Chicago vacation rentals

Apartment in Lincoln Park

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

5 out of 5 average rating, 264 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.

A vintage brick building features an inviting entrance with a maroon awning. The path is framed by well-maintained greenery, leading to dual wooden doors. Large windows are positioned above, allowing natural light to illuminate the space.

4.91 out of 5 average rating, 429 reviews

The Grotto of Logan Square

Garden unit, great for a small group looking for a base while they explore the city. 10 min walk from Logan Square Blue Line, restaurants, galleries, coffee shops and clubs. Explore the city from one of its best neighborhoods! In your downtime the space offers several chicago guide books and magazines. There is a Fire stick in the TV that has most major media apps installed. The alarm clock is also a speaker for your phone to plug into. Please make sure you read the amenities and house manual.

Apartment in Magnificent Mile

4.98 out of 5 average rating, 161 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.

4.97 out of 5 average rating, 163 reviews

A modern bathroom showcases a mid-century modern vanity in natural wood with two drawers. Above it, a round mirror is complemented by a pendant light. A white toilet is positioned nearby. White hexagon tiles cover the floor, while a skylight fills the room with natural light.

Apartment in Avondale

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.97 out of 5 average rating, 115 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Apartment in Humboldt Park

A spacious living area is highlighted by sloped ceilings and wooden beams. A comfortable sectional sofa and a coffee table are nestled on a well-kept area rug. A television is positioned against the wall, while natural light filters in through two skylights.

4.99 out of 5 average rating, 140 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Apartment in Wrigleyville

A living area is presented with a stylish couch adorned with textured pillows. A modern floor lamp provides soft illumination beside a unique armchair, characterized by striped backrest and a red cushion. An artistic skull print is displayed on the wall above a round side table.

4.98 out of 5 average rating, 104 reviews

No Place Like Gnome at Wrigley

This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in all of rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a five minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's about a ten minute walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

4.9 out of 5 average rating, 309 reviews

The exterior view of a vintage bungalow is captured, showcasing its brick façade and welcoming entryway. Green shrubs flank the front steps, while a flag adorns the porch. A spacious lawn is visible, and neighboring houses create a sense of a residential neighborhood.

Apartment in Berwyn

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

4.99 out of 5 average rating, 233 reviews

A modern living area features a green velvet couch and a round wooden coffee table atop a patterned area rug. A television is positioned on a media console, with natural light coming through multiple windows. Artwork adorns the walls, adding character to the space.

Apartment in Chicago

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

4.94 out of 5 average rating, 129 reviews

Guest suite in Avondale

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

4.92 out of 5 average rating, 349 reviews

A cozy enclosed porch features large windows allowing natural light to fill the space. Two teal lounge chairs are positioned beside a small table, with colorful decorative elements scattered throughout. A patterned rug adds warmth to the floor, creating a relaxed atmosphere.

Condo in Logan Square

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Guest suite in North Center

A foosball table is positioned in the foreground, featuring uniform rows of players. The players are crafted from black with gold accents, arranged to create a competitive atmosphere. Bright light filters in from a nearby doorway, illuminating the game area.

4.97 out of 5 average rating, 121 reviews

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

O'Hare International Airport14 locals recommend

Wrigley Field158 locals recommend

United Center50 locals recommend

Millennium Park213 locals recommend

Navy Pier274 locals recommend

University of Chicago14 locals recommend

Chicago fishing vacation rentals

4.87 out of 5 average rating, 240 reviews

A comfortable living area features a plush sectional sofa and a cozy armchair. A wooden coffee table is positioned centrally, while a television is displayed on a dark media unit. Natural light enters through multiple windows, highlighting the room's stone accent wall.

Condo in Woodlawn

A Stones Throw from U Chicago South Campus!

4.97 out of 5 average rating, 502 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

4.9 out of 5 average rating, 367 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 Uptown

Private 3rd Floor Apartment

Townhouse in Lincoln Park

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, 277 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

5 out of 5 average rating, 108 reviews

A well-maintained gray exterior with white trim is presented. Surrounded by a wooden fence, the yard features a grassy area and is shaded by trees. A sunny sky with scattered clouds adds to the inviting ambiance of the outdoor space.

Home in Evanston

Larimer Park Carriage House

Condo in East Rogers Park

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

4.93 out of 5 average rating, 244 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

4.85 out of 5 average rating, 157 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

4.97 out of 5 average rating, 299 reviews

A spacious living area is furnished with a light-colored sofa, two armchairs, and an entertainment unit containing books. Soft lighting from a lamp creates a warm atmosphere. A geometric area rug adds visual interest to the carpeted floor. The sloped ceiling enhances the cozy feel of the space.

Apartment in Uptown

Cozy loft in Chicago's Uptown

Show all

Dog friendly vacation rentals in Chicago

Apartment in Roscoe Village

A living area features a comfortable sofa adorned with decorative pillows, complemented by a sleek chair. A dining space with a round table and chairs is visible through the open entrance, while warm wood accents enhance the inviting atmosphere.

4.96 out of 5 average rating, 303 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Guest suite in Portage Park

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 423 reviews

Peaceful Portage Park Apartment

4.97 out of 5 average rating, 123 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, 146 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

Superhost

A bright living area features large windows allowing natural light to fill the space. A turquoise sofa and a gray couch are complemented by colorful cushions. A wooden coffee table rests on a patterned rug, surrounded by decorative plants and modern lighting.

Apartment in Irving Park

4.79 out of 5 average rating, 145 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

4.91 out of 5 average rating, 503 reviews

A modern kitchen showcases dark wood cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop extends into a bar area with three metal stools. A microwave and kettle are placed on the counter, illuminated by overhead lighting.

Guest suite in Wood Dale

The Deer Suite

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.

4.96 out of 5 average rating, 127 reviews

Garden Unit Getaway-Bucktown

4.9 out of 5 average rating, 126 reviews

A bright living room is featured, displaying a blue sofa and yellow chairs arranged around a coffee table. A large clock adorns the blue accent wall, while natural light enters through the window. A plant adds a touch of greenery, completing the inviting space.

Condo in Berwyn

Picturesque Apartment in Berwyn

Show all

Family friendly vacation rentals in Chicago

A serene bedroom features a spacious bed adorned with neutral linens and colorful pillows. Natural light enters through two windows, highlighting a small desk and a variety of indoor plants. Wall-mounted lights and framed artwork add a touch of style.

4.96 out of 5 average rating, 447 reviews

King Bed, Huge Spa Shower, Dining Destination

Guest suite in Lincoln Square

A spacious backyard is depicted, featuring a well-maintained lawn framed by lush greenery and trees. A wooden deck attached to the house is visible, along with a fenced perimeter providing privacy. Sunshine illuminates the area, creating a peaceful outdoor space.

4.97 out of 5 average rating, 428 reviews

Private suite in Lincoln Square

4.94 out of 5 average rating, 299 reviews

A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.

Apartment in Blue Island

Charming Unique 2 Bdrm Apartment in Victorian Home

4.88 out of 5 average rating, 250 reviews

A well-maintained outdoor space is presented, featuring a manicured lawn surrounded by tall greenery and colorful flower beds. A two-story structure with a wooden deck is visible, along with a walkway leading through the garden, creating an inviting environment for relaxation.

Apartment in Chicago

Historic Coach House Cottage

Guest suite in Lincoln Square

A bright kitchen features orange walls and white cabinetry. A white refrigerator and a black gas stove are positioned alongside a kitchen sink. A small dining table with a checkered tablecloth is set for two. Colorful artwork and a floral curtain enhance the inviting space.

4.92 out of 5 average rating, 478 reviews

Cozy, Quiet, Garden Getaway!

4.91 out of 5 average rating, 279 reviews

An open space is divided by sheer curtains, showcasing a king size bed with neutral bedding and a cozy queen size bed in the background. A sectional couch and a dining area with a table are visible, along with a complete kitchen featuring modern appliances.

Loft in Brighton Park

Entire place with free parking.

4.96 out of 5 average rating, 346 reviews

A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park