Vacation rentals in Chicago

Apartment in Lincoln Park

A large dining table made of wood is surrounded by minimalist lighting fixtures. Natural light enters through multiple windows, highlighting the room's mix of exposed brick and modern furnishings. A cozy seating area is visible, featuring a sectional sofa and a television mounted on the wall.

5 out of 5 average rating, 254 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

4.95 out of 5 average rating, 103 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in Avondale

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

4.96 out of 5 average rating, 338 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

4.8 out of 5 average rating, 160 reviews

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Lincoln Park

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Apartment in West Lake View

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.

4.94 out of 5 average rating, 175 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!

4.88 out of 5 average rating, 169 reviews

A modern bathroom is highlighted by a spacious walk-in shower featuring vibrant blue tiles and gold fixtures. A stylish, illuminated mirror above a contemporary vanity with blue cabinetry is visible, complemented by elegant marble flooring throughout the space.

Home in Lake View

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

4.82 out of 5 average rating, 116 reviews

The kitchen features white cabinetry and a stainless steel refrigerator. A two-burner stove and sink are visible, along with a microwave and coffee maker on the countertop. A wooden dining table is paired with metal chairs, providing a casual dining space.

Apartment in Lake View

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

4.91 out of 5 average rating, 123 reviews

A welcoming living space is bathed in natural light, featuring large windows adorned with elegant curtains. A plush, tufted sofa with decorative pillows invites relaxation. Neutral walls complement the modern décor, which includes a sleek table and artwork, creating a harmonious atmosphere.

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

4.94 out of 5 average rating, 115 reviews

The entrance is characterized by elegant stone steps leading to two ornate wooden doors. Flanking the entry, flower boxes add a touch of color. The structure features large windows, allowing natural light to brighten the facade, and is complemented by a decorative wrought-iron fence.

Apartment in Lake View

The Wrigley Flats | Chicago Vacation Rental

The Wrigley Flats is a unique Chicago vacation rental located 4 blocks south of Wrigley Field in city’s most sought after north side neighborhood---Wrigleyville! Our 3 bedroom | 1 bathroom flat can be rented for a weekend getaway, a week long vacation or an extended stay. Close proximity to Chicago’s lakefront, vibrant nightlife, the eclectic dining scene & of course Wrigley Field; it’s no wonder visitors flock here to get a taste of something amazing!

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

4.96 out of 5 average rating, 280 reviews

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Irving Park

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Chicago vacation rentals

Free parking on premises

Stay near Chicago's top sights

O'Hare International Airport122 locals recommend

Wrigley Field1,004 locals recommend

Boystown92 locals recommend

Logan Square174 locals recommend

United Center200 locals recommend

Millennium Park1,243 locals recommend

Chicago fishing vacation rentals

4.97 out of 5 average rating, 487 reviews

A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.

Apartment in Evanston

Charming, Sunny Apartment with Backyard Garden

4.93 out of 5 average rating, 153 reviews

An inviting living area showcases a light-colored sectional sofa paired with a matching ottoman. A dark coffee table sits nearby, and a warm area rug lies underfoot. A bookshelf filled with books lines the wall, while soft lighting highlights the natural warmth of the wood flooring.

Home in Lake View

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

4.83 out of 5 average rating, 442 reviews

A cozy living area is highlighted by a red accent wall and brick details. A comfortable blue sofa faces a mounted television, with a striped chair nearby. A mirror and decorative plant are positioned against a stylish cabinet, complementing the space's inviting layout.

Apartment in Lake View

Lakeview Charmer -with parking!

4.95 out of 5 average rating, 111 reviews

A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.

Bungalow in Lake View

Chicago Bootlegger House Sleeps 10-20

Apartment in East Rogers Park

An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.

4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

4.89 out of 5 average rating, 794 reviews

A rustic kitchen and dining area features wooden cabinets and a large island with stainless steel appliances. A dining table with six wooden chairs is illuminated by natural light from the large windows. Exposed brick walls add character to the space.

Loft in Lake View

2bd/2bath Urban Loft w/ 2 pkg spots 1 blk to train

4.98 out of 5 average rating, 270 reviews

A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.

Condo in Uptown

Near Lake Michigan & Wrigley Field

4.84 out of 5 average rating, 152 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

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Apartment rentals in Chicago

4.97 out of 5 average rating, 106 reviews

A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.

Apartment in Avondale

Lovely 2bedroom 1bath Apt and outdoor seating.

4.83 out of 5 average rating, 184 reviews

A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.

Apartment in Chinatown

New apartment

Apartment in East Rogers Park

A small entryway is illuminated by soft natural light filtering through a lace curtain. A vase of white roses sits atop a white table, with a radiator located below it. Beige walls with a minimalist aesthetic offer a warm welcome.

4.84 out of 5 average rating, 386 reviews

Cozy Garden Unit In Edgewater

4.86 out of 5 average rating, 542 reviews

The kitchen includes modern appliances, white cabinetry, and a tiled floor. A view into the adjoining living area reveals a comfortable seating arrangement. Natural light enters through a nearby window, enhancing the functional kitchen space.

Apartment in Avondale

Logan Square Lookout

4.98 out of 5 average rating, 210 reviews

A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.

Apartment in Chicago

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Apartment in Roscoe Village

A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.

4.97 out of 5 average rating, 145 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

Apartment in Logan Square

A modern living area features a light-colored sofa adorned with decorative pillows. A small coffee table sits at the center, complemented by a decorative globe and a plant. Two windows allow natural light, while a mirror and dining area are visible in the background.

4.83 out of 5 average rating, 262 reviews

BERNARD CHATEAU - LOGAN SQUARE

4.97 out of 5 average rating, 108 reviews

A comfortable seating area features a wooden sofa adorned with checkered cushions. A coffee table sits in front, while a light fixture mounted on the wall adds illumination. A large artwork depicting a cityscape with the Eiffel Tower is displayed above the sofa.

Apartment in Evanston

Charming one bedroom apartment

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Homes in Chicago

4.89 out of 5 average rating, 18 reviews

The exterior of the bungalow features a modern white facade with large windows, allowing for natural light. A covered porch is visible, offering shaded seating space. Surrounding trees cast gentle shadows on the ground, enhancing the tranquility of the setting.

Home in Homewood

Dream Stay - Modern Bungalow Near Downtown

4.81 out of 5 average rating, 193 reviews

The image presents a two-story home with framed cedar bevel siding. A welcoming front porch features wooden railings and steps leading to the entrance. Surrounding greenery adds a natural touch, while the well-maintained pathway and lawn contribute to the property’s inviting exterior.

Home in Blue Island

Warm and comfortable inviting Suburban home !

4.73 out of 5 average rating, 124 reviews

A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.

Home in Markham

The Country Life! Entire House.

4.71 out of 5 average rating, 42 reviews

The living area features a modern gray sofa with yellow and gold accent pillows, complemented by two blue armchairs. A low white coffee table sits atop a patterned black and white rug. Natural light enters through large windows, illuminating a wall-mounted TV and a decorative plant.

Home in Homewood

Horizon - 4 BRs, 2 BA Game Room & Gym

4.79 out of 5 average rating, 39 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. A modern sectional sofa sits adjacent to a glass coffee table, while a dining area with elegant chairs and a chandelier completes the setting. Unique wall art adds character to the space.

Home in Logan Square

5BR/4BA Home - Theatre, Hot Tub, Sauna, Rooftop!

4.85 out of 5 average rating, 100 reviews

A charming house features a sloping roof and a light-colored exterior, complemented by a welcoming front porch. Outdoor seating is arranged on a spacious deck, surrounded by a wooden railing. Warm lights are strung overhead, creating an inviting atmosphere in the surrounding grassy area.

Home in Des Plaines

Cozy Home by O'Hare + EV Plug

4.92 out of 5 average rating, 103 reviews

The charming exterior of a two-story brick home features a welcoming front porch with a green door and large windows framed by black shutters. Lush greenery and seasonal decorations, including a pumpkin, enhance the inviting curb appeal.

Home in Munster

Cozy House with Gazebo