Pet-friendly vacation rentals in Downtown Chicago

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Top-rated pet-friendly home rentals in Downtown Chicago

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

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Guest favorite

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

Apr 29 – May 6

ﺩ.ﺇ425 per night

Guest favorite

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 8 – 15

ﺩ.ﺇ342 per night

Guest favorite

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

Jan 21 – 28

ﺩ.ﺇ394 per night

Guest favorite

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 28 – Oct 5

ﺩ.ﺇ412 per night

Guest favorite

Apartment in Chicago

4.99 out of 5 average rating, 104 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

Dec 7 – 14

ﺩ.ﺇ530 per night

Guest favorite

Guest suite in Chicago

4.97 out of 5 average rating, 239 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 5 – 12

ﺩ.ﺇ562 per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 177 reviews

Historic Chicago neighborhood flat

Private one-bedroom apartment plus queen sleeper sofa in historic Ravenswood Manor. This unit is on the ground floor of a three-flat on a beautiful tree-lined street with plenty of free parking. Close to Brown Line - Francisco Stop - and lots of neighborhood parks. Close to Rockwell and Lincoln Square shopping and restaurants and next to Albany Park, one of Chicago’s most diverse neighborhoods. New fixtures, furniture, appliances, free shared laundry, access to backyard upon request.

Mar 1 – 8

ﺩ.ﺇ403 per night

Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 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".,

Oct 15 – 22

ﺩ.ﺇ384 per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Feb 19 – 26

ﺩ.ﺇ357 per night

Guest favorite

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

ﺩ.ﺇ425 per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 339 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail.

Feb 18 – 25

ﺩ.ﺇ402 per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 323 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 18 – 25

ﺩ.ﺇ480 per night