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Pet-friendly holiday rentals in Skokie

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Skokie

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

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Apartment in Park Ridge

4.79 out of 5 average rating, 321 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

9 – 16 Jan

$1,657 AUD total

Guest favourite

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

5 – 12 Mar

$1,660 AUD total

Guest favourite

Home in Berwyn

4.92 out of 5 average rating, 237 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.

19 – 26 Sept

$1,143 AUD total

Guest favourite

Condo in Chicago

4.93 out of 5 average rating, 186 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

16 – 23 Oct

$1,463 AUD total

Guest favourite

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

15 – 22 Jan

$1,559 AUD total

Guest favourite

Guest suite in Chicago

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!

12 – 19 Sept

$1,630 AUD total

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 176 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.

10 – 17 Mar

$1,633 AUD total

Guest favourite

Apartment in Chicago

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".,

26 Dec – 2 Jan

$1,506 AUD total

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 293 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.

8 – 15 Apr

$1,164 AUD total

Guest favourite

Apartment in Evanston

4.96 out of 5 average rating, 153 reviews

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

27 Nov – 4 Dec

$3,573 AUD total

Guest favourite

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

29 Sept – 6 Oct

$1,366 AUD total

Guest favourite

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

During this time, we are taking extra precautionary measures to ensure our guests safety. Cute and private micro studio in phenomenal downtown Wilmette location. Steps from all local restaurants, shopping, and the Metra station. Walkable to Gillson Beach and the Linden CTA stop. Enter through the front gate to an open & shared yard with private, single access to the unit. Pets OK with additional pet fee (some breed / weight restrictions).

22 – 29 June

$1,610 AUD total

Holiday rentals for every style

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Popular amenities for Skokie pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Guest favourite

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

9 – 16 Dec

$1,724 AUD total

Guest favourite

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

20 – 27 June

$1,816 AUD total

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 126 reviews

Chicago Riverhouse summer on our patio!

7 – 14 Sept

$4,288 AUD total

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

16 – 23 Nov

$1,477 AUD total

Home in Highland Park

4.91 out of 5 average rating, 109 reviews

Rejuvenate and Relax in the North Shore

23 – 30 Oct

$6,229 AUD total

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 100 reviews

Luxury House 6BED/2.5BATH/4PARKING close to lake

19 – 26 Aug

$6,940 AUD total

Home in Des Plaines

4.83 out of 5 average rating, 167 reviews

Exotic House - Few minutes from O'Hare and Chicago

19 – 26 Jan

$2,763 AUD total

Guest favourite

Home in Skokie

4.96 out of 5 average rating, 28 reviews

Luxe Limewash Getaway w/Sun Deck

13 – 20 Dec

$2,630 AUD total

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

25 Oct – 1 Nov

$13,392 AUD total

Apartment in Chicago

4.78 out of 5 average rating, 156 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

5 – 12 Feb

$4,047 AUD total

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

Cozy studio near Michigan lake

9 – 16 July

$1,861 AUD total

Guest favourite

Apartment in Rosemont

5.0 out of 5 average rating, 14 reviews

Relaxing Standard Room l Free Airport Shuttle

24 – 31 Aug

$2,607 AUD total

Guest favourite

Campsite in Midlothian

4.99 out of 5 average rating, 76 reviews

Waverly Woods Outpost: Private Glampsite w Theater

23 – 30 Oct

$2,162 AUD total

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 5 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym

21 – 28 May

$8,092 AUD total

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Luxury Designer Penthouse South |Pool| Gold Coast

29 Jan – 5 Feb

$8,305 AUD total

Apartment in Chicago

5.0 out of 5 average rating, 10 reviews

Skyline Oasis: City & Lake Views

12 – 19 Oct

$5,609 AUD total

Private, pet-friendly home rentals

Apartment in Chicago

4.86 out of 5 average rating, 101 reviews

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

13 – 20 Apr

$1,206 AUD total

Guest favourite

Apartment in Wilmette

4.89 out of 5 average rating, 235 reviews

Spacious Garden Apartment with Sauna and Fireplace

13 – 20 June

$3,002 AUD total

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 396 reviews

Andersonville Living

12 – 19 Oct

$2,135 AUD total

Guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 119 reviews

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

21 – 28 Apr

$1,571 AUD total

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 339 reviews

Sunny Logan Square Artists' home

7 – 14 Mar

$1,598 AUD total

Guest favourite

Apartment in Forest Park

4.85 out of 5 average rating, 110 reviews

Home away from home downstairs

24 – 31 Aug

$1,430 AUD total

Guest favourite

Apartment in Oak Park

4.91 out of 5 average rating, 103 reviews

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

1 – 8 Oct

$1,908 AUD total

Guest favourite

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

21 – 28 Sept

$1,793 AUD total

Quick stats about holiday rentals that are pet-friendly in Skokie

Total rentals
40 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
40 properties include access to Wi-Fi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.5K reviews

Destinations to explore