Chicago Harbor Rentals
From $95 per night (USD)VRBO
Blueground | Gold Coast, rooftop & gym, nr Hancock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Streeterville. It’ll be easy to simply show up and start liv ...
From $95 per night (USD)VRBO
From $112 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 be ...
From $112 per night (USD)Expedia
From $202 per night (USD)VRBO
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 $202 per night (USD)VRBO
From $238 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 be ...
From $238 per night (USD)Expedia
From $131 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 $131 per night (USD)VRBO
From $277 per night (USD)Expedia
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 $277 per night (USD)Expedia
From $616 per night (USD)VRBO
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $616 per night (USD)VRBO
From $907 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 $907 per night (USD)VRBO
From $370 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 $370 per night (USD)VRBO
From $370 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 $370 per night (USD)VRBO
From $486 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 $486 per night (USD)VRBO
From $2557 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 $2557 per night (USD)VRBO
From $435 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 $435 per night (USD)VRBO
From $654 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 $654 per night (USD)VRBO
From $112 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 $112 per night (USD)VRBO
From $109 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 $109 per night (USD)Expedia
From $1409 per night (USD)VRBO
Luxury Designer Combo | Private Patio | Gold Coast
- Bedrooms:
- 6
- Bathrooms:
- 6
- 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 $1409 per night (USD)VRBO
From $250 per night (USD)Expedia
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 $250 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 $176 per night (USD)Expedia
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 $176 per night (USD)Expedia
From $120 per night (USD)VRBO
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 $120 per night (USD)VRBO
From $2611 per night (USD)Expedia
Modern- Smart Home in Wicker Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy and relax in this calm, modern, stylish space located in Wicker Park. This plant filled oasis in the city i ...
From $2611 per night (USD)Expedia
From $540 per night (USD)VRBO
Best Place to Unwind! 2 Family and Dog Friendly Units! Walk to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $540 per night (USD)VRBO
From $708 per night (USD)VRBO
Relax & Explore! 3 King Units, Steps from Riverfront, Pet-Friendly Property!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $708 per night (USD)VRBO
From $1080 per night (USD)VRBO
Four Cozy Queen Rooms! Perfect for Family & Friends, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $1080 per night (USD)VRBO
From $810 per night (USD)VRBO
3 Comfortable Units! Pet-friendly Property! Near Riverwalk & Chicago Attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $810 per night (USD)VRBO
From $472 per night (USD)VRBO
Look No Further! 2 Stylish King Units! Pet-Friendly, Walk to Riverwalk & Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $472 per night (USD)VRBO
From $1410 per night (USD)VRBO
Great Relaxing Overnight Stay! 4 Units with City View, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1410 per night (USD)VRBO
From $69 per night (USD)VRBO
The Chicago Hotel Collection, Standard Double Queen with City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $69 per night (USD)VRBO
From $618 per night (USD)Expedia
Luxury Designer Penthouse NW | Pool | Gold Coast
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $618 per night (USD)Expedia
From $1505 per night (USD)VRBO
Making The Best Memories Along The Way! 4 Units with City View, Pets Are Welcome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1505 per night (USD)VRBO
From $753 per night (USD)VRBO
Better Choice for your Vacation! 2 Relaxing Units with City View, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $753 per night (USD)VRBO
From $1129 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Relaxing Units, Pets Are Welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1129 per night (USD)VRBO
From $711 per night (USD)VRBO
A Place You'll Surely Enjoy! 2 Relaxing Units with City View, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $711 per night (USD)VRBO
From $1066 per night (USD)VRBO
Come Create Memories w/ Fun-filled Adventures at this Paradise! 3 Relaxing Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1066 per night (USD)VRBO
From $202 per night (USD)VRBO
Better Choice for your Vacation! Short Walk to River North Spots, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $202 per night (USD)VRBO
From $209 per night (USD)VRBO
Everything You Need For The Perfect Vacation! Pet-friendly Property, King Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $209 per night (USD)VRBO
From $87 per night (USD)Expedia
Blueground | Gold Coast, AC, nr Hancock Center
- 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 $87 per night (USD)Expedia
From $372 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $372 per night (USD)VRBO
From $207 per night (USD)VRBO
Sleek Downtown Retreat by Chicago’s Mag Mile @ The Chicago Hotel Collection
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $207 per night (USD)VRBO
From $134 per night (USD)VRBO
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $134 per night (USD)VRBO
From $69 per night (USD)VRBO
Upscale City Center Stay | Prime Locale | City Views | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $69 per night (USD)VRBO
From $320 per night (USD)VRBO
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy South Loop furnished one bedroom apartme ...
From $320 per night (USD)VRBO
From $327 per night (USD)Expedia
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $327 per night (USD)Expedia
From $228 per night (USD)VRBO
Suite Success • Business Class Living • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your extended-stay retreat in the heart of Chicago’s South Loop. Whether you’re here for work, relocating to ...
From $228 per night (USD)VRBO
From $283 per night (USD)Expedia
Penthouse Paradise •Executive Elegance • Elevated Amenities • Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Elevated Urban Luxury in Chicago’s South Loop: Welcome to your home away from home—a sprawling, sun-drenched ...
From $283 per night (USD)Expedia
From $129 per night (USD)VRBO
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $129 per night (USD)VRBO
From $128 per night (USD)Expedia
Free Coffee & Private Room - Traveler's Favorite!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $128 per night (USD)Expedia
From $126 per night (USD)VRBO
Traveler’s Favorite: Private Room Near Attractions
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $126 per night (USD)VRBO
From $128 per night (USD)Expedia
Clean & Modern • Central Location • Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $128 per night (USD)Expedia
From $131 per night (USD)VRBO
Secure, Quiet, Solo Traveler's Fave, Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $131 per night (USD)VRBO
From $128 per night (USD)Expedia
Morning Brew & Museum Views • Downtown Solo Stay
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $128 per night (USD)Expedia
From $131 per night (USD)VRBO
Best Private Room in Downtown | Free Coffee
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $131 per night (USD)VRBO
From $128 per night (USD)Expedia
Budget-Friendly Stay and Free Coffee | Downtown
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $128 per night (USD)Expedia
From $129 per night (USD)VRBO
All Ease Private Stay |Traveler's Top Fave!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $129 per night (USD)VRBO
From $126 per night (USD)Expedia
Solo Explorer’s Nest | Walk to Museums & Parks
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $126 per night (USD)Expedia
From $127 per night (USD)VRBO
Best Pick | Private Room w/ Free Coffee and WiFi
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $127 per night (USD)VRBO
From $128 per night (USD)Expedia
Secure, Private, Free Wi-Fi and Coffee, Accessible
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $128 per night (USD)Expedia
From $132 per night (USD)VRBO
Work, Explore, Rest | Ideal for Solo Guests
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $132 per night (USD)VRBO
From $176 per night (USD)Expedia
Private Stay w/Free Coffee | Best Stay in Chicago
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $176 per night (USD)Expedia
From $90 per night (USD)VRBO
Blueground | Rush & Division, fitness center, nr Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $90 per night (USD)VRBO
From $489 per night (USD)Expedia
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $489 per night (USD)Expedia
From $231 per night (USD)VRBO
Cozy Room with Rooftop Lounge & City Views in River North
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 355 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $231 per night (USD)VRBO
From $559 per night (USD)Expedia
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $559 per night (USD)Expedia
From $200 per night (USD)VRBO
Luxury Unit with Rooftop Lounge & Spectacular City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 248 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $200 per night (USD)VRBO
From $276 per night (USD)Expedia
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 301 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $276 per night (USD)Expedia
From $466 per night (USD)VRBO
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $466 per night (USD)VRBO
From $391 per night (USD)Expedia
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $391 per night (USD)Expedia
From $243 per night (USD)VRBO
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 355 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $243 per night (USD)VRBO
From $1134 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 2 Modern Units, Pets are Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $1134 per night (USD)VRBO
From $286 per night (USD)VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $286 per night (USD)VRBO
From $599 per night (USD)VRBO
Spacious Good-Value Accommodation! Pet-Friendly Property, Near Willis Tower!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $599 per night (USD)VRBO
From $595 per night (USD)VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $595 per night (USD)VRBO
From $369 per night (USD)VRBO
Affordability Meets Comfort! Close to Water Tower Chicago, Pets Are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $369 per night (USD)VRBO
From $311 per night (USD)VRBO
Always a Great Idea To Unwind! Pet-Friendly Property, Near Marina City!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $311 per night (USD)VRBO
From $285 per night (USD)VRBO
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $285 per night (USD)VRBO
From $152 per night (USD)VRBO
Upscale River North 1BR w/ Coffee Shop & Gym, nr Lake, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North with views over the city. It’ll be easy to s ...
From $152 per night (USD)VRBO
From $273 per night (USD)Expedia
Stylish Streeterville 2BR w/ Lounge & Pool, nr Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $273 per night (USD)Expedia
From $148 per night (USD)VRBO
Great South Loop 1BR w/ Games & Pool, nr Park & Train, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. It’ll be easy to simply show up and start l ...
From $148 per night (USD)VRBO
Click For PricingExpedia
Upscale Streeterville Jr 1BR w/ Gym, nr Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
Click For PricingExpedia
From $226 per night (USD)VRBO
Trendy Loop Jr 1BR w/ Game Room, nr Park & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Chicago Loop furnished one bedroom apa ...
From $226 per night (USD)VRBO
From $131 per night (USD)Expedia
Stellar South Loop 1BR, near CTA Train, Sports & Parks, by blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $131 per night (USD)Expedia
From $90 per night (USD)VRBO
Striking South Loop 1BR w/ Rooftop, walk to Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...
From $90 per night (USD)VRBO
From $85 per night (USD)Expedia
Sweet South Loop 1BR w/ Rooftop, nr Grant Park & Museums, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...
From $85 per night (USD)Expedia
From $118 per night (USD)VRBO
Sunny South Loop 1BR, nr Soldier Field, CTA Train & Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. It’ll be easy to simply show up and start l ...
From $118 per night (USD)VRBO
From $766 per night (USD)Expedia
Luxury Loft Collection 903 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $766 per night (USD)Expedia
From $758 per night (USD)VRBO
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $758 per night (USD)VRBO
From $331 per night (USD)Expedia
Gold Coast/Downtown Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New Listing! Freshly renovated Gold Coast hideaway provides the perfect escape from the nearby shopping and restaurant a ...
From $331 per night (USD)Expedia
From $271 per night (USD)VRBO
Chicago Cityview Chic II Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...
From $271 per night (USD)VRBO
From $1381 per night (USD)Expedia
Downtown Penthouse 5bd VIEWS|Parking, Gym+Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with M ...
From $1381 per night (USD)Expedia
From $1085 per night (USD)VRBO
2 Connecting Suites at a 4⭐️ Hotel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Delight in exclusive access to the Club Lounge in the Executive Suite at the Renaissance Chicago Downtown Hotel. This 80 ...
From $1085 per night (USD)VRBO
From $569 per night (USD)VRBO
Discover Downtown from Our Well-Appointed Space | 2 Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Downtown at Your Doorstep: In the vibrant Loop's heart, our boutique hotel is an urban oasis. Near the Art Institute & M ...
From $569 per night (USD)VRBO
From $345 per night (USD)VRBO
Downtown 2bd #4 - Near Grant Park, Museums, Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $345 per night (USD)VRBO
From $2274 per night (USD)Expedia
Luxury Downtown PH: Bean & Lake Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Chicago's Exclusive Orion Penthouse! Wake to breathtaking Bean & Park views from your 21st-floor, 3000ft² haven ...
From $2274 per night (USD)Expedia
From $89 per night (USD)VRBO
Blueground | South Loop 1bd apartment
- 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 $89 per night (USD)VRBO
From $5136 per night (USD)VRBO
The Lyra: Luxury Group Getaway - Two Penthouses
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
Summary: Discover 'The Lyra', a collection of two exclusive penthouses on the same floor in The Loop, perfectly situated ...
From $5136 per night (USD)VRBO
From $320 per night (USD)VRBO
South Loop 4 Bedroom apt
- Bedrooms:
- 1
- Bathrooms:
- 4
- 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 $320 per night (USD)VRBO
From $1415 per night (USD)VRBO
Luxury Designer Penthouse Combo |South| 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 $1415 per night (USD)VRBO
From $1532 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 $1532 per night (USD)VRBO
From $755 per night (USD)Expedia
Luxury Loft Collection 703 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...
From $755 per night (USD)Expedia