Chicago Rentals
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 $432 per night (USD)Expedia
Chicago West Town Row House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Located in Chicago’s West Town neighborhood, you, your family and friends will be close to everything when you stay at t ...
From $432 per night (USD)Expedia
From $195 per night (USD)VRBO
Charming Home in Portage Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This cozy four-bedroom, two-bathroom home is ideally located near O’Hare Airport and downtown Chicago, offering convenie ...
From $195 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 $431 per night (USD)VRBO
Charming 4-bedroom house with WiFi, AC in superb Chicago Chatham
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this charming house in Chicago, centrally located and perfect for small groups or families. This marvelous p ...
From $431 per night (USD)VRBO
From $117 per night (USD)Expedia
Comfortable 2-bedroom apartment in phenomenal Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home! Comfortable apartment with an open layout, modern kitchen, and stainless steel appl ...
From $117 per night (USD)Expedia
Click For PricingVRBO
Charming 2-bedroom condo with AC and WiFi in lakefront downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Chicago at this charming condo. With 2 bedrooms featuring 2 queen beds, 2 bathrooms with a shower with body so ...
Click For PricingVRBO
From $55 per night (USD)Expedia
Twin bed room , smart TV 32\" with shared bathroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This quaint bungalow in Chicago is perfect for your solo retreat. Bedroom With a cozy featuring a twin bed, Smart tv 32 ...
From $55 per night (USD)Expedia
From $170 per night (USD)VRBO
Charming 3-bedroom apartment in the Old Norwood Park neighborhood of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Discover this captivating 3-bedroom apartment nestled within a historic building in the heart of Old Norwood Park. This ...
From $170 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 $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 $139 per night (USD)VRBO
Blueground | River North, pool & w\/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $139 per night (USD)VRBO
From $182 per night (USD)Expedia
Blueground | The Loop, pool & w\/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $182 per night (USD)Expedia
From $2093 per night (USD)VRBO
Luxury Designer Combo | Private Patio | Gold Coast
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 20
Summary: TWO BRAND NEW APARTMENTs IN THE HEART OF GOLD COAST! Enjoy your own luxury units in Chicago's Gold Coast-the c ...
From $2093 per night (USD)VRBO
From $168 per night (USD)Expedia
Blueground | River North, pool & w\/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in River North. with balcony views over the city. It’ll be ...
From $168 per night (USD)Expedia
From $153 per night (USD)VRBO
Blueground | The Loop, pool & w\/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop. with high floor views over the city. It’l ...
From $153 per night (USD)VRBO
From $159 per night (USD)Expedia
Blueground | River North, pool & AC, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $159 per night (USD)Expedia
From $158 per night (USD)VRBO
Blueground | Streeterville, pool & gym, nr pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this beautiful one bedroom Blueground apartment. You’ll love comin ...
From $158 per night (USD)VRBO
From $298 per night (USD)Expedia
Spacious 4-bedroom house in awesome Chicago with WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Chicago is waiting for you at this 4-bedroom house. With 1 king bed, 1 full bed, and 1 child bed, this lovely property o ...
From $298 per night (USD)Expedia
From $186 per night (USD)VRBO
Blueground | River North, pool & w\/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $186 per night (USD)VRBO
From $181 per night (USD)Expedia
Blueground | River North, pool & w\/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in River North. with balcony views over the city. It’ll be ...
From $181 per night (USD)Expedia
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
Click For PricingExpedia
Blueground | Hyde Park, AC, w\/d, nr museum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in East Hyde Park. with views over the city. It’ll be easy ...
Click For PricingExpedia
From $117 per night (USD)VRBO
Blueground | The Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop. with high floor views over the city. It’l ...
From $117 per night (USD)VRBO
From $144 per night (USD)Expedia
Blueground | The Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Chicago Loop furnished one bedroom apart ...
From $144 per night (USD)Expedia
From $164 per night (USD)VRBO
Charming 3-bedroom house with AC and WiFi in phenomenal Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Make yourself at home in this 3-bedroom Chicago retreat. This house boasts 1 queen bed and 2 full beds, perfect for a gr ...
From $164 per night (USD)VRBO
From $232 per night (USD)Expedia
Welcome to Lux! 2BR in Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a stylish experience at this centrally-located place. This 1,100 square foot apartment offers comfortable and comp ...
From $232 per night (USD)Expedia
From $516 per night (USD)VRBO
NEW! Charming Belmont Heights Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover your home away from home in this newly renovated 4-bedroom, 2-bathroom single-family gem in the serene Belmont ...
From $516 per night (USD)VRBO
From $1975 per night (USD)Expedia
Chicago Gold Coast Luxury Penthouse Rooftop Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in unmatched luxury at this stunning 4-bedroom penthouse in Chicago’s iconic Gold Coast neighborhood. Perfectly ...
From $1975 per night (USD)Expedia
From $106 per night (USD)VRBO
Chic 1-bedroom apartment in amazing Chicago location with Gigabit-WiFi & AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Make yourself at home in this welcoming 1-bedroom Chicago retreat. This apartment features a cozy living room with a sof ...
From $106 per night (USD)VRBO
From $297 per night (USD)VRBO
Modern & Spacious Stay in Historic Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Welcome to this spacious 3-bedroom, 2-bathroom apartment in the heart of Bronzeville! Perfect for families, fri ...
From $297 per night (USD)VRBO
From $148 per night (USD)VRBO
Blueground | Lakeshore East, pool & w\/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in New Eastside. with balcony views over the city. It’ll b ...
From $148 per night (USD)VRBO
From $201 per night (USD)Expedia
Blueground | Lakeshore East, pool & w\/d, nr park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $201 per night (USD)Expedia
From $712 per night (USD)VRBO
Modern 2-bedroom townhome in Chicago with private patio
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to the safe and peaceful Chicago neighborhood Bucktown! This property lives like a single family home and consis ...
From $712 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 $348 per night (USD)VRBO
Spacious 3-bedroom apartment in cool Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 4-bedroom Chicago retreat. This marvelous apartment features 4 queen beds, a cozy living s ...
From $348 per night (USD)VRBO
From $613 per night (USD)Expedia
LUXE Vintage Green Loft - 10min to Downtown, Movie Rm, Student & Family-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to a Luxury Vintage Getaway with a 24/7 dedicated team ensuring a comfortable and unforgettable stay. ✔ Central ...
From $613 per night (USD)Expedia
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 $178 per night (USD)Expedia
Blueground | Lakeshore East, pool & w\/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in New Eastside. with balcony views over the city. It’ll b ...
From $178 per night (USD)Expedia
From $144 per night (USD)VRBO
Blueground | Lakeshore East, pool & w\/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $144 per night (USD)VRBO
From $356 per night (USD)Expedia
Modern Ukrainian Village Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your stylish retreat in Chicago’s vibrant Ukrainian Village! This newly renovated, modern condo offers two sp ...
From $356 per night (USD)Expedia
From $214 per night (USD)VRBO
River North High Rise w\/Amazing Views and Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
31+ day rental ONLY. Fully furnished and all utilities included. Amazing views of the city from this oasis perched in th ...
From $214 per night (USD)VRBO
From $132 per night (USD)Expedia
Blueground | West Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable West Loop Gate furnished one bedr ...
From $132 per night (USD)Expedia
From $225 per night (USD)VRBO
Blueground | River North, rooftop & gym, nr Mart
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish River North furnished one bedroom apa ...
From $225 per night (USD)VRBO
From $210 per night (USD)Expedia
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your new home away from home! This beautiful townhouse offers a cozy retreat with a queen bed and a full bed. Enjoy the ...
From $210 per night (USD)Expedia
From $463 per night (USD)VRBO
Spacious 4-bedroom apartment in fabulous Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This Chicago apartment boasts 4 inviting bedrooms with queen beds. The bathroom comes equipped with a bathtub and a hair ...
From $463 per night (USD)VRBO
From $326 per night (USD)Expedia
Spacious 4-bedroom duplex in Wicker Park\/Humboldt Park with 1 Parking spot
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your cozy getaway awaits in Chicago at this charming duplex apartment with 20 ft high ceilings. With 4 bedrooms includin ...
From $326 per night (USD)Expedia
From $167 per night (USD)VRBO
Spacious 4-bedroom house in cool Chicago with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful 4 bedroom lots of closets / 2 bath home Central A/C * Huge 'Chef' Kitchen with stove, microwave, fridge, dish ...
From $167 per night (USD)VRBO
From $327 per night (USD)Expedia
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $327 per night (USD)Expedia
From $49 per night (USD)VRBO
1-bedroom apartment - 1200 per Month- 20% Discount 1st month\nUtllities Included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Make yourself at home in this delightful 1-bedroom Chicago retreat. The cozy apartment features a comfortable queen bed, ...
From $49 per night (USD)VRBO
From $103 per night (USD)Expedia
< 2 Mi to UChicago: Apt Near Bus Stops!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Laptop-Friendly Desk | 3 Smart TVs | 7 Mi to The Loop Nestled in the Washington Park neighborhood, this Chicago vacati ...
From $103 per night (USD)Expedia
From $279 per night (USD)VRBO
Andersonville Charming 3 Bedroom\/2 Bath House with Family Room plus Yard & Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED sing ...
From $279 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 $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 $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)VRBO
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)VRBO
From $149 per night (USD)Expedia
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)Expedia
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 $144 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. . It’ll be easy to simply show up and start ...
From $144 per night (USD)VRBO
From $263 per night (USD)Expedia
Chic 2-bedroom apartment with WiFi, AC in lovely Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay comfortably in Chicago at this 2-bedroom apartment. This charming property features 1 king bed and 1 queen bed, per ...
From $263 per night (USD)Expedia
From $527 per night (USD)VRBO
Luxury Meets Comfort: River North Rentals with Chic Style & Prime Chicago Access
- 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 $527 per night (USD)VRBO
From $446 per night (USD)VRBO
Stay Chic in Chicago: River North Suites w\/ Luxe Amenities & Prime Location!
- 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 $446 per night (USD)VRBO
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 $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 $295 per night (USD)Expedia
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)Expedia
From $339 per night (USD)VRBO
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)VRBO
From $900 per night (USD)Expedia
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)Expedia
From $415 per night (USD)VRBO
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)VRBO
From $178 per night (USD)Expedia
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)Expedia
From $456 per night (USD)VRBO
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)VRBO
From $390 per night (USD)Expedia
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)Expedia
From $556 per night (USD)VRBO
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)VRBO
From $207 per night (USD)Expedia
Charming Chicago 3-bedroom Apartment. Extend Stay Discount
- 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)Expedia
From $302 per night (USD)VRBO
Quiet 3-bedroom house in amazing Chicago with WiFi & AC. Near Everything!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house in Chicago is perfect for your escape to the Windy City. With 3 queen beds, 1.5 bathrooms featuring ...
From $302 per night (USD)VRBO
From $234 per night (USD)VRBO
Central 1BR Retreat – Cozy & Inviting Near Loyola
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover a cozy 1BR/1BA just steps from Loyola University and Lake Michigan! This charming unit offers a blend of comfor ...
From $234 per night (USD)VRBO
From $292 per night (USD)VRBO
Chic 2BR Getaway Queen Beds Fast WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home! This comfy apartment offers an inviting and cozy atmosphere, making it the perfect ...
From $292 per night (USD)VRBO
From $161 per night (USD)Expedia
Charming 2-bedroom apartment in enchanting Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this 2-bedroom Chicago retreat. This excellent apartment features 2 queen beds, a cozy living r ...
From $161 per night (USD)Expedia
From $475 per night (USD)VRBO
Prime Location! 3BRGem near University of Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our home is located in the desirable Southside neighborhood of Chicago. The area is known for its vibrant culture, diver ...
From $475 per night (USD)VRBO
From $271 per night (USD)VRBO
Cozy Retreat, Prime Location Near Loyola & Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy the ideal mix of comfort and convenience in this cozy 1BR/1BA Airbnb, just steps from Loyola University and Lake M ...
From $271 per night (USD)VRBO
From $230 per night (USD)VRBO
Prime location in Lakeview Near Wrigleyville With Washer & Dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this fabulous 2-bedroom gem in Chicago. This adorable apartment features a cozy queen bed, two charming twin be ...
From $230 per night (USD)VRBO
From $329 per night (USD)Expedia
Prime Location: Cozy 1BR Near Dining & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in this comfortable 1-bedroom apartment, designed for relaxation and convenience. Sleep soundly on the queen-size ...
From $329 per night (USD)Expedia
From $356 per night (USD)VRBO
Central Haven Escape: Stylish 3BR With Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Unwind in our cozy and modern 3-bedroom retreat, perfect for relaxing after exploring the city. Two bedrooms feature plu ...
From $356 per night (USD)VRBO
From $183 per night (USD)Expedia
Be our guest in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this fabulous 2-bedroom gem in Chicago. This soothing apartment features 1 king bed and 1 queen bed, a cozy bat ...
From $183 per night (USD)Expedia