Chicago Rentals
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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $115 per night (USD)VRBO
Western Logan Square near Healy Metra Stop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Please contact me with your reservation dates of less than 31 night. T ...
From $115 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
From $399 per night (USD)VRBO
Beautiful 2-bedroom apartment near united center/few minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this charming apartment in Chicago. With two cozy bedrooms featuring 3 queen beds, guests can enjoy a restful ...
From $399 per night (USD)VRBO
From $435 per night (USD)VRBO
Spacious 5-bedroomDuplex in lovely South Shore with AC
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious 5-Bedroom, 2-Bath Updated Duplex in South Shore | Chicago Looking for a comfortable Chicago stay with plent ...
From $435 per night (USD)VRBO
From $490 per night (USD)VRBO
Spacious 7-bedroom house in Chicago with 2 Car Garage/parking Pod/Mins to DT
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 14
Discover the beauty of Chicago from this 7-bedroom house. Each room features a comfortable queen bed, perfect for a rest ...
From $490 per night (USD)VRBO
From $302 per night (USD)VRBO
2 BR Apt. — Near U Chicago Campus + the Lakefront !
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your Chicago adventure begins at this 2-bedroom apartment. Inside, guests find two comfortable queen beds and a beautifu ...
From $302 per night (USD)VRBO
From $315 per night (USD)VRBO
A 3-bedroom, 2-bathroom residence that provides ample space and comfort.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chicago adventure begins at this 3-bedroom apartment. Step into a nice and serene space where guests can relax afte ...
From $315 per night (USD)VRBO
From $182 per night (USD)VRBO
The Huron Loft | Near Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay in the heart of Chicago at The Huron Loft, perfectly located near the Magnificent Mile, Michigan Avenue, ...
From $182 per night (USD)VRBO
From $322 per night (USD)VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city a ...
From $322 per night (USD)VRBO
From $257 per night (USD)VRBO
Rooftop Reverie | Prime Location - Modern-Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern 3BR/2BA condo in the heart of vibrant Pilsen, a prime and centrally located neighborhood with quick access to dow ...
From $257 per night (USD)VRBO
From $246 per night (USD)VRBO
Cozy Chicago Smoke Ok 3BR Suite Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your urban escape in Chicago’s vibrant South Loop neighborhood! This stunning 3-bedroom, 2-bathroom apartment ...
From $246 per night (USD)VRBO
From $132 per night (USD)VRBO
Comfy 3Bdrm near LSD,Obama Center, UIC, Sci Museum
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
South Shore located along Chicago’s shoreline, with stunning views of Lake Michigan. This location is a perfect stay. G ...
From $132 per night (USD)VRBO
From $561 per night (USD)VRBO
Gold Coast, Downtown Chicago, Sleeps 20
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 20
Summary: Gold Coast Jumbo Duplex-Down LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad, w ...
From $561 per night (USD)VRBO
From $308 per night (USD)VRBO
River West 4BD Home: Perfect for Families & Groups
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning 4-bedroom retreat in Chicago's River West neighborhood. Walk to local cafés and brewer ...
From $308 per night (USD)VRBO
From $218 per night (USD)VRBO
Pilsen 2BA Condo Minutes from Chicago Attractions
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience Chicago like a local from this beautifully renovated retreat in the heart of Pilsen. Wake up in a s ...
From $218 per night (USD)VRBO
From $259 per night (USD)VRBO
Serene Avondale Triangle Apartment I Near Wrigley/Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Savor the privacy, comfort, and location in this Avondale apartment. Steps to the Belmont Blue Line train from O'Hare an ...
From $259 per night (USD)VRBO
From $424 per night (USD)VRBO
Wicker Park 4BD Home: Parking, Theater, & Rooftop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Summary: Elevate your Chicago getaway in this luxurious Wicker Park retreat. Cook in a chef's kitchen, unwind in your p ...
From $424 per night (USD)VRBO
From $347 per night (USD)VRBO
Amazing Penthouse: Views, Hot Tub, Cold Plunge!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Experience city living in this stylish 3BD/3BA duplex penthouse in the heart of Wicker Park! Just a 2-minute w ...
From $347 per night (USD)VRBO
From $544 per night (USD)VRBO
Designer Oasis - Sauna, Hot Tub, Patios, Game room
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Experience Chicago in style from this one-of-a-kind Wicker Park retreat. Spend your days exploring award-winni ...
From $544 per night (USD)VRBO
From $266 per night (USD)VRBO
United Center 3BD Apt with Parking and Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover this modern 3-bed apartment, ideally situated near Chicago's United Center. This spacious retreat off ...
From $266 per night (USD)VRBO
From $394 per night (USD)VRBO
Super Paradise Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern and luxurious, open plan, LARGE full equipped back yard also included, located near Midway Airport and 12 minutes ...
From $394 per night (USD)VRBO
From $1839 per night (USD)VRBO
5,000 Sq Ft Luxury Chicago Loft - Prime River North Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to an incredible 5,000-square-foot loft in the heart of Chicago’s River North neighborhood. Designed for groups ...
From $1839 per night (USD)VRBO
From $926 per night (USD)VRBO
Luxury Duplex • 4 bedrooms, 3 Bath• Private Speakeasy• Outdoor Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Experience Casa Sacramento Social Club, a boutique Humboldt Park duplex designed for unforgettable gath ...
From $926 per night (USD)VRBO
From $551 per night (USD)VRBO
Historic Humboldt Park Flat Workspace + Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay at Casa Sacramento Gallery House, a boutique Humboldt Park residence blending historic Chicago character with thoug ...
From $551 per night (USD)VRBO
From $236 per night (USD)VRBO
Rooftop, West Loop Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Very spacious unit over a boutique shop. No other tenants in the building with your very own private rooftop d ...
From $236 per night (USD)VRBO
From $268 per night (USD)VRBO
Sunny 3BR - 1Gb Fiber WiFi - EV Charger - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space Bright, modern 3BR/1.5BA home in Chicago—built for remote work and easy stays. Sun-filled, modern decor ...
From $268 per night (USD)VRBO
From $341 per night (USD)VRBO
East Pilsen Palace | Spacious 4BR • Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your modern Chicago retreat, thoughtfully designed for comfortable mid-term stays. This spacious 4-bedroom, 2 ...
From $341 per night (USD)VRBO
From $190 per night (USD)VRBO
Boutique King Room at Hotel Blake Near Millennium Park & Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago's historic Printer's Row neighborhood, Bluegreen Vacations Hotel Blake blends timeless architecture w ...
From $190 per night (USD)VRBO
From $1354 per night (USD)VRBO
Luxury Humboldt Park Home Speakeasy + Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Casa Sacramento Some places offer a beautiful stay. Others offer a story worth becoming part of. Welcome t ...
From $1354 per night (USD)VRBO
From $135 per night (USD)VRBO
Beautiful, furnished condo with great view in luxurious River North high rise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Super host (on another platform) and now looking forward to hosting here on VRBO! This is the perfect home base for you ...
From $135 per night (USD)VRBO
From $244 per night (USD)Expedia
Mid-Century Modern 2 BD APT | Walk to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience stylish comfort in this beautifully designed, mid-century modern apartment in the heart of Wrigleyville. Enjo ...
From $244 per night (USD)Expedia
From $858 per night (USD)VRBO
4BR Apt Same Floor Combo Group Stays Top Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Perfect for your next group trip or corporate offsite, 'The Pop' offers two same-floor apartments for the ulti ...
From $858 per night (USD)VRBO
From $241 per night (USD)VRBO
Edgewater Chic Apt: Near Beach & Eats
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 4 bedrooms, and is ste ...
From $241 per night (USD)VRBO
From $266 per night (USD)VRBO
Beautiful 4 bedroom 2 bath pet friendly Chicago brick bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy your stay at this Chicago style brick bungalow. Well cleaned updated 4 bedroom 2 bath. Near shopping, the universi ...
From $266 per night (USD)VRBO
From $682 per night (USD)Expedia
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this condo. With 3 bedrooms featuring a king, queen, and full bed, this tranquil ...
From $682 per night (USD)Expedia
From $809 per night (USD)VRBO
Luxury Designer Penthouse Combo | NW | Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthous ...
From $809 per night (USD)VRBO
From $537 per night (USD)VRBO
Loyola Lookout – Sporty 3BR Apt Steps from Loyola & Lake w/ Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sporty Style Meets City Comfort – Steps from Loyola, the Lake & the L! Welcome to your home base in Chicago’s vibrant Ro ...
From $537 per night (USD)VRBO