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

Flat in Lincoln Park 2-Flat Central to Everything
Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Private coach house near transit shops & nightlife
This newly renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Modern vintage chic steps from Wrigley: park free
Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. Charming vintage DNA meets modern amenities. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom. Chicago Shared Housing Registration: R22000093584

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.

Victorian House in Heart of Rogers Park
Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Best in Chicago, private, amazing garden space
We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

The Huron Haven
A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Elegant Suite in Gold Coast
Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of July 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Stunning Corner 2BR in the Loop | City & Lake View
Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city and lake views in multiple directions. This stylish light-filled two bedroom, two bathroom space is perfect for groups looking for a luxurious getaway in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!
Popular amenities for Chicago pet-friendly home rentals
Pet-friendly house rentals

Historic Old Town, Fabulous 4 Bedroom Home

Step Outside to Shops and Restaurants

Private 3rd Floor Apartment

The Chicago River House – GIANT wall projector!

BoHo House | Chic, 1903 Chicago Workers Cottage

ALOHA 2.0 | Patio, 2 Parking, Sleeps 23

Beautiful Chicago Greystone

Spacious Luxury Townhouse - Old Town
Pet-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

Munster hide away

Luxury Designer Penthouse 3803 | Pool | Gold Coast

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

Level One Bedroom Suite | Fulton Market

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

King Queen Bunk Bed Cozy Munster MiniGolfHouse

Paradise with Pool & Games
Private, pet-friendly home rentals

Wicker Park Walk-Up Condo

City Urban Loft in the Heart of Wicker Park!

Full Luxury Home in Wrigleyville

Summer Break Incoming! Live Like an A-ville Local!

Spacious Studio in Little Italy, Near West Loop

Bright & Spacious Boho Oasis: A Warm Retreat

Executive Apartment on Lake Michigan with parking

Two Bedroom w Porch in Wicker Park
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 SGD | $169 SGD | $192 SGD | $204 SGD | $238 SGD | $240 SGD | $233 SGD | $245 SGD | $221 SGD | $215 SGD | $184 SGD | $179 SGD |
| 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 holiday rentals that are pet-friendly in Chicago

Total holiday rentals
Explore 3,620 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 165,090 verified reviews to help you choose

Family-friendly holiday rentals
2,000 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
700 properties feature pools

Rentals with dedicated workspaces
2,400 properties have a dedicated workspace

Wifi availability
3,550 of Chicago holiday rentals include wifi access

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

4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Destinations to explore
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- Pet-friendly rentals Cook County
- Pet-friendly rentals Illinois
- Pet-friendly rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Museum of Science and Industry
- Oak Street Beach
- Illinois Beach State Park
- Indiana Dunes State Park
- Willis Tower
- Things to do Chicago
- Sightseeing Chicago
- Tours Chicago
- Nature and outdoors Chicago
- Sports activities Chicago
- Art and culture Chicago
- Food and drink Chicago
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