Pet-friendly holiday rentals in The Loop

4.89 out of 5 average rating, 129 reviews

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

Outdoor spacesWalkabilityView

4.78 out of 5 average rating, 291 reviews

Flat in Lincoln Park

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.

PetsOutdoor spacesQuiet

4.95 out of 5 average rating, 198 reviews

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.

WalkabilityPetsKitchen

4.98 out of 5 average rating, 171 reviews

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.

PetsOutdoor spacesQuiet

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.

4.98 out of 5 average rating, 166 reviews

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.***

PetsWalkabilityValue

4.93 out of 5 average rating, 118 reviews

A spacious bedroom is highlighted by a large king bed with a textured green headboard. Natural light floods the room through expansive windows offering views of the city and lake. A colorful area rug enhances the space, while modern artwork is displayed on the walls.

Flat in The Loop

Dtown Penthouse 11+Parking, Gym, Pvt Patio

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: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

Outdoor spacesWalkabilityWifi

An open kitchen and dining area feature a modern design with sleek cabinetry and a large island. A generous dining table, surrounded by black chairs, offers seating for multiple guests. Natural light floods the space through large windows, with minimal decor enhancing the contemporary aesthetic.

4.96 out of 5 average rating, 112 reviews

Luxury Loft Collection 03 - 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!

Outdoor spacesWalkabilityAccuracy

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

4.97 out of 5 average rating, 636 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

WalkabilityPetsKitchen

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.

4.81 out of 5 average rating, 1055 reviews

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.

Outdoor spacesWalkabilityLong stay

Apartment in Lincoln Park

A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Brick Building . You have 3 flight of stairs to climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

WalkabilityPetsParking

4.99 out of 5 average rating, 223 reviews

4.87 out of 5 average rating, 233 reviews

A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.

Guest suite in West Town

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

Outdoor spacesWalkabilityValue

4.95 out of 5 average rating, 119 reviews

A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.

Flat in The Loop

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

PetsWalkabilityAccuracy

Popular amenities for The Loop pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.87 out of 5 average rating, 212 reviews

A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.

Home in Lincoln Park

Historic Old Town, Fabulous 4 Bedroom Home

PetsOutdoor spacesDecor

4.96 out of 5 average rating, 213 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in Chicago

The Chicago River House – GIANT wall projector!

Outdoor spacesWalkabilityTV

4.95 out of 5 average rating, 106 reviews

An outdoor patio area is shown with a glass table and two metal chairs. Potted plants and flowers add greenery along the edges. A brick wall provides a rustic backdrop, while a staircase is visible in the background, leading to the upper level.

Home in Lincoln Park

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

Outdoor spacesWalkabilityLocation

4.92 out of 5 average rating, 151 reviews

An elegant 1890 Greystone building is presented, showcasing a symmetrical façade with decorative stonework. A tiered front staircase leads to a charming entryway, flanked by well-maintained landscaping. Large windows enhance natural light, while a vibrant green shrub adds a touch of color to the exterior.

Home in West Side

Beautiful Chicago Greystone

Outdoor spacesPetsAccess

4.98 out of 5 average rating, 140 reviews

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.

Home in East Rogers Park

Victorian House in Heart of Rogers Park

PetsOutdoor spacesCleanliness

4.88 out of 5 average rating, 112 reviews

A spacious living area showcases a mix of comfortable seating, including a sectional sofa and an armchair. Natural light filters through sheer curtains, illuminating the hardwood floor. A neutral area rug lies beneath a coffee table, complementing the decorative wall features.

Home in Irving Park

3BD/2BA Chicago Avondale/Logan Square House

PetsWalkabilityLong stay

4.91 out of 5 average rating, 427 reviews

A spacious dining area features a large table surrounded by six chairs. Natural light is provided by two windows with sheer curtains. A unique light fixture hangs above, and a vase with flowers is centered on the table, contributing to the room's welcoming ambiance.

Home in Uptown

Private 3rd Floor Apartment

WalkabilityPetsHeating

4.97 out of 5 average rating, 143 reviews

A welcoming living room features a mix of modern and cozy furniture, including a brown leather sofa and a light-colored sectional. Natural light fills the space through large windows, while decorative pillows add touches of color. A coffee table rests on a textured area rug.

Home in West Town

The Full House

Outdoor spacesWalkabilityComfort

Pet-friendly home rentals with a pool

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

4.93 out of 5 average rating, 131 reviews

Cozy Duplex Down in Wicker Park East w/ Parking

WalkabilityPetsShared spaces

4.69 out of 5 average rating, 36 reviews

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

Flat in West Loop

Level One Bedroom Suite | Fulton Market

WalkabilityValueCheck-in

4.74 out of 5 average rating, 93 reviews

Flat in East Rogers Park

Cozy studio near Michigan lake

WalkabilityPetsFamily

4.9 out of 5 average rating, 20 reviews

Townhouse in West Town

360RoofSKYview|ARTy|Garage+HotTub|EVTesla|Sleeps12

Outdoor spacesWalkabilityLocation

4.97 out of 5 average rating, 34 reviews

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

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

PetsWalkabilityComfort

A spacious living area features large windows showcasing city views. A modern sofa with accent pillows faces a flat-screen TV, while stylish teal chairs complement the minimalist design. The open layout connects to a fully equipped kitchen visible in the background.

4.83 out of 5 average rating, 47 reviews

3BR Luxury Suite w/Gym and Balcony

Outdoor spacesWalkabilityDecor

5.0 out of 5 average rating, 20 reviews

Spacious 1-Bedroom + Den in the Heart of Chicago

WalkabilityCleanlinessPool

The living area features two gray sofas arranged around a glass coffee table on a patterned rug. A flat-screen TV is placed on a stand, and a well-equipped kitchenette is visible in the background. Soft lighting is provided by floor lamps and overhead fixtures.

Flat in Logan Square

Play in the Windy City and Rest by ‘The 606’

WalkabilityPetsHospitality

4.61 out of 5 average rating, 142 reviews

Private, pet-friendly home rentals

A spacious living area features large windows allowing abundant natural light. Exposed Chicago brick adds character to the space, while hardwood floors extend throughout. A comfortable sectional sofa, a chic armchair, and a tasteful area rug create a welcoming atmosphere. A television and decorative furnishings are also visible.

4.91 out of 5 average rating, 331 reviews

✨Spacious Centrally Located West Loop Loft✨

WalkabilityPetsComfort

4.82 out of 5 average rating, 260 reviews

Apartment in The Loop

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

Outdoor spacesWalkabilityQuiet

4.96 out of 5 average rating, 123 reviews

Apartment in Wicker Park

Two Bedroom w Porch in Wicker Park

PetsWalkabilityHeating

4.9 out of 5 average rating, 176 reviews

A bright and open living space showcases a contemporary seating area with a green sofa and a plush armchair. Natural light floods through large windows, casting a warm glow over the stylish kitchenette and dining table. A smart TV is mounted on the wall, enhancing the modern vibe.

Flat in Little Italy

Modern 1BR in Little Italy, Near West Loop

PetsWalkabilityCleanliness

4.92 out of 5 average rating, 210 reviews

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

Flat in Wicker Park

Stylish 2BR stunner w/ unbeatable location

PetsOutdoor spacesAccess

An open living area displays a modern kitchen with stainless steel appliances and dark cabinetry. A light-colored sofa is positioned beside a wooden coffee table. A glass dining table accommodates four chairs, while a colorful rug adds warmth to the space.

4.85 out of 5 average rating, 456 reviews

Explore the City from an Elegant, Urban Retreat

PetsWalkabilityBathroom

4.95 out of 5 average rating, 444 reviews

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

Flat in Ravenswood

Bright family-friendly Lincoln Square 2-bed 1-bath

WalkabilityPetsPool