
Pet-friendly holiday rentals in Downtown Chicago
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Downtown Chicago
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago pet-friendly home rentals
Pet-friendly house rentals

Historic Old Town, Fabulous 4 Bedroom Home

Private 3rd Floor Apartment

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

BoHo House - A Chic, 1903 Chicago Workers Cottage

Victorian House in Heart of Rogers Park

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Quiet cul-de-sac with huge fenced in backyard

Beautiful Chicago Greystone
Pet-friendly home rentals with a pool

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Sentral Premium 2BR Apt South Loop Chicago

Long term rental-Delightful one bdrm pool house

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

Level One Bedroom Suite | Fulton Market

Level ◆ Studio Apartment

Luxury Designer Penthouse West |Pool| Gold Coast

Modern 2BR South Loop Apt, McCormick & Wintrust
Private, pet-friendly home rentals

Chicago Vintage & Chic Living

Sun-Soaked West Loop Penthouse/Private Rooftop/3BA

Bright & Spacious| Free Parking |Trendy Bridgeport

Kasa | Studio, Walk to Grant Park | South Loop

cozy grand studio 2nd floor/near lake/public tran.

University of Chicago Condo-Upgraded and Spacious

Lincoln Park Light-Filled Loft

Bright & Modern Lakeview Studio
Destinations to explore
- Chicago Holiday rentals
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- Windsor Holiday rentals
- House rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a patio Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Pet-friendly rentals Cook County
- Pet-friendly rentals Illinois
- Pet-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Illinois Beach State Park
- Lincoln Park Zoo
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Sightseeing Downtown Chicago
- Food and drink Downtown Chicago
- Sports activities Downtown Chicago
- Nature and outdoors Downtown Chicago
- Tours Downtown Chicago
- Art and culture Downtown Chicago
- Things to do Cook County
- Sightseeing Cook County
- Sports activities Cook County
- Tours Cook County
- Food and drink Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Illinois
- Art and culture Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Food and drink Illinois
- Tours Illinois
- Nature and outdoors Illinois
- Things to do United States
- Tours United States
- Food and drink United States
- Nature and outdoors United States
- Sightseeing United States
- Art and culture United States
- Sports activities United States
- Entertainment United States
- Wellness United States