per night

Apartment in Chicago

4.9 out of 5 average rating, 30 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Mar 19 – 26

R2,923 ZAR per night

Apartment in Chicago

5.0 out of 5 average rating, 8 reviews

Cozy studio near Michigan lake

Jun 30 – Jul 7

R2,330 ZAR per night

Apartment in Rosemont

4.94 out of 5 average rating, 17 reviews

Relaxing Standard Room l Free Airport Shuttle

Jul 8 – 15

R3,478 ZAR per night

Campsite in Midlothian

4.99 out of 5 average rating, 76 reviews

Waverly Woods Outpost: Private Glampsite w Theater

Aug 4 – 11

R3,777 ZAR per night

Apartment in Chicago

4.88 out of 5 average rating, 8 reviews

Safe Downtown Penthouse Lake Views #1|Gym, Parking

Jun 5 – 12

R9,550 ZAR per night

Private, pet-friendly home rentals

Apartment in Chicago

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Dec 2 – 9

R1,939 ZAR per night

Apartment in Chicago

4.92 out of 5 average rating, 152 reviews

Urban Pilsen Apt. near Downtown

Feb 10 – 17

R2,082 ZAR per night

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Sep 13 – 20

R2,365 ZAR per night

Apartment in Chicago

4.89 out of 5 average rating, 339 reviews

Sunny Logan Square Artists' home

Feb 8 – 15

R2,030 ZAR per night

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Jan 12 – 19

R1,803 ZAR per night

Apartment in Forest Park

4.98 out of 5 average rating, 285 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Sep 21 – 28

R2,799 ZAR per night

Apartment in Chicago

4.86 out of 5 average rating, 101 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Apr 4 – 11

R1,503 ZAR per night

Apartment in Oak Lawn

4.95 out of 5 average rating, 123 reviews

Charming One Bedroom Apartment

Jul 11 – 18

R2,470 ZAR per night

Destinations to explore