Crown Fountain Rentals
From $197 per night (USD)VRBO
Cozy Room w/ Historic Charm & Modern Amenities in Heart of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)VRBO
From $208 per night (USD)VRBO
Elegant Room w/ Modern Conveniences & Walkable to Major Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)VRBO
From $208 per night (USD)VRBO
Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)VRBO
From $185 per night (USD)Expedia
Professionally Managed 1 Bedroom in the Chicago Loop by the Theater District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago, enjoy what this 1-bedroom apartment has to offer. This superb space features a welcoming queen bed, ...
From $185 per night (USD)Expedia
From $96 per night (USD)VRBO
Blueground | Streeterville, pool & gym, nr pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $96 per night (USD)VRBO
From $104 per night (USD)Expedia
Blueground | River North, balcony & pool, nr Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...
From $104 per night (USD)Expedia
From $439 per night (USD)VRBO
3 Tranquil Eco-friendly Rooms, Fitness Center, Near River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $439 per night (USD)VRBO
From $163 per night (USD)VRBO
Experience Comfort in Eco-friendly Room w/ Earth Tone Furniture
- 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 $163 per night (USD)VRBO
From $150 per night (USD)VRBO
Relaxing Eco-friendly Room w/ Modern Decor near River North Attractions
- 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 $150 per night (USD)VRBO
From $150 per night (USD)VRBO
Cozy Eco-friendly Room w/ Earth Tone Decor, Short Walk to River North Spots
- 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 $150 per night (USD)VRBO
From $1679 per night (USD)VRBO
Luxury Penthouse: Iconic Views + Exclusive Comfort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Discover a premier Chicago experience in this luxury penthouse, ideal for travelers who value amazing views and ...
From $1679 per night (USD)VRBO
From $203 per night (USD)Expedia
Blueground | The 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 roomy Chicago Loop furnished one bedroom apar ...
From $203 per night (USD)Expedia
From $223 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 $223 per night (USD)VRBO
From $146 per night (USD)Expedia
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 $146 per night (USD)Expedia
From $149 per night (USD)VRBO
Blueground | Streeterville, pool & gym, nr Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with views over the city. It’ll be easy t ...
From $149 per night (USD)VRBO
From $469 per night (USD)Expedia
53-54 Floor Penthouse
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Penthouses at Grand Plaza PH#B This stunning two-story Penthouse soars above Chicago, featuring dramatic li ...
From $469 per night (USD)Expedia
From $364 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 $364 per night (USD)VRBO
From $403 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 $403 per night (USD)VRBO
From $297 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 $297 per night (USD)VRBO
From $504 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 $504 per night (USD)VRBO
From $723 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 $723 per night (USD)VRBO
From $249 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile Upscale Saint Clair Suite, 3 Units
- 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 $249 per night (USD)VRBO
Click For PricingVRBO
Blueground | River North, pool & AC, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North furnished one bedroom apa ...
Click For PricingVRBO
From $106 per night (USD)Expedia
Blueground | The Loop, elevator, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Chicago Loop furnished one bedroom ap ...
From $106 per night (USD)Expedia
From $560 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 fa ...
From $560 per night (USD)VRBO
From $337 per night (USD)VRBO
The Ultimate Chicago Experience! Close to Chicago Riverwalk and Picasso Statue
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $337 per night (USD)VRBO
From $380 per night (USD)VRBO
Ideal Mix of Comfort and Value! 2 Comfortable Units, Near Marina City!
- 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 $380 per night (USD)VRBO
From $589 per night (USD)VRBO
4 Spacious Units Close to Navy Pier and Willis Tower! Parking, Pets Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $589 per night (USD)VRBO
From $148 per night (USD)VRBO
Perfect for your Chicago Getaway! Close to Midway Airport! Onsite Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $148 per night (USD)VRBO
From $148 per night (USD)VRBO
Beach Getaway! Minutes to Street Beach and Ohio Street Beach! Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $148 per night (USD)VRBO
From $558 per night (USD)VRBO
Better Choice for your Vacation! 3 Convenient Units, Close to Chicago Riverwalk
- 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 $558 per night (USD)VRBO
From $294 per night (USD)VRBO
Group Vacation! 2 Spacious Units Near Oak Street Beach! Onsite Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $294 per night (USD)VRBO
From $1173 per night (USD)VRBO
Longterm living in Chicago: 3BR Luxury Lakefront@Oak St Beach--pool, gym, decks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to this luxury 2200sf condo in Chicago, on a high floor with lake views, pool and deck. This gorgeous condo boast ...
From $1173 per night (USD)VRBO
From $255 per night (USD)Expedia
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Nestled in the heart of Chicago, this delightful apartment offers a tranquil escape for guests. With a cozy bedroom feat ...
From $255 per night (USD)Expedia
From $449 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 seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $449 per night (USD)VRBO
From $291 per night (USD)VRBO
Luxurious King Suite Offering Comfort and Style in Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 398 sq. ft, equipped with complimentary toiletries, high defi ...
From $291 per night (USD)VRBO
From $302 per night (USD)VRBO
Relax in a Spacious King Suite with Stunning Views of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 395 sq. ft, equipped with complimentary toiletries, high defi ...
From $302 per night (USD)VRBO
From $301 per night (USD)VRBO
Reliance King Suite at Staypineapple, An Iconic Hotel, The Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 395 sq. ft, equipped with complimentary toiletries, high defi ...
From $301 per night (USD)VRBO
From $291 per night (USD)VRBO
Millennium Park King Suite at Staypineapple, An Iconic Hotel, The Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 398 sq. ft, equipped with complimentary toiletries, high defi ...
From $291 per night (USD)VRBO
From $193 per night (USD)Expedia
Blueground | The Loop, pool & gym, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...
From $193 per night (USD)Expedia
From $459 per night (USD)VRBO
Panoramic 2BR Penthouse in the Sky | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $459 per night (USD)VRBO
From $116 per night (USD)Expedia
Blueground | River North, pool & gym, nr Mart
- 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 ...
From $116 per night (USD)Expedia
From $892 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 $892 per night (USD)VRBO
From $161 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 $161 per night (USD)VRBO
From $143 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 $143 per night (USD)VRBO
From $124 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 $124 per night (USD)VRBO
From $94 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 $94 per night (USD)VRBO
From $41 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 $41 per night (USD)VRBO
From $127 per night (USD)VRBO
Blueground | Near North, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Near North furnished one bedroom apar ...
From $127 per night (USD)VRBO
From $202 per night (USD)Expedia
Blueground | Streeterville, pool, nr Navy Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...
From $202 per night (USD)Expedia
From $331 per night (USD)VRBO
Vintage Downtown Penthouse, Safe #6 +gym&balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to Millennium Park, S ...
From $331 per night (USD)VRBO
From $2050 per night (USD)Expedia
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 25
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $2050 per night (USD)Expedia
From $288 per night (USD)VRBO
Fun Downtown Penthouse #3 | Vintage +balcony&gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $288 per night (USD)VRBO
From $90 per night (USD)Expedia
Budget-Friendly Room| 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 $90 per night (USD)Expedia
From $441 per night (USD)VRBO
River North | Rooftop With In & Out Parking | 3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, two ...
From $441 per night (USD)VRBO
From $220 per night (USD)Expedia
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 $220 per night (USD)Expedia
From $303 per night (USD)VRBO
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 $303 per night (USD)VRBO
From $542 per night (USD)Expedia
South Loop | Rooftop With In & Out Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bat ...
From $542 per night (USD)Expedia
From $316 per night (USD)VRBO
River North | Rooftop With In & Out Parking | 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $316 per night (USD)VRBO
From $439 per night (USD)Expedia
South Loop | Rooftop With In & Out Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bat ...
From $439 per night (USD)Expedia
From $410 per night (USD)VRBO
River North | Rooftop With In & Out Parking | 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, two ...
From $410 per night (USD)VRBO
From $360 per night (USD)Expedia
River North | Private Balcony With In&Out Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $360 per night (USD)Expedia
From $351 per night (USD)VRBO
River North | Rooftop With In & Out Parking | 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $351 per night (USD)VRBO
From $687 per night (USD)Expedia
River North Private Deck With In and Out Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, on ...
From $687 per night (USD)Expedia
From $1225 per night (USD)VRBO
Front Row to the Lake & Skyline: Epic 60th Flr 3BR
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Designed for a truly top-tier Chicago experience, 'The Observatory' is your luxurious 3BR retreat with unparall ...
From $1225 per night (USD)VRBO
From $713 per night (USD)Expedia
Luxe 67th Flr 2BR: Endless Lake Views, Top Skydeck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Discover 'The Horizon'—a new luxury 2BR apartment perfect for guests aged seeking stunning lake views and prime ...
From $713 per night (USD)Expedia
From $2428 per night (USD)VRBO
Luxury High-Floor Retreats + Lake Views
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 17
Summary: 'The Crest' is the ultimate group solution: three new high-floor apartments with jaw-dropping lake and city vie ...
From $2428 per night (USD)VRBO
From $135 per night (USD)VRBO
Short Drive to Millennium Park & Willis Tower with Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $135 per night (USD)VRBO
From $289 per night (USD)VRBO
Dip into Heated Pool & Relax in 2 Modern Rooms | Walk to Chicago Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 2 separate rooms withi ...
From $289 per night (USD)VRBO
From $289 per night (USD)VRBO
2 Boutique-Style Rooms | Indoor Pool, Gym, & Near Magnificent Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 2 separate rooms withi ...
From $289 per night (USD)VRBO
From $136 per night (USD)VRBO
Stay Cool w/ Rooftop Deck & Fitness Room Near Chicago Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $136 per night (USD)VRBO
From $144 per night (USD)VRBO
Rooftop Relaxation w/ Pool + Gym | Walk to Millennium Park and Chicago Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $144 per night (USD)VRBO
From $144 per night (USD)VRBO
Stay in Heart of Chicago | Rooftop Deck, Gym and Near Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $144 per night (USD)VRBO
From $3123 per night (USD)VRBO
Premium Lake Views + Ideal for Group Getaways
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 22
Summary: Discover 'The Skye'—a luxury multi-unit collection perfect for group retreats with breathtaking views of Grant ...
From $3123 per night (USD)VRBO
From $640 per night (USD)VRBO
43rd-Floor Luxury Escape + Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Elevate your Chicago getaway at 'The Zenith,' a 43rd-floor retreat for those who appreciate world-class ameniti ...
From $640 per night (USD)VRBO
From $625 per night (USD)Expedia
49th Fl Luxury Retreat + Stunning Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience modern luxury at 'The Summit', ideal for families seeking exceptional amenities and nearby attractio ...
From $625 per night (USD)Expedia
From $191 per night (USD)VRBO
La Quinta – Deluxe King Room with City Views in Chicago Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Surrounded by iconic architecture and vibrant dining, La Quinta Chicago offers city access and skyline views in the Loop ...
From $191 per night (USD)VRBO
From $189 per night (USD)VRBO
La Quinta – King Suite with Living Area Near Chicago Landmarks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just off Wacker Drive, La Quinta provides easy access to Union Station and the Magnificent Mile. This non-smoking king s ...
From $189 per night (USD)VRBO
From $91 per night (USD)VRBO
Blueground | Streeterville, rooftop pool, nr Navy Pier
- 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 $91 per night (USD)VRBO
From $676 per night (USD)Expedia
Cultural Mile 2BR, A Stay in the Sky, 65th Floor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Ideal for families & friends seeking stunning views and luxury amenities in 'The Peak.' Be one of the first t ...
From $676 per night (USD)Expedia
From $636 per night (USD)VRBO
60th Flr Lake Views, A Stay Above It All, Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: For travelers wanting an exciting experience, 'The Starlight' is a stylish 60th-floor home with amazing views a ...
From $636 per night (USD)VRBO
From $130 per night (USD)Expedia
Fully Furnished Gold Coast Luxury Condo with Sunset View Ideal for 30+ Day Stays
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Luxury High-Rise Condo in Chicago’s Gold Coast, Perfect for Long-Term Stays Experience upscale city living in this full ...
From $130 per night (USD)Expedia
From $579 per night (USD)VRBO
Group Vacation! 4 Comfortable Units, Indoor Pool, Rooftop Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 4 separate rooms withi ...
From $579 per night (USD)VRBO
From $290 per night (USD)VRBO
2 Spacious Units Close to Navy Pier! Pool, Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $290 per night (USD)VRBO
From $436 per night (USD)VRBO
Your Chicago Adventure Starts Here! 3 Units! Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $436 per night (USD)VRBO
From $146 per night (USD)VRBO
Large Unit Close to the Millennium Park! Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $146 per night (USD)VRBO
From $2617 per night (USD)VRBO
4 Luxury 2BRs, Stay Together in Style, For Groups
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: Traveling with a large group? 'The Lumen' offers four modern 2BR apartments, providing the perfect blend of tog ...
From $2617 per night (USD)VRBO
From $1061 per night (USD)VRBO
High-Floor 2BRs with City & Lake Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Bring your whole group to 'The Apex,' our collection of two high-floor 2BRs, offering the perfect blend of toge ...
From $1061 per night (USD)VRBO
From $2553 per night (USD)VRBO
2BRs w/ Lakefront Views, Sleeps Large Groups
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Summary: Perfect for groups, ‘The Vista’ offers sky-high 2BRs with breathtaking lake and city views plus access to Chica ...
From $2553 per night (USD)VRBO
From $692 per night (USD)Expedia
Elevated 2BR Retreat + Balcony with Bean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience luxury in 'The Luma,' a prime 2BR in the Loop with breathtaking views, perfect for city explorers. W ...
From $692 per night (USD)Expedia
From $111 per night (USD)VRBO
Luxury 1BR Condo – Views, Comfort, & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home—an upscale, sun-filled 1-bedroom condo located on the 41st floor in the heart of Chi ...
From $111 per night (USD)VRBO
From $317 per night (USD)VRBO
2 Spacious Rooms with 2 Queen Beds Near Magnificent Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $317 per night (USD)VRBO
From $125 per night (USD)VRBO
Downtown Living: Walkable, Modern Chicago Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Remote Work Ready | Willis Tower View | On-Site Market Stay in the Loop — where every meeting, meal, and museum is just ...
From $125 per night (USD)VRBO
From $183 per night (USD)Expedia
Modern Elegance meets Chicago High Rise 1-bedroom apt with a breathtaking view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Luxurious 1 Bedroom at 1000M - Grant Park; Millennium Park, Navy Pier & Lake Michigan! Sleeps up to 5 adults (queen be ...
From $183 per night (USD)Expedia
From $138 per night (USD)VRBO
Pet Friendly Queen Unit! Near Chicago Attractions!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a great location in a trendy neighborhood near shopping, dining, and attractions, this is the perfect spot for your ...
From $138 per night (USD)VRBO
From $175 per night (USD)VRBO
Modern Queen Stay! Pet Friendly Accommodation w/ Gym Access | Chicago Riverwalk!
- 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 $175 per night (USD)VRBO
From $144 per night (USD)VRBO
River North Chicago Chic w/King Bed - Lake & Skyline Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unbeatable River North location just steps from Michigan Avenue, Northwestern Medical Center and Loyola. This full cond ...
From $144 per night (USD)VRBO
From $344 per night (USD)VRBO
1BR Apt l Sentral Michigan Ave l Walk to Museums & Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience downtown Chicago with ease from this modern one-bedroom apartment at Sentral Michigan Avenue. Enjoy home-cook ...
From $344 per night (USD)VRBO
From $444 per night (USD)VRBO
Sentral Michigan Ave l 2BR Apt l Ideal for Family or Friends
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located just steps from Lake Michigan and Grant Park, this two-bedroom unit offers spacious comfort in the middle of it ...
From $444 per night (USD)VRBO
From $366 per night (USD)VRBO
Sentral Michigan Ave l 1BR + Den l Flexible Work & Stay Space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Settle into your Chicago home away from home with this 1-bedroom apartment plus den in the heart of the South Loop. Idea ...
From $366 per night (USD)VRBO