Pet-friendly vacation rentals in Woodlawn, Chicago

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Top-rated pet-friendly home rentals in Woodlawn, Chicago

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Guest favorite

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.

Dec 8 – 15

€ 99 per night

Superhost

Guest suite in Chicago

4.84 out of 5 average rating, 200 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.

Mar 8 – 15

€ 116 per night

Guest favorite

Apartment in Chicago

4.95 out of 5 average rating, 106 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

Jan 24 – 31

€ 146 per night

Guest favorite

Guest suite in Chicago

4.93 out of 5 average rating, 352 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

Jan 24 – 31

€ 138 per night

Guest favorite

Guest suite in Logan Square

4.97 out of 5 average rating, 225 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 7 – 14

€ 144 per night

Guest favorite

Guest suite in Chicago

4.97 out of 5 average rating, 237 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!

Sep 25 – Oct 2

€ 186 per night

Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 237 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Nov 3 – 10

€ 133 per night

Guest favorite

Guest suite in Bridgeport

4.94 out of 5 average rating, 124 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 – 25

€ 163 per night

Guest favorite

Apartment in Oak Lawn

4.95 out of 5 average rating, 123 reviews

Charming One Bedroom Apartment

Enjoy your stay in Oak Lawn in this modern and rustic, newly remodeled one-bedroom apartment! It is conveniently located right by Christ Hospital, Metra station and Midway Airport. The apartment is comfortable for up to 4 people, has a private bedroom and a pull out sofa in the living room. You will have a full kitchen, work space, entertainment area with TV and a comfy bed for your best night rest. There is Wifi, Netflix, hulu, and YouTube TV.

Jul 11 – 18

€ 148 per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 240 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 2 – 9

€ 120 per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 322 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Dec 10 – 17

€ 161 per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 329 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Oct 17 – 24

€ 179 per night