Chicago Rentals
From $275 per night (USD)VRBO
Edgewater Glen 3BD Cozy Retreat Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience a delightful stay in this 3BR, 1.5BA home in Edgewater. Start your morning with coffee in the shar ...
From $275 per night (USD)VRBO
From $135 per night (USD)VRBO
Serene 2-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bedroom apartment. The adorable space features two queen beds, perfect for a ...
From $135 per night (USD)VRBO
From $307 per night (USD)VRBO
Chic River North Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to your stylish home base in the heart of River North, one of Chicago’s most vibrant and walkable neig ...
From $307 per night (USD)VRBO
From $247 per night (USD)VRBO
Spacious 4-bedroom apartment in gorgeous Chicago with AC and gym
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Discover the beauty of Chicago from this 4-bedroom apartment. The space features a queen bed, a twin bed, and two bunk b ...
From $247 per night (USD)VRBO
From $217 per night (USD)VRBO
Pet-Friendly Uptown Chicago Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
Summary: 2 bedroom Unit in Uptown Chicago The Space: 2 bedroom home with 2 bathrooms that sleeps 11. Bed sizes a ...
From $217 per night (USD)VRBO
From $333 per night (USD)VRBO
All Season Chicago Haven Near United Center Rush Hospital and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this charming apartment in Chicago. With two comfortable bedrooms featuring a king and a queen bed, guests ca ...
From $333 per night (USD)VRBO
From $170 per night (USD)VRBO
Prime 3BR/2BA in the Heart of Chicago. 10 mins to Dine & Downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy a peaceful stay at this 3-bedroom apartment in Chicago. The space features two queen beds and one full bed, provid ...
From $170 per night (USD)VRBO
From $348 per night (USD)VRBO
3BR Retreat Perfect for Professionals and Families in South Shore/ Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your home away from home! This fully renovated 3-bedroom, 2-bathroom apartment offers modern comfort in the h ...
From $348 per night (USD)VRBO
From $348 per night (USD)VRBO
Chic Luxe Spa Retreat - Light Filled+King Bed+Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light fr ...
From $348 per night (USD)VRBO
From $420 per night (USD)VRBO
Patio • Workspace • Dog Friendly • Free Street Parking • Train Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll fall in love with this garden apartment that offers easy access to both the O'Hare airport & the heart of Chicago ...
From $420 per night (USD)VRBO
From $394 per night (USD)VRBO
Sleek Avondale Condo Spa Bath King Bed +Queen bed +Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern meets mmm-hmm in this 2BR Avondale gem. King & queen beds? Check. Spa bath with rain shower & jets? Oh yes. Strea ...
From $394 per night (USD)VRBO
From $151 per night (USD)VRBO
Cozy 1-bedroom apartment in beautiful West Loop, in-unit laundry + pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy up in this serene space in one of Chicago's most beautiful neighborhoods, the West Loop. This superb one-bedroom is ...
From $151 per night (USD)VRBO
From $148 per night (USD)VRBO
Feel at Home while Exploring Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably in Chicago at this 2-bedroom apartment. The space features one queen bed and one twin bed, plus a cozy ...
From $148 per night (USD)VRBO
From $379 per night (USD)VRBO
Spacious West Loop Retreat UnitedCenter & Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bright and spacious top-floor condo in a 2-unit building, on a quiet and safe residential street. Perfect for couples, ...
From $379 per night (USD)VRBO
From $294 per night (USD)VRBO
Peaceful 3-bedroom apartment in charming Chicago Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This 3-bedroom apartment is perfect for your escape to Chicago. Inside, guests find a wonderful mix of comfort with a qu ...
From $294 per night (USD)VRBO
From $137 per night (USD)VRBO
Modern Garden Apartment w/ New Kitchen + Bathroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our newly renovated garden apartment in Irving Park! This private-entry unit features 2 cozy bedrooms, a bran ...
From $137 per night (USD)VRBO
From $438 per night (USD)VRBO
Westloop Spacious 4 bdrm Duplex with parking & workout area
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Centrally located duplex-down, ideal for families and groups of up to 10. Features 4 bedrooms (2 King, 2 Queen), 3 full ...
From $438 per night (USD)VRBO
From $101 per night (USD)VRBO
Cozy 1-bedroom garden apartment in W Lakeview/Wrigley/Roscoe Village/Fast WIFI
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bright 1BR & 1 Bath in Prime Lakeview — great for long stays, remote work, or city trips! What You’ll Love: • Fast WiFi ...
From $101 per night (USD)VRBO
From $252 per night (USD)VRBO
Modern Edgewater Apartment: 2BD 2BA with Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the charm of Chicago's Edgewater neighborhood from this modern retreat just steps from the Granvill ...
From $252 per night (USD)VRBO
From $340 per night (USD)VRBO
Beautiful condo with elevator right into your unit in North Kenwood Hyde Park.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom condo in Chicago. The space features one king bed and two queen beds, perfect for f ...
From $340 per night (USD)VRBO
From $186 per night (USD)VRBO
River North / Mag Mile, Lake and City Views, 43rd Floor Condo, Parking Included!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In this breathtaking NE corner apartment at Huron and Wabash, every window frames the mesmerizing Chicago Skyline and La ...
From $186 per night (USD)VRBO
From $183 per night (USD)VRBO
2-bedroom house in terrific Chicago neighborhood walking distance to everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Get ready to relax in this 2-bedroom house in Chicago. The space features a queen bed, a twin bed, and a comfy sofa bed, ...
From $183 per night (USD)VRBO
From $282 per night (USD)VRBO
Stay near Wrigley Field! Spacious 3BD Penthouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your spacious Lakeview retreat just steps from Wrigley Field! Catch a Cubs game, explore the neighb ...
From $282 per night (USD)VRBO
From $280 per night (USD)VRBO
Lakeview 3BD 2BA Penthouse near Wrigley Field!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the best of Chicago from this modern 3-bed, 2-bath Lakeview retreat, just steps from Wrigley Field, ...
From $280 per night (USD)VRBO
From $636 per night (USD)VRBO
Charming 6BD Retreat - Steps Away from Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to our *NEW* charming and spacious 6BD home—perfect for large groups seeking comfort and convenience. Just a few ...
From $636 per night (USD)VRBO
From $72 per night (USD)VRBO
Logan Square SRO Hotel Room 209
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully furnished private hotel room in a perfect Logan Square location! This room shares a bathroom with one other room a ...
From $72 per night (USD)VRBO
From $333 per night (USD)VRBO
Escape to Springfield Serenity—a stylish two-bedroom retreat designed for relaxation and play. Enjoy a peaceful meditation corner, cozy living, and a nostalgic Pac-Man arcade for the perfect balance of calm and fun.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Springfield Serenity, a modern two-bedroom retreat designed for calm and connection. Unwind in the serene med ...
From $333 per night (USD)VRBO
From $255 per night (USD)VRBO
Cozy Retreat in Hyde Park with In Unit Laundry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
There are about 5 steps that you have to go down to get to the apartment. This beautifully designed apartment features ...
From $255 per night (USD)VRBO
From $288 per night (USD)VRBO
Wonderful 2-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the beauty of Chicago from this 2-bedroom apartment. This fabulous rental offers heating, AC, a hair dryer, and ...
From $288 per night (USD)VRBO
From $217 per night (USD)VRBO
Private Romantic Retreat for Two • Luxury Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape the ordinary and step into a curated romantic retreat designed exclusively for adult couples (25+). This is more ...
From $217 per night (USD)VRBO
From $435 per night (USD)VRBO
3 Bedroom Apartment, 15 min drive to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to your warm and inviting 3-bedroom apartment, the perfect home base for families, friends, or business traveler ...
From $435 per night (USD)VRBO
From $308 per night (USD)VRBO
Beautiful Chicago Greystone
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Ce ...
From $308 per night (USD)VRBO
From $532 per night (USD)VRBO
Fantastic 4-bedroom apartment with AC in charming Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Your home away from home in Chicago with 4 bedrooms. This wonderful apartment offers plenty of space with 4 full beds an ...
From $532 per night (USD)VRBO
From $110 per night (USD)VRBO
Private Cozy Cottage House in Lincoln Park w/ Porch
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About this space Private coach house in the heart of Lincoln Park. Updated and light-filled with vaulted ceilings, skyli ...
From $110 per night (USD)VRBO
From $98 per night (USD)VRBO
Luxury New Construction Condo - Chicago Living at Its Finest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Your Modern Chicago Retreat Step into this stunning brand-new construction condo, where modern design meets ...
From $98 per night (USD)VRBO
From $760 per night (USD)VRBO
The Jackpot - Hot Tub, Cinema, Game Room, Fire Pit, Bar, Garage - Sleeps 14
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to The Jackpot — a one-of-a-kind luxury home in Chicago designed for groups who want more than just a place to s ...
From $760 per night (USD)VRBO
From $418 per night (USD)VRBO
Living like a local in Bronzeville chicago with massive roof deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Chicago like a local in this 3-bedroom apartment. The space features three comfortable queen beds and two bat ...
From $418 per night (USD)VRBO
From $417 per night (USD)VRBO
Luxurious living in Bronzeville Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Your cozy getaway awaits in Chicago at this beautiful apartment. With three bedrooms featuring two queen beds and a futo ...
From $417 per night (USD)VRBO
From $556 per night (USD)VRBO
Movie-Themed Home w/ Theater - Sleeps 12 - 4BR
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to a Private Movie Experience in this 3-story home - just 10 miles to downtown! Step into a one-of-a-kind movie ...
From $556 per night (USD)VRBO
From $273 per night (USD)VRBO
Stunning Fully Furnished 3BR/3BA Mid-Century Modern Duplex in Historic Old Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO YOUR OLD TOWN RETREAT Step into modern Chicago living with historic charm. This exquisitely appointed 1,700 ...
From $273 per night (USD)VRBO
From $153 per night (USD)VRBO
Bucktown/Wicker Park 3BR pet friendly w/parking - Upstairs Unit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
New Listing - Charming 3BR 1 BTH fully furnished upstairs apartment in Bucktown/Wicker Park area |Pet Friendly | In-Unit ...
From $153 per night (USD)VRBO
From $199 per night (USD)VRBO
Spacious 3-bedroom retreat in West Logan with modern amenities, perfect for families looking to relax and explore vibrant Logan Square.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This spacious and stylish 3-bedroom apartment is perfect for family or groups. With its own private entrance. Enjoy free ...
From $199 per night (USD)VRBO
From $428 per night (USD)VRBO
Stylish 2 Bedroom Aparment with Games and Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish 2BR Apartment w/ Modern Kitchen + Free Parking near Downtown Relax, play, and feel at home in this stylish 2-b ...
From $428 per night (USD)VRBO
From $774 per night (USD)VRBO
Stunning 3-Story Home with Chef's Kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Hemly House — a stunning 3-story Chicago home designed for groups who want space, style, and comfort. Featuri ...
From $774 per night (USD)VRBO
From $142 per night (USD)VRBO
Modern 2B Irving Park Gem / Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Spacious, newly renovated 2BR in Irving Park—perfect for families and groups up to 5. Enjoy a bright living area, full k ...
From $142 per night (USD)VRBO
From $239 per night (USD)VRBO
Spacious 2 bedroom Apt + FREE Parking, Close to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Modern, spacious apartment w/ FREE parking-just 15 min to Downtown. Enjoy an open layout, fully equipped kitchen, cozy l ...
From $239 per night (USD)VRBO
From $95 per night (USD)VRBO
Modern 3BR/2BA South Shore Gem Near Obama Presidential Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this spacious and comfortable 3-bedroom, 2-full-bath second-floor apartment located in the vibrant South Shor ...
From $95 per night (USD)VRBO
From $418 per night (USD)VRBO
Luxury Living in Bronzeville with Oversized Rooftop.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a peaceful stay at this 3-bedroom building in Chicago. The charming space features three queen beds, offering plen ...
From $418 per night (USD)VRBO
From $477 per night (USD)VRBO
Location, large luxury house - safe and close to everything.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Chicago from this 3-bedroom luxury house. Guests will find a tranquil space featuring one king be ...
From $477 per night (USD)VRBO
From $531 per night (USD)VRBO
Luxury 3-bedroom house with AC in vibrant Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Chicago is waiting for you at this luxury large 3-bedroom house. Inside, guests find a comfortable king bed, a cozy quee ...
From $531 per night (USD)VRBO
From $224 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $224 per night (USD)VRBO
From $344 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This smoke-free hotel features a fitness center and barbecue grills. Air-conditioned accommodations at this hotel offer ...
From $344 per night (USD)VRBO
From $385 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $385 per night (USD)VRBO
From $331 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $331 per night (USD)VRBO
From $300 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $300 per night (USD)VRBO
From $300 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $300 per night (USD)VRBO
From $378 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $378 per night (USD)VRBO
From $409 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $409 per night (USD)VRBO
From $415 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $415 per night (USD)VRBO
From $301 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $301 per night (USD)VRBO
From $224 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $224 per night (USD)VRBO
From $216 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $216 per night (USD)VRBO
From $287 per night (USD)VRBO
Plymouth Collection: Top Floor with Gym & Rooftop!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $287 per night (USD)VRBO
From $296 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $296 per night (USD)VRBO
From $224 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $224 per night (USD)VRBO
From $219 per night (USD)VRBO
Plymouth Collection: Top Floor with Gym & Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $219 per night (USD)VRBO
From $385 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $385 per night (USD)VRBO
From $300 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $300 per night (USD)VRBO
From $300 per night (USD)VRBO
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $300 per night (USD)VRBO
From $385 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $385 per night (USD)VRBO
From $385 per night (USD)VRBO
Plymouth Collection: 3BD 2BA with Gym & Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...
From $385 per night (USD)VRBO
From $371 per night (USD)VRBO
Plymouth Collection: Top Floor w/ Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $371 per night (USD)VRBO
From $415 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $415 per night (USD)VRBO
From $196 per night (USD)VRBO
Plymouth Collection: 2BD High Floor w/ Gym,Rooftop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated ...
From $196 per night (USD)VRBO
From $336 per night (USD)VRBO
Plymouth Collection: 4BD 3BA High Floor with Gym
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $336 per night (USD)VRBO
From $409 per night (USD)VRBO
Plymouth Collection: 4BD 3BA with Rooftop & Lobby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of d ...
From $409 per night (USD)VRBO
From $325 per night (USD)VRBO
Modern Condo Retreat in Logan Square Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a comfortable and stylish stay in this newly remodeled condo located in the heart of Logan Square. Designed with b ...
From $325 per night (USD)VRBO
From $245 per night (USD)VRBO
3BR Family Getaway w/King Suite + Games
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious Chicago family home in Irving Park with easy access to O’Hare Airport, Wrigley Field, and downtown Chicago. Loc ...
From $245 per night (USD)VRBO
From $201 per night (USD)VRBO
Modern Chicago 2BR Retreat | Parking + Patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to this beautifully furnished 2-bedroom, 2-bathroom apartment in Chicago's desirable Bridgeport/Chinatown area. ...
From $201 per night (USD)VRBO
From $220 per night (USD)VRBO
Chicago Getaway: Family-Friendly 2BD 2BA Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience Chicago like a local from this modern retreat in the heart of Tri-Taylor. Start your morning with c ...
From $220 per night (USD)VRBO
From $104 per night (USD)VRBO
Beautiful artist loft immersed in art, plants, and a collection of books
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to this adorable apartment in picturesque Chicago. Guests enjoy a cozy one-bedroom space that feels like a home a ...
From $104 per night (USD)VRBO
From $258 per night (USD)VRBO
MTR~TopFloor~Patio~PetFriendly~FreeParking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our stylish top floor three-bedroom apartment in Roscoe Village neighborhood of Chicago! The unit offers the ...
From $258 per night (USD)VRBO
From $258 per night (USD)VRBO
MTR~Patio~PetFriendly~FreeParking~WalkingTreadmill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our stylish three-bedroom apartment in Roscoe Village neighborhood of Chicago! The unit offers the following ...
From $258 per night (USD)VRBO
From $256 per night (USD)VRBO
MTR-Gym Gear-Garage Parking-Patio - Work Space
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home-away-from-home in Chicago’s Irving Park—ideal for travel professionals, medical staff, and extended ...
From $256 per night (USD)VRBO
From $400 per night (USD)VRBO
MTR-PetFriendly-FreeParking-WalkingTreadmill
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our stylish four-bedroom apartment in the Lincoln Park neighborhood of Chicago! The unit offers the following ...
From $400 per night (USD)VRBO
From $398 per night (USD)VRBO
MTR - Walk to Lake - Steps to Dining, Zoo & DePaul
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our stylish four-bedroom apartment in the Lincoln Park neighborhood of Chicago! The unit offers the following ...
From $398 per night (USD)VRBO
From $419 per night (USD)VRBO
MTR in the heart of Lincoln Park with Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our stylish four-bedroom apartment in the Lincoln Park neighborhood of Chicago! The unit offers the following ...
From $419 per night (USD)VRBO
From $176 per night (USD)VRBO
Luxury Furnished 2-bedroom Loft- walking distance to UIC and Medical district
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Modern Furnished 2BR/1BA luxury loft in University Village. Minutes from Downtown, Illinois Medical District, UIC, Unive ...
From $176 per night (USD)VRBO
From $384 per night (USD)VRBO
Family style pet friendly Pilsen apartment with park/playground access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Full apartment featuring direct access to Jefferson park for kids and pets. Located in-between the heart of Pilsen, Chin ...
From $384 per night (USD)VRBO
From $120 per night (USD)VRBO
Bright Top-Floor 2BR with Private Yard Near O’Hare
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Chicago’s quiet Dunning–Schorsch Village at this charming and comfortable apartment. Featuring two inviting be ...
From $120 per night (USD)VRBO
From $303 per night (USD)VRBO
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple di ...
From $303 per night (USD)VRBO
From $383 per night (USD)VRBO
Splendid Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and f ...
From $383 per night (USD)VRBO
From $336 per night (USD)VRBO
Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: [NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The ...
From $336 per night (USD)VRBO
From $365 per night (USD)VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: [NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The ...
From $365 per night (USD)VRBO
From $320 per night (USD)VRBO
3BR near U Chicago and Obama Center, Easy Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your bright and spacious 3-bedroom, 1-bath second-floor home in the heart of Woodlawn—just minutes from the U ...
From $320 per night (USD)VRBO
From $226 per night (USD)VRBO
2BR Chicago Getaway, Central AC Cozy & Family Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable 2BR/1BA home in Rogers Park/Loyola, designed for a relaxing and convenient stay. Enjoy comfo ...
From $226 per night (USD)VRBO
From $184 per night (USD)VRBO
Rogers Park Cozy 1BR Central AC Fast WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our cozy and thoughtfully designed 1BR/1BA home in Rogers Park/Loyola, perfect for relaxing stays, work trips ...
From $184 per night (USD)VRBO
From $1447 per night (USD)VRBO
Sun-Soaked West Loop Penthouse - Private Rooftop/3 Full Baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
This Sun Soaked West Loop Penthouse is the perfect home away from home. With it's expertly designed living areas and all ...
From $1447 per night (USD)VRBO
From $233 per night (USD)VRBO
Renovated 3 Bedroom Chicago Downtown Pilsen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The Space: 3 bed room apartment that sleeps 10 people. Room arrangement "Bedroom 1" 2 Double beds "Bedroom 2" Qu ...
From $233 per night (USD)VRBO
From $595 per night (USD)VRBO
3-bedroom + loft house next to downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This stylish oasis combines high-end finishes with thoughtful touches, kitchen with a waterfall quartz countertop and a ...
From $595 per night (USD)VRBO