Pet-friendly vacation rentals in Old Town

4.99 out of 5 average rating, 185 reviews

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.

Condo in Lincoln Park

❤︎ 1,800ft² Parking ⎜ Workspace ⎜ W/D ⎜Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian 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

Apartment in Old Town Triangle

4.77 out of 5 average rating, 258 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.

Apartment in Lincoln Park

A spacious living area features a gray sofa adorned with yellow cushions, accompanied by two beige armchairs. An archway leads to a contemporary kitchen, while soft lighting and a neutral color palette create a calm atmosphere.

4.84 out of 5 average rating, 331 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history to its modern comforts. Featuring warm timber floors that connect two cozy bedrooms with queen beds to a contemporary kitchen. Each room has a TV, and the kitchen is fully stocked for your convenience. With two full bathrooms and barrier-free one-floor access, this space combines old-world charm with modern living in the vibrant heart of Lincoln Park, close to the Lakefront.

4.97 out of 5 average rating, 162 reviews

A two-story white house is featured, displaying large windows that allow natural light to brighten the façade. The entrance is marked by a covered porch with steps leading up, while planters are placed on either side of the door against a tree-dappled background.

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.

4.98 out of 5 average rating, 316 reviews

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

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.

Apartment in Lincoln Park

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.

4.99 out of 5 average rating, 147 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.

Apartment in Noble Square

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, 582 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

4.89 out of 5 average rating, 164 reviews

A cozy living area is presented with natural light filtering through the wooden blinds. A light-toned sofa with patterned cushions faces a wooden coffee table, accompanied by a flat-screen TV. Colorful area rugs and a potted plant add warmth to the space.

Apartment in Chicago

Sounds Of The City

Fun and lively location! Cozy one-bedroom "stumbling distance" from McGee's Tavern and Grille, as in right upstairs. It’s pretty peaceful during the day except some train noise. The popular bar below is temp closed so no noise issue at moment. Lincoln Park is an upscale, safe & convenient area. Walking distance to cafes, dining, pubs, parks, transportation, Lyft bikes, yoga, fitness, Amazon, etc. Weekends draw the biggest crowds and noise. Free street parking.Easy Uber/Lyft

4.82 out of 5 average rating, 129 reviews

A comfortable living area features a light gray sectional sofa and a matching armchair, arranged around a carpet with vibrant patterns. A small wooden side table holds an assortment of snacks. Kitchen space is visible in the background, providing an open layout.

Apartment in Chicago

Cityscape - Heart of Lincoln Park/DePaul

“L”evate your Chicago experience in this VERY lively location. Cozy 1-bedroom right next to the “L” tracks so it’s LOUD AF, LOL!! Best for guests who aren’t sensitive and can tolerate train noise. Lincoln Park is an upscale, safe & convenient area. Walking distance to great dining options, cafes, pubs, parks, trains/buses, ride-share, Target, Lyft bike, yoga, gym. Free street parking, parking stickers provided which are needed for relatively easy overnight parking.

4.93 out of 5 average rating, 244 reviews

A bright living area features large bay windows with natural light filtering through. A white sofa is complemented by decorative pillows and a coffee table adorned with flowers. A mirror adorns the wall, enhancing the sense of space and light.

Apartment in Lake View

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Condo in Old Town Triangle

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.

4.88 out of 5 average rating, 181 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!

4.97 out of 5 average rating, 459 reviews

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

Condo in Lincoln Square

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Popular amenities for Old Town pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 119 reviews

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

Home in North Side

Flat in Lincoln Park 2-Flat Central to Everything

4.91 out of 5 average rating, 402 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 Lake View

Private 3rd Floor Apartment

4.96 out of 5 average rating, 197 reviews

An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.

Home in North Park

The Chicago River House – GIANT wall projector!

4.84 out of 5 average rating, 122 reviews

An open living and dining area is shown, featuring a flat-screen TV mounted on a light wood unit. Comfortable seating includes a gray sofa, teal chairs, and a pink armchair. A wooden dining table is set for six. Decorative elements include wall art and a wall clock.

Home in Logan Square

California Cottage/4br prime location Logan Square

4.98 out of 5 average rating, 165 reviews

A stylish living room features a glass coffee table atop a textured rug, surrounded by two orange, velvet armchairs and a plush, patterned sofa. A decorative fireplace is framed by elegant vases, with a mirror reflecting natural light from the windows.

Home in Wicker Park

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

4.92 out of 5 average rating, 181 reviews

A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.

Home in Avondale

BoHo House - A Chic, 1903 Chicago Workers Cottage

4.98 out of 5 average rating, 118 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 Chicago

Victorian House in Heart of Rogers Park

4.97 out of 5 average rating, 139 reviews

The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.

Home in Portage Park

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Pet-friendly home rentals with a pool

4.77 out of 5 average rating, 123 reviews

Apartment in River North

Level ◆ Brand New Luxe One Bedroom

Apartment in Magnificent Mile

4.82 out of 5 average rating, 65 reviews

Luxury Designer Penthouse 3801 | Pool | Gold Coast

5 out of 5 average rating, 18 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"

Apartment in Printer's Row

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.

4.92 out of 5 average rating, 101 reviews

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

4.75 out of 5 average rating, 281 reviews

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

Apartment in Fulton Market

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.

4.62 out of 5 average rating, 29 reviews

Level One Bedroom Suite | Fulton Market

4.67 out of 5 average rating, 3 reviews

The living area showcases large floor-to-ceiling windows that invite ample natural light, revealing city views. A modern sofa is positioned on a textured area rug, accompanied by a minimalist coffee table. The kitchen features sleek cabinetry and stainless steel appliances, visible in the background.

Apartment in West Loop

Two 2BR Apts for Business & Leisure Groups

Apartment in Logan Square

A cozy living area is presented, featuring a comfortable sofa and a stylish blue chair. A wooden coffee table sits in the center, complemented by a textured rug. Large windows allow natural light, while art pieces adorn the walls, adding visual interest to the space.

4.8 out of 5 average rating, 76 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

Private, pet-friendly home rentals

Apartment in Logan Square

A warm living area features a black leather sofa adorned with colorful throw pillows. A glass coffee table rests on a patterned rug, while two accent chairs provide additional seating. Natural light streams in through a window, complemented by decorative plants and wall art.

4.95 out of 5 average rating, 318 reviews

Cozy and Spacious! Logan Square Apartment

Apartment in Logan Square

The living area features a vibrant blue sofa complemented by a colorful hammock, surrounded by greenery. A wooden dining table with four chairs sits prominently, while artistic decor is displayed on the walls and a large mirror reflects natural light from multiple windows.

4.9 out of 5 average rating, 439 reviews

Sunny Logan Square Artists' home

4.98 out of 5 average rating, 226 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Condo in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

4.96 out of 5 average rating, 164 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.

Apartment in Wicker Park

Stylish 2BR stunner w/ unbeatable location

4.99 out of 5 average rating, 136 reviews

A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.

Condo in Lake View

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Guesthouse in Logan Square

The living area features a wall-mounted TV opposite a light-colored loveseat and a blue armchair. A small round coffee table is situated on a textured gray rug. Natural light enters through the two windows, with modern framed art and a floor lamp adding character.

4.98 out of 5 average rating, 361 reviews

Private coach house near transit shops & nightlife

4.95 out of 5 average rating, 154 reviews

The living area features exposed brick walls and wooden beams, complemented by a gray sectional sofa and a dark blue armchair. A flat-screen television is mounted on the wall. A coffee table sits atop a patterned rug, and a workspace is located in the corner with a desk and lamp.

Apartment in Bucktown

Garden Unit Getaway-Bucktown