Pet-friendly holiday rentals in Old Town

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Old Town

  • Total holiday rentals

    Explore 30 holiday rentals in Old Town

  • Nightly prices starting at

    Old Town holiday rentals start at $187 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Old Town holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Town rentals

  • 4.8 Average rating

    Old Town stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Old Town

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

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Guest favourite
Apartment in Old Town Triangle
4.77 out of 5 average rating, 268 reviews

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.

Guest favourite
An open-concept loft showcases a cozy seating area with a grey couch adorned with yellow and patterned throw pillows. The kitchen, visible in the background, features modern appliances and a bar with two stools. A lofted sleeping area is bordered by a wooden railing.
Loft in Chicago
4.96 out of 5 average rating, 241 reviews

Lincoln Park Light-Filled Loft

Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows & the conveniences of your own two level suite. A converted store-front, this space is perfect for a couples weekend in Chicago, that friends get-away, or a place to call home for your small family vacation. Walk the neighborhoods & parks, and wonder why you’re not staying longer. We call this our little gem of a find, and are excited to share it with you. We love it, so will you!

Top Guest favourite
A cozy sleeping area features two sets of full over full bunk beds against a light wall, each topped with white bedding. A round mirror hangs above a simple desk, and two accent chairs provide additional seating around a circular wooden coffee table.
Home in Old Town
4.95 out of 5 average rating, 144 reviews

Luxury SOHO Styled Two-Level Townhouse - Old Town

NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.

Top 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
4.97 out of 5 average rating, 169 reviews

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.

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
4.96 out of 5 average rating, 248 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, 153 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 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.
Condo in Chicago
4.97 out of 5 average rating, 143 reviews

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.

Superhost
A modern bedroom features a spacious bed adorned with crisp white linens and decorative pillows. Two stylish bedside lamps provide soft lighting, and a framed art piece adds a contemporary touch to the wall. Large windows offer abundant natural light and views of the surrounding area.
Apartment in Near North Side
4.86 out of 5 average rating, 109 reviews

Kasa | Explore Millennium Park | River North

Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand new high-rise, our modern apartments include state-of-the-art amenities as well as chic details like gourmet kitchens and high ceilings. You’re less than a mile from the Museum of Contemporary Art, The Wrigley Building, and more. Our tech-enabled apartments offer self check-in at 4 pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Top Guest favourite
The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.
Condo in Lincoln Park
4.99 out of 5 average rating, 331 reviews

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 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 fireplace is not operational.

Superhost
An open-concept living area features a spacious dining table surrounded by black chairs. A modern kitchen showcases stainless steel appliances and upper cabinets. Natural light fills the room through multiple windows, while a comfortable sofa is positioned nearby, welcoming relaxation in the thoughtfully designed space.
Condo in Lincoln Park
4.77 out of 5 average rating, 260 reviews

Modern Luxury In Old Town - Sleeps 4

Stay in one of the best neighborhoods in Chicago - Old Town! Recently renovated spacious top floor condo with all modern amenities, in a classic 19th century Chicago home in one of the best parts of the city with access to dining, bars, entertainment and more. Ideal for traveling families and friends, and plenty of Chicago culture nearby, from nearly every era. A neighborhood bar with Frank Sinatra's favorite ribs! Michelin-starred restaurants!

Guest favourite
Condo in Old Town Triangle
4.76 out of 5 average rating, 333 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

Superhost
A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.
Condo in Old Town Triangle
4.87 out of 5 average rating, 187 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Popular amenities for Old Town pet-friendly home rentals

When is the best time to visit Old Town?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$238 NZD$318 NZD$356 NZD$369 NZD$446 NZD$410 NZD$543 NZD$463 NZD$427 NZD$376 NZD$240 NZD$240 NZD
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