
Pet-friendly vacation rentals in Woodlawn
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Woodlawn
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

PRIVATE 2-bedroom 1.5 bath w/ living room
Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

Rare 1BR Lincoln Park Apt, close to everything!
Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Wicker Park Walk-Up Condo
Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Modern Getaway w/ Hot Tub, Lrg Yard, Parking
1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Beverly Cottage Loft
Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Susie's Space. 2BR easy parking & pet friendly
Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Penthouse Near Wrigley Field
This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Stylish 2BR stunner w/ unbeatable location
Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.

Designer Loft in Fulton Market with Parking
Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.
Popular amenities for Woodlawn pet-friendly home rentals
Pet-friendly house rentals

Private 3rd Floor Apartment

Urban Chic 3beds w/2bath + free parking & W/D

BoHo House - A Chic, 1903 Chicago Workers Cottage

Warm and comfortable inviting Suburban home !

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

Quiet cul-de-sac with huge fenced in backyard

Beautiful Chicago Greystone

Cozy House with Gazebo
Pet-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

Munster hide away

Level Junior Two Bedroom Suite | Fulton Market

Sentral Premium 2BR Apt South Loop Chicago

Forest Park Oasis - Dog Friendly - Parks - the "L"

Stunning 3BR Penthouse in the Loop | Roof Deck

Two 2BR Apts for Business & Leisure Groups

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Private, pet-friendly home rentals

Modern Family Townhouse

Historic mini mansion!

Roomy 1BR Apt w/ In-Unit Laundry

Live Stylish in Hyde – 2BR Haven

Bright & Cozy Studio in the Heart of Hyde Park

Kasa | Spectacular City Views | Chicago

Your second home in Chicago

420-Friendly 2BR Retreat • Private Yard Near DT
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ345 | ﺩ.ﺇ342 | ﺩ.ﺇ378 | ﺩ.ﺇ371 | ﺩ.ﺇ411 | ﺩ.ﺇ430 | ﺩ.ﺇ466 | ﺩ.ﺇ426 | ﺩ.ﺇ382 | ﺩ.ﺇ411 | ﺩ.ﺇ364 | ﺩ.ﺇ367 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about vacation rentals that are pet-friendly in Woodlawn

Total vacation rentals
Explore 50 vacation rentals in Woodlawn

Nightly prices starting at
Woodlawn vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,610 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
40 of Woodlawn vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodlawn rentals

4.5 Average rating
Woodlawn stays receive an average rating of 4.5 out of 5 from guests
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- Pet-friendly rentals Chicago
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- Pet-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- University of Chicago
- Washington Park Zoo




