Pet-friendly holiday rentals in South Loop

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in South Loop

Total holiday rentals
Explore 120 holiday rentals in South Loop
Nightly prices starting at
South Loop holiday rentals start at $76 SGD per night before taxes and fees
Verified guest reviews
Over 6,700 verified reviews to help you choose
Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities
Holiday rentals with a pool
60 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
120 of South Loop holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across South Loop rentals
4.8 Average rating
South Loop stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in South Loop

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

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Guest favourite

A spacious kitchen features modern cabinetry and stainless steel appliances. An island with bar seating for eight is complemented by sleek blue chairs. Natural light fills the area from large windows, illuminating the open layout that transitions into a cozy dining space.

Home in South Loop

Large Home | Free Parking | Near Downtown

WalkabilityOutdoor spacesCleanliness

4.89 out of 5 average rating, 126 reviews

Guest favourite

The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.

Home in Lincoln Park

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

WalkabilityPetsAccess

4.95 out of 5 average rating, 195 reviews

Guest favourite

A well-lit living space features large curved windows that offer views of the city. A comfortable dark gray sofa is arranged with decorative pillows. An orange chair adds a pop of color, while a wooden coffee table sits atop a blue area rug. A wall-mounted TV is visible.

Serviced apartment in The Loop

MICH AVE Downtown 2bd, Grant Park Museums #25

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: Guests love staying with us because: ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ Beautiful views of Chicago ✅ Shared Rooftop Deck w Grills ✅ Central Location ✅ FAST WIFI ✅ Comfy KING beds ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Outdoor spacesWalkabilityComfort

4.88 out of 5 average rating, 99 reviews

Top guest favourite

A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

Apartment in Wicker Park

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.

PetsWalkabilityHospitality

4.98 out of 5 average rating, 167 reviews

Top guest favourite

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

Flat in Downtown Chicago

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 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.***

PetsWalkabilityBiking

4.98 out of 5 average rating, 164 reviews

Guest favourite

Flat in Downtown Chicago

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

WalkabilityOutdoor spacesGrill

4.9 out of 5 average rating, 125 reviews

Guest favourite

Apartment in West Side

Charming Condo near U.C./Loop/McCormick Place

Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.

WalkabilityPetsCondition

4.81 out of 5 average rating, 219 reviews

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Flat in Downtown Chicago

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.

PetsWalkabilityValue

4.81 out of 5 average rating, 1040 reviews

Guest favourite

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

Flat in Bridgeport

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Outdoor spacesWalkabilityLocation

4.93 out of 5 average rating, 244 reviews

Top guest favourite

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

Flat in Hyde Park

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.

WalkabilityPetsLayout

4.94 out of 5 average rating, 582 reviews

Guest favourite

Apartment in The Loop

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

WalkabilityOutdoor spacesAccess

4.82 out of 5 average rating, 260 reviews

Guest favourite

A spacious bedroom is featured, highlighted by a large bed with a decorative white coverlet. Two bedside lamps flank the bed, and a round mirror is mounted above the headboard. A soft area rug lies on the floor, and natural light enters through large windows.

Flat in West Side

816 PLZN Penthouse| Rooftop| Garage Parking

Welcome to your stylish retreat in vibrant PILSEN! This modern apartment offers garage parking, a rooftop with stunning views of Willis Tower, and a cozy firepit for relaxing evenings. Explore the neighborhood's murals, visit local bars like Simones, and enjoy Sunday brunch at Duseks. Catch a concert at Thalia Hall or sing your heart out at karaoke bars nearby. Experience the best of art, food, and entertainment in PILSEN – book your stay now!

WalkabilityOutdoor spacesCheckout

4.8 out of 5 average rating, 180 reviews