Pet-friendly vacation rentals in Wicker Park, Chicago

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Top-rated pet-friendly home rentals in Wicker Park, Chicago

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

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Guest favorite

Apartment in Chicago

4.86 out of 5 average rating, 134 reviews

Oasis Collection's Mid-Century 3 Bd Wicker Park.

Family friendly. The home is updated and a tried and true crowd please. Authentic Chicago experience in the heart of the Wicker Park Historic District. Short walk to restaurants, shopping and nightlife. 3 bedrooms w/ new luxury beds & plush bedding. Spacious living room set up for relaxing or entertaining. Fully provisioned kitchen & bath. Charm, character & quirks abound, so don't expect new construction. The "L" train runs nearby. Ambient city noise expected. Parking & dog policy in “space”.

Aug 2 – 9

G$117,828 GYD per night

Guest favorite

Condo in West Town

4.88 out of 5 average rating, 235 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Welcome to your private home away from home in Ukrainian Village, a Top 10 neighborhood in the nation! Our super comfy 2 King Serta pillowtop mattress in the garden (lower) level condominium with everything you need during your stay and more. We have been told over & over the photos do not do this place justice. Walk to a wide variety of award winning restaurants, hip shopping/coffee shops, grocery, public transport, bars and more! A quiet neighborhood with quick access to all Chicago offers!

Nov 5 – 12

G$32,661 GYD 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

G$22,399 GYD per night

Guest favorite

Apartment in West Town

4.98 out of 5 average rating, 220 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.

Dec 29 – Jan 5

G$51,211 GYD per night

Guest favorite

Guest suite in Logan Square

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

G$23,458 GYD 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

G$31,963 GYD 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

G$21,840 GYD per night

Guest favorite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

This is a private three bedroom house you will be reserving in the Avondale neighborhood with plenty of available free street parking. The residence sits on the intersection of Elston, Rockwell and Wellington. We are in the middle of it all. You can shoot into downtown quickly or be in Wrigleyville within minutes to watch the Cubs. You’ll love this place because of the neighborhood and privacy. The space has been crafted by a well experienced host. 15 minute drive to downtown.

Mar 6 – 13

G$21,008 GYD 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

G$22,874 GYD per night

Guest favorite

Apartment in Lincoln Square

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

G$27,295 GYD per night

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 330 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!

Sep 24 – Oct 1

G$30,190 GYD per night

Guest favorite

Apartment in Chicago

4.93 out of 5 average rating, 207 reviews

Cozy Private Coach House

This is a cozy 1 bedroom unit in a private coach house. Excellent location in the middle of trendy Logan Square! Please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 28 night minimum in the winter, until the end of February or possibly March. But I recommend putting in at least 30 days to avoid those taxes!

Oct 15 – 22

G$28,785 GYD per night