Townhome vacation rentals in South Side

A spacious living area showcases a comfortable L-shaped leather sofa adorned with decorative pillows. A glass coffee table is positioned on an elegant area rug, while framed art pieces decorate the walls. A floor lamp provides soft lighting next to a small side table with a decorative plant.

4.98 out of 5 average rating, 327 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

Located in the heart of Lincoln Park's Armitage/Halsted shopping district, one of Chicago's most desirable and walkable neighborhoods, steps from boutiques, cafés and public transit are all within a short walk. This is an urban, pedestrian friendly neighborhood where many visitors choose to explore on foot. Complimentary daily parking permits included. Please note that the apartment does not have an in-unit washer/dryer. For longer stays, laundry credit is provided for wash and fold service.

4.93 out of 5 average rating, 145 reviews

Chic Lincoln Park Townhome | Rooftop + Glam Bar

Welcome to The Lucky Penny! ⭐️ Lincoln Park Luxury | Rooftop + Glam Station | Sleeps 10 ⭐️ Stay in the heart of Lincoln Park, one of Chicago’s most vibrant neighborhoods, where tree-lined streets meet world-class dining, shopping, nightlife, and the lakefront. This beautifully curated 3-story townhome blends luxury, comfort & style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & lakefront

An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.

4.99 out of 5 average rating, 282 reviews

HUGE 4BR Townhouse FultonMarket/WestLoop!

Stay in a spacious 4-story townhouse in Chicago's vibrant West Loop/Fulton Market, just steps from Restaurant Row, award-winning restaurants, nightlife, coffee shops, parks, and grocery stores. Enjoy the excitement of the neighborhood while staying on a quiet, treelined street for a peaceful night's sleep.Features include a private rooftop terrace with skyline views, an attached garage (1 regular vehicle fits), and easy access to public transit for O'Hare, downtown, Navy Pier, Mag Mile and more.

A spacious living area features a light blue couch with patterned pillows, paired with a cream armchair. Light wood floors extend throughout, creating a warm ambiance. A dining area is visible in the background, highlighted by a chandelier and a decorative wall with exposed brick.

4.86 out of 5 average rating, 301 reviews

Live Logan Square The Globally Loved Neighborhood

Discover your serene Logan Square oasis on a quiet cul-de-sac, just steps from Milwaukee Ave’s top restaurants, bars, Maplewood Brewery, Stan Mansion, Rosa’s Blues Lounge & The Whale. Explore the 606 Trail, hop the Blue Line to airports & downtown, Fullerton bus to Lincoln Park Zoo, and Lakefront or stroll to Bucktown, Wicker Park & the public library a block away. Enjoy self-check-in, free street parking, a fully equipped kitchen, 4 BR, 2 BA, washer/dryer & yard. (No parties per Chicago regs.)

A bright living room features two light-colored sofas arranged around a coffee table. A large artwork adorns the wall above a decorative fireplace, complemented by elegant sconces. Natural light streams through two large windows with black shutters, enhancing the room's open ambiance.

4.99 out of 5 average rating, 161 reviews

Upscale Home in Lincoln Park Minutes from Downtown

Minutes outside downtown Chicago, built in 1890, this gorgeous fully-remodeled modern Victorian-era row house is located in the heart of Chicago’s historic and vibrant Lincoln Park. One of Chicago’s most affluent neighborhoods! > Walkability score of 98/100 > 4 min walk to the train station, steps to bus stops, short Uber ride to all top Chicago attractions > Across DePaul > Amazing parks & bike trails, free zoo, performing arts, shops, nightlife, spas & some of Chicago’s finest restaurants

The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.

4.82 out of 5 average rating, 247 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

A spacious living area features a comfortable gray sectional sofa adorned with light-colored throw pillows, set against a backdrop of large windows draped with sheer curtains. A round dining table with gray chairs and a sleek kitchen area are visible, creating an inviting open space.

4.97 out of 5 average rating, 116 reviews

Cozy & Bright Townhome near O’hare -Self Check In-

Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

5 out of 5 average rating, 122 reviews

An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.

Townhouse in Evanston

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

A contemporary living space features a comfortable gray sofa adorned with pillows and a cozy throw. A dining table is set for four, with white plates and light floral arrangements. Large windows with sheer curtains allow natural light to brighten the room.

4.98 out of 5 average rating, 149 reviews

𓃥Wicker Cozy Corner w/Parking on site

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.

4.95 out of 5 average rating, 129 reviews

A sleek wall-mounted television is set above a modern electric fireplace, framed by a stylish metallic trim. The stone feature wall provides a textured backdrop, while warm wood flooring complements the contemporary design.

Townhouse in Des Plaines

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport

Free! coffee station with 12 types of Keurig pods such as Dunkin/Starbucks/McDonalds/Green tea/Decaf etc. Make your favorite coffee on our commercial brewer. Newly remodeled, luxurious, 3 bedrooms, 1.5 bathrooms duplex house located 10 minutes from O’Hare International Airport. 10-15 minutes from Allstate Arena, Rosemont Convention Center, Fashion Outlets of Chicago and Rivers Casino. Downtown Chicago is ~25 minutes away with an easy access to I-94 and I-294 Expressways

A modern dining area features a dark wood table surrounded by six black chairs. A vase of colorful flowers sits at the center. A large clock hangs on the wall, and natural light filters through sheer curtains leading to a small balcony.

4.88 out of 5 average rating, 112 reviews

Spacious 4BR, central ChinaTown by McCormick/DWNT

Unique 2 story duplex situated in the heart of Chinatown. It’s beautiful, modern and newly furnished 4bedrm/3baths for business conventions and vacation travel. One FREE private parking and plenty of street parking. This home has 8 beds, 2 sofa beds can accommodate 16 or more guests. Walking distance to Ping Tom Park for Water Taxi, Public Transportation, Starbucks, McCormick Place Convention Center, Wintrust Arena. Minutes to Downtown and popular attractions.

The exterior of the United Center is illuminated at night, showcasing vibrant digital displays featuring team logos. Large glass doors welcome visitors. The venue, known for hosting concerts and sports events, is recognized by its prominent signage.