Chicago Rentals
From $632 per night (USD)VRBO
Luxury Suites in Chicago's West Loop – Steps from Dining, Shopping & Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $632 per night (USD)VRBO
From $923 per night (USD)VRBO
Luxury Suites in Chicago's West Loop – Modern Comfort Meets Vibrant City Life
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $923 per night (USD)VRBO
From $453 per night (USD)VRBO
Experience the Suite Life in Chicago’s Iconic Old Town – Spacious Stays Await
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $453 per night (USD)VRBO
From $1690 per night (USD)VRBO
Luxury West Loop Stay: Modern Suites w\/ Balcony, Resort Amenities & City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $1690 per night (USD)VRBO
From $586 per night (USD)VRBO
Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $586 per night (USD)VRBO
From $489 per night (USD)VRBO
Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $489 per night (USD)VRBO
From $700 per night (USD)VRBO
Chic River North Retreat: Luxe Suites, Stunning Views, Steps from Chicago Life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $700 per night (USD)VRBO
From $2853 per night (USD)VRBO
Luxurious Old Town Chicago Suites – Perfect for Families & Corporate Stays
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $2853 per night (USD)VRBO
From $553 per night (USD)VRBO
Historic Charm & Modern Luxury in Chicago’s Iconic Old Town - Stay Level!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $553 per night (USD)VRBO
From $802 per night (USD)VRBO
Experience Chic Chicago Living in Old Town – Spacious Suites & Luxe Amenities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $802 per night (USD)VRBO
From $990 per night (USD)VRBO
Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $990 per night (USD)VRBO
From $270 per night (USD)Expedia
5 Mi to Dtwn: Ukrainian Village Apartment!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Walk to Restaurants | Sleek Furnishings Make the most of your next Windy City adventure when you book this updated Chic ...
From $270 per night (USD)Expedia
From $155 per night (USD)VRBO
Blueground | South Loop, pool & w\/d, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished one bedroom apart ...
From $155 per night (USD)VRBO
From $277 per night (USD)Expedia
House with garage, outdoor dining and basement bar
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this superb house in picturesque Chicago. With 4 queen beds spread across 4 bedrooms and 3 bathrooms equipped ...
From $277 per night (USD)Expedia
From $66 per night (USD)VRBO
Fun relaxing atmosphere home away from home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About this space Enjoy time with friends and family in this fully equipped 2 bedroom, i bath, kitchen and living room a ...
From $66 per night (USD)VRBO
From $83 per night (USD)Expedia
Comfy 2-bedroom apartment with WiFi, in historic Chicago neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your home away from home in Chicago with 2 bedrooms and 1 bathroom. This nice apartment features 1 queen bed, 2 full bed ...
From $83 per night (USD)Expedia
From $464 per night (USD)VRBO
Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $464 per night (USD)VRBO
From $167 per night (USD)Expedia
Cozy 2b2ba: 15 min Bus Downtown, 7min to UChicago, Bike to Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cozy Study: Bronzeville 2b/2ba perfect for remote workers, students, visitors & tourists! Spacious, cozy ...
From $167 per night (USD)Expedia
From $149 per night (USD)VRBO
Blueground | West Loop, gym & bbq, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop Gate. with views over the city. It’ll be easy ...
From $149 per night (USD)VRBO
From $1093 per night (USD)VRBO
Experience Chic Old Town Living: Spacious Suites, Top Amenities & Iconic Locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $1093 per night (USD)VRBO
From $726 per night (USD)VRBO
Luxury West Loop Rentals: Modern Suites w\/ City Views & Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $726 per night (USD)VRBO
From $615 per night (USD)Expedia
Flexhome Ukrainian Village 2BR D2
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Info on listings: - Other listings in this building: flexhome.com/listings/233933 - Minimum stay requirements: if min st ...
From $615 per night (USD)Expedia
From $295 per night (USD)VRBO
Charming 3-bedroom townhome with Central AC and WiFi in lovely Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to this cool townhome in Chicago. This fabulous rental features 3 bedrooms - one with a queen bed and two with t ...
From $295 per night (USD)VRBO
From $339 per night (USD)Expedia
Two Bedroom - Tranquil Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our enchanting 2-bedroom, 1-bathroom haven nestled in the vibrant heart of Wrightwood, Chicago. Ideal for fam ...
From $339 per night (USD)Expedia
From $900 per night (USD)VRBO
Peaceful Oasis - Captivating Six-Bedroom Escape
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Discover the charm of Wrightwood, Chicago, from the comfort of our enchanting 6-bedroom, 3-bathroom rental haven. You wi ...
From $900 per night (USD)VRBO
From $415 per night (USD)Expedia
4BR Home with Game Room: Chicago Leisure Escape
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
This property is managed by @LuxuryLodgingSTR , visit us on the web before booking here for extra savings! ✨Great place ...
From $415 per night (USD)Expedia
From $178 per night (USD)VRBO
Cozy 1 Bedroom Apt near Logan Sq Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This stylish place to stay is perfect for individuals couples or group trips. Kick back and relax in this calm, newly re ...
From $178 per night (USD)VRBO
From $456 per night (USD)Expedia
Andersonville Charming 3 Bedroom\/2 Bath House with Family Room plus Yard & Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED singl ...
From $456 per night (USD)Expedia
From $390 per night (USD)VRBO
3BR Oasis, Gym, Workspace, Quiet Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
✨ The place is really nice she just set it up so all the furniture is brand new and also there's a treadmill and some gy ...
From $390 per night (USD)VRBO
From $556 per night (USD)Expedia
New Modern 3BR, Gym, Workspace, Quiet Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
✨Clean and comfortable space. Accurate description. Safe street. Would love to stay again! ✨ 📢 Welcome to the perfect ...
From $556 per night (USD)Expedia
From $207 per night (USD)VRBO
Charming Chicago 3-bedroom Apartment. Great for Traveling Professionals!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy 2nd floor, three-bedroom apartment awaits, offers comfort and practicality. We are pleased to offer a fully furnish ...
From $207 per night (USD)VRBO
From $504 per night (USD)VRBO
Modern Townhome in the Heart of Hyde Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Located in in the center of Hyde Park, this modern IM Pei townhome is a perfect place for your next stay in Chicago. On ...
From $504 per night (USD)VRBO
From $191 per night (USD)VRBO
Charming 3-bedroom smart house in fabulous Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in Chicago, this delightful smart house offers 3 cozy bedrooms - 2 with queen beds and 1 with a sofa bed. The ba ...
From $191 per night (USD)VRBO
From $588 per night (USD)VRBO
Gracious, spacious vintage home in a terrific neighborhood near the lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A house with real character and color. Filled with art, much by the artist who lives in it. Lots of warm oak floors and ...
From $588 per night (USD)VRBO
From $790 per night (USD)VRBO
South Loop Three Bedroom Two Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Conveniently located near McCormick Place and Soldier Field. Close to parks, shopping, and public transportatio ...
From $790 per night (USD)VRBO
From $936 per night (USD)VRBO
🌟 Modern Humboldt Park 5-Bed, 3.5-Bath Home 🌟
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
✨Light and airy custom built home across from Humboldt Park. Enjoy watching the seasons change around the park and lagoo ...
From $936 per night (USD)VRBO
From $451 per night (USD)VRBO
Updated 3 Bedroom Chicago Downtown Pilsen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Experience Chicago and Pilsen as being in the heart of 18th st. Some of the best food, music and nightlife Chic ...
From $451 per night (USD)VRBO
From $501 per night (USD)VRBO
Chic Chinatown Apt w parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $501 per night (USD)VRBO
From $242 per night (USD)VRBO
COMPLETELY REMODELED, BEAUTIFUL LAKE VIEW FLAT!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Perfect Lake View location for an AirBnB. SHORT walk to Brown/Red line trains, Wrigley Field, Southport Corridor, and a ...
From $242 per night (USD)VRBO
From $668 per night (USD)VRBO
Centrally Located Condo with Parking and Deck!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This condo is located with premier neighborhoods in all four directions. Very easy access to the expressway and subway. ...
From $668 per night (USD)VRBO
From $821 per night (USD)VRBO
Spacious 4BR\/2BA – Private Sun Deck In Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Nestled in the Edgewater neighborhood of Chicago, @TheDreamRentals Skyline Escape is the perfect jumping off po ...
From $821 per night (USD)VRBO
From $108 per night (USD)VRBO
Modern and Stylish Private1BR Garden Apt in Logan Square With Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our cozy and modern West Logan Square garden apartment in one of Chicago's up-and-coming neighborhoods! The ...
From $108 per night (USD)VRBO
From $5294 per night (USD)VRBO
The Lyra: Luxury Group Getaway - Two Penthouses
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 15
Summary: Welcome to The Lyra! 2 penthouses located in the same building and floor. With a primer location in The Loop, r ...
From $5294 per night (USD)VRBO
From $84 per night (USD)VRBO
Cozy 1-bedroom with WiFi and AC in charming Logan Square Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago, this marvelous apartment is a dream. With a cozy bedroom and a comfortable living room featuring a f ...
From $84 per night (USD)VRBO
From $389 per night (USD)VRBO
Stylish & Comfy 2BR\/2.5BTH condo w\/ Pool and Poker table near Med\/United Center
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Experience the charm of this spacious "Game House," minutes from downtown Chicago and the United Center! Perfect for rel ...
From $389 per night (USD)VRBO
From $387 per night (USD)VRBO
Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bedroom apartment. This delightful space features 1 bunk bed and 1 full bed, ...
From $387 per night (USD)VRBO
From $2520 per night (USD)VRBO
Cloud9|Near Millenium Park|The Poppy
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Welcome to The Poppy! 2 apartments located in the same building. To ensure safety, all guests must pass our scr ...
From $2520 per night (USD)VRBO
From $2987 per night (USD)VRBO
Cloud9|5 apartments @Licoln Park|The Walnut
- Bedrooms:
- 10
- Bathrooms:
- 10
- Sleeps:
- 20
Summary: Welcome to The Walnut. 5 Apartments located in the same building. To ensure safety, all guests must pass our sc ...
From $2987 per night (USD)VRBO
From $1913 per night (USD)VRBO
Cloud9 |@TheLoop|Indoor pool|The Pansy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Welcome to The Lotus! 2 apartments located in the same building. To ensure safety, all guests must pass our scr ...
From $1913 per night (USD)VRBO
From $3609 per night (USD)VRBO
Cloud9|6 apartments @Licoln Park|The Willow
- Bedrooms:
- 12
- Bathrooms:
- 12
- Sleeps:
- 24
Summary: Welcome to The Willow. 6 Apartments located in the same building. To ensure safety, all guests must pass our sc ...
From $3609 per night (USD)VRBO
From $2358 per night (USD)VRBO
Cloud9|4 Apartments @LincolnPark|The Cedar
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: Welcome to The Cedar. 4 Apartments located in the same building. To ensure safety, all guests must pass our scr ...
From $2358 per night (USD)VRBO
From $1572 per night (USD)VRBO
Cloud9|Golf,Gym,CoWorking@LincolnPark|The Ash
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to The Ash, 2 Apartments located in the same building. To ensure safety, all guests must pass our scree ...
From $1572 per night (USD)VRBO
From $173 per night (USD)VRBO
Chic 2-Bedroom\/1 Bath Apartment in Fully Renovated Rowhouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Chicago is waiting for you at this lovely 2-bedroom apartment. This delightful space offers all the comforts you need, f ...
From $173 per night (USD)VRBO
From $994 per night (USD)VRBO
Luxury Two-Level Townhouse | Patio | Lincoln Park
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: NEWLY RENOVATED TOWNHOUSE IN THE HEART OF LINCOLN PARK! This private luxury townhouse (duplex) is perfectly lo ...
From $994 per night (USD)VRBO
From $210 per night (USD)VRBO
Charming 2-bedroom 1 bathroom with plunge pool, new gazebo @ Bridgeport Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes new gazebo, ...
From $210 per night (USD)VRBO
From $452 per night (USD)Expedia
Chic Modern NEW Loft near United Center, UIC\/IMD & Downtown W\/ Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Discover luxury in our newly renovated 2nd floor loft in Tri-Taylor. With 13-ft ceilings, large windows, brick and moder ...
From $452 per night (USD)Expedia
From $327 per night (USD)VRBO
Spacious, one-level condo next to Jackson Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...
From $327 per night (USD)VRBO
From $394 per night (USD)VRBO
Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and ...
From $394 per night (USD)VRBO
From $429 per night (USD)VRBO
Cozy Chinatown Apartment w free parking spot!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $429 per night (USD)VRBO
From $380 per night (USD)VRBO
Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This styl ...
From $380 per night (USD)VRBO
From $75 per night (USD)VRBO
Historic Worker's Cottage with Vintage Charm Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Cozy and serene, this restored 1880s worker's cottage is the perfect place to explore Chicago. You'll have the entire ho ...
From $75 per night (USD)VRBO
From $775 per night (USD)VRBO
Wrigleyville Garden 1BR
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $775 per night (USD)VRBO
From $2601 per night (USD)VRBO
Luxury Designer Penthouse Combo |North| 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 penthouses ...
From $2601 per night (USD)VRBO
From $385 per night (USD)VRBO
Charming Chicago Apt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Discover comfort and convenience in this spacious two-bedroom, two-bath apartment, ideally designed to accommod ...
From $385 per night (USD)VRBO
From $1665 per night (USD)VRBO
Wrigleyville 3BD Condo
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1665 per night (USD)VRBO
From $1570 per night (USD)VRBO
Wrigleyville Garden 3BR\/9beds Pod
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1570 per night (USD)VRBO
From $3382 per night (USD)VRBO
Six-Bedrooms in Wrigleyville
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 16
Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...
From $3382 per night (USD)VRBO
From $1686 per night (USD)VRBO
Luxury Designer Penthouse Combo |South| Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1686 per night (USD)VRBO
From $231 per night (USD)VRBO
3 Bedroomin the Medical Center!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: A couple houses off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Fu ...
From $231 per night (USD)VRBO
From $494 per night (USD)VRBO
South Loop 4 Bedroom apt
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Summary: South Loop 4 bedroom apartment with 1.5 bathrooms. We are centrally located and very easy to get anywhere in th ...
From $494 per night (USD)VRBO
From $887 per night (USD)VRBO
Chicago Mid-Century Gem By United Center
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 18
Summary: Welcome to the Chicago Mid-Century Gem, an extraordinary urban retreat located mere steps from the renowned Uni ...
From $887 per night (USD)VRBO
From $790 per night (USD)VRBO
Chic 2BR 2BA Condo with Balcony - River North Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to our chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Per ...
From $790 per night (USD)VRBO
From $360 per night (USD)VRBO
Quick Drive to Downtown Chicago & Early Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Book your perfect Chicago getaway at this spacious condo, just minutes from downtown and the United Center! Ideal for gr ...
From $360 per night (USD)VRBO
From $79 per night (USD)VRBO
Musician's Quarters\n\nChicago Jazz , Season discount
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Host Chester of Musicians Quarters is offering a Super Cheap BACK TO SCHOOL OFFER. $79 PER NIGHT. From August 21st to Au ...
From $79 per night (USD)VRBO
From $1064 per night (USD)VRBO
Luxury Designer Penthouse West |Pool| Gold Coast
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...
From $1064 per night (USD)VRBO
From $1080 per night (USD)Expedia
Top 1 Rated 4BR Lincoln Park House - King Bed
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
🌟 This property is managed by @LuxuryLodgingSTR , visit us on the web before booking here for extra savings! 🌟 ✨ I hi ...
From $1080 per night (USD)Expedia
From $1090 per night (USD)VRBO
Luxury Loft Collection 703 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...
From $1090 per night (USD)VRBO
From $447 per night (USD)VRBO
Stylish 2BR Urban Retreat in River West
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Welcome to our contemporary 2-bedroom, 1-bathroom condo in lively River West. Ideal for business and leisure, t ...
From $447 per night (USD)VRBO
From $583 per night (USD)VRBO
Stay Inn South Shore- Pool Table, Arcade, Sleeps 10, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our stylish South Shore retreat, perfect for families and special events. This spacious 4-bedroom, 3-bathroom ...
From $583 per night (USD)VRBO
From $401 per night (USD)VRBO
Updated 3 Bedroom Chicago Historic Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $401 per night (USD)VRBO
From $448 per night (USD)VRBO
Pulaski Mahal - Spacious “Smart” Home with Game Room. Close to Hwy, train, EL.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $448 per night (USD)VRBO
From $381 per night (USD)VRBO
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...
From $381 per night (USD)VRBO
From $244 per night (USD)VRBO
2BD\/1 BA with summer patio in quiet Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $244 per night (USD)VRBO
From $249 per night (USD)Expedia
Wrigleyville Suites Room 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $249 per night (USD)Expedia
From $381 per night (USD)VRBO
❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Chicago! Whether you’re in town to seal a business deal or have a short holiday breather, our warm three-bed ...
From $381 per night (USD)VRBO
From $183 per night (USD)VRBO
Bright 3BR\/1BA FREE Parking\/Laundry in Pilsen. Minutes from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Escape to the vibrant heart of Pilsen and experience Chicago like a local in our charming home: -Fully equipped, modern ...
From $183 per night (USD)VRBO
From $192 per night (USD)VRBO
Perfect 2BD\/1BA FREE Garage Parking\/Laundry in Pilsen. Minutes to downtown.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover our 2-bed, 1-bath Pilsen gem! Adorned with local art, a workspace, and free parking & laundry, it's minutes fro ...
From $192 per night (USD)VRBO
From $880 per night (USD)VRBO
Chic River North Condo 2BR 2BA with Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our riverfront oasis nestled in the vibrant heart of Chicago's trendy River North neighborhood! Thi ...
From $880 per night (USD)VRBO
From $322 per night (USD)VRBO
A Home Away From Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the allure of this newly renovated Georgian house. Boasting ample space for family enjoyment. With its close pr ...
From $322 per night (USD)VRBO
From $582 per night (USD)VRBO
River North Central Home With Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Enjoy a stylish experience at @TheDreamRentals centrally-located home in Chicago's River West neighborhood. Rel ...
From $582 per night (USD)VRBO
From $335 per night (USD)VRBO
Fulton market \/ Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...
From $335 per night (USD)VRBO
From $419 per night (USD)VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...
From $419 per night (USD)VRBO
From $270 per night (USD)VRBO
Chicago Rental - Vernon Ave
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
2600 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 5 bedrooms ...
From $270 per night (USD)VRBO
From $223 per night (USD)Expedia
Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...
From $223 per night (USD)Expedia
From $960 per night (USD)VRBO
The Grand Kimball Lodge, Logan Square, Sleeps 14
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: Welcome to The Grand Kimball Lodge, a truly unique getaway featured in Architectural Digest's "21 Best Chicago ...
From $960 per night (USD)VRBO
From $137 per night (USD)VRBO
Stunning Suite 2 @ Hotel Nemo Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...
From $137 per night (USD)VRBO
Click For PricingVRBO
Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
Click For PricingVRBO
From $218 per night (USD)Expedia
Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lake View East. with balcony views over the city. It’ll ...
From $218 per night (USD)Expedia
From $126 per night (USD)VRBO
Dreamy Streeterville Studio w\/ Pool & Gym, nr Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Streeterville. with high floor views over the city. It’ ...
From $126 per night (USD)VRBO
From $126 per night (USD)Expedia
Deluxe Loop 1BR w\/ Gym & Doorman, nr L & Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $126 per night (USD)Expedia