Pet-friendly vacation rentals in Chicago Loop

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Chicago Loop

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

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A modern living area features a dark gray sofa, complemented by decorative pillows and a coffee table. Large windows provide ample natural light and city views, while plants add a touch of greenery. The space is designed with clean lines and a neutral palette.
Apartment in Chicago Loop
4.76 out of 5 average rating, 208 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, tall ceilings, and oversized windows, this spacious unit is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal

Top guest favourite
A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.
Condo in Lake View
4.98 out of 5 average rating, 110 reviews

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Guest favourite
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 North Park
4.96 out of 5 average rating, 189 reviews

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Top guest favourite
The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.
Apartment in Magnificent Mile
4.98 out of 5 average rating, 180 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Top guest favourite
A cozy seating area features a round table surrounded by two chairs. A potted plant is positioned nearby, contributing to the fresh atmosphere. A glass coffee table rests on a patterned rug, while a comfortable gray sofa with assorted cushions is present against the wall.
Apartment in Wicker Park
4.98 out of 5 average rating, 303 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Top guest favourite
A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.
Apartment in Roscoe Village
4.95 out of 5 average rating, 212 reviews

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!

Top guest favourite
A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.
Apartment in Lincoln Park
4.99 out of 5 average rating, 138 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Top guest favourite
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.
Apartment in Near North Side
4.83 out of 5 average rating, 842 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.

Guest favourite
A modern living area features a dark sofa adorned with colorful throw pillows. A wooden coffee table rests in front, and light streams in through large windows that offer views of the surrounding city. A dining table with chairs is visible in the background.
Condo in Grant Park
4.89 out of 5 average rating, 146 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Guest favourite
An open living space is featured, showcasing a pool table at the center. A staircase spirals to the upper level, while a dining area and modern kitchen are visible in the background. Natural light fills the area, enhancing the spacious atmosphere.
Loft in West Town
4.86 out of 5 average rating, 112 reviews

Modern, Stylish West Town Loft with Pool Table

Spacious, open, and modern, my two bedroom loft is the perfect spot to welcome you to the Windy City. All the comforts of home are provided to you to ensure a comfortable stay. Downtown is just 10 minutes away, and there's plenty to do within walking distance as well! You'll love exploring the city from this centrally located base, coming back in the evening to shoot some pool and unwind, and resting up to do it all again the next day. Don't miss out on this gem, book today!

Guest favourite
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 River West
4.87 out of 5 average rating, 156 reviews

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

Guest favourite
An open living area features a light-colored sofa facing a modern fireplace and a flat-screen television. A dining table with chairs is positioned nearby, while a staircase leads to the upper levels. Balanced lighting highlights the neutral tones and spacious layout.
Home in Lincoln Park
4.82 out of 5 average rating, 256 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!

Popular amenities for Chicago Loop pet-friendly home rentals

When is the best time to visit Chicago Loop?

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Avg. price$195 CAD$221 CAD$248 CAD$306 CAD$363 CAD$419 CAD$357 CAD$350 CAD$339 CAD$350 CAD$290 CAD$234 CAD
Avg. temp-3 °C-1 °C4 °C10 °C16 °C22 °C25 °C24 °C20 °C13 °C6 °C0 °C

Quick stats about vacation rentals that are pet-friendly in Chicago Loop

  • Total vacation rentals

    Explore 600 vacation rentals in Chicago Loop

  • Nightly prices starting at

    Chicago Loop vacation rentals start at $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 9,950 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    360 properties feature pools

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wifi availability

    600 of Chicago Loop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chicago Loop rentals

  • 4.7 Average rating

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

  • Nearby attractions

    Chicago Loop’s top spots, include Millennium Park, Shedd Aquarium, and Willis Tower

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