
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

Casa PLZN| Location | Entire Home | Garage Parking

BoHo House - A Chic, 1903 Chicago Workers Cottage

Victorian House in Heart of Rogers Park

Quiet cul-de-sac with huge fenced in backyard

Beautiful Chicago Greystone

Adorable house Madison Street w/ 2 car garage!
Pet-friendly home rentals with a pool

Luxury Designer Penthouse NW | Pool | Gold Coast

Sentral Premium 2BR Apt South Loop Chicago

Luxury Penthouse: 3BR, Prime Location

Long term rental-Delightful one bdrm pool house

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

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Level ◆ New Luxe Two Bedroom Corner Suite

Level ◆ Studio Apartment
Private, pet-friendly home rentals

Cabin 106 at 747 Lofts

Full Luxury Home in Wrigleyville

Bright & Spacious| Free Parking |Trendy Bridgeport

Culinary DREAM - Pizza Oven/BBQ/Smoker

The Elstonian Stylish Bucktown Home

Darling Flat Walk to OP

Vital Urban: Spa Inspired Retreat

Apartment on the Lake
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Apartment rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with beach access Downtown Chicago
- Townhouse rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Waterfront rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna 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
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Food and drink Downtown Chicago
- Sightseeing Downtown Chicago
- Nature and outdoors Downtown Chicago
- Sports activities Downtown Chicago
- Tours Downtown Chicago
- Things to do Cook County
- Tours Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Sports activities Cook County
- Food and drink Cook County
- Things to do Illinois
- Sports activities Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Tours Illinois
- Nature and outdoors Illinois
- Things to do United States
- Entertainment United States
- Wellness United States
- Art and culture United States
- Sports activities United States
- Food and drink United States
- Nature and outdoors United States
- Tours United States
- Sightseeing United States