Chicago Harbor Rentals
From $291 per night (USD)VRBO
Downtown 2bd #6 +Gym near Park, Lake, Museums
- 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 $291 per night (USD)VRBO
From $291 per night (USD)Expedia
Downtown 2bd #5 +Gym near Park, Lake, Museums
- 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 $291 per night (USD)Expedia
From $410 per night (USD)VRBO
Downtown 3bd #7 near Park+Museums
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $410 per night (USD)VRBO
From $292 per night (USD)Expedia
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 $292 per night (USD)Expedia
From $1620 per night (USD)VRBO
3 Stylish 2BRs Steps from Magnificent Mile
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Summary: Designed for a comfortable group getaway, 'The Mary' offers a modern and spacious retreat in the renowned Gold ...
From $1620 per night (USD)VRBO
From $1388 per night (USD)VRBO
High-end Luxury Units + Iconic Views for Groups
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: Ideal for groups, 'The Apollo' offers two stylish apartments in a prime location, just steps from Chicago's bes ...
From $1388 per night (USD)VRBO
From $551 per night (USD)VRBO
Two 2BRs Near Millennium Park, Ideal for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Gather your favorite people at 'The Winfrey,' our exclusive offering of two luxury apartments, perfect for your ...
From $551 per night (USD)VRBO
From $1153 per night (USD)VRBO
Gold Coast Group Retreat + Breathtaking Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Discover the perfect group retreat in Chicago's Gold Coast, a collection of two modern 2BR apartments with priv ...
From $1153 per night (USD)VRBO
From $114 per night (USD)VRBO
Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground
- 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 $114 per night (USD)VRBO
From $1520 per night (USD)Expedia
PH w/ Bean & Lake Views, An Elite Stay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The ...
From $1520 per night (USD)Expedia
From $4468 per night (USD)VRBO
Iconic Downtown Penthouses Getaway + City Views
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
Summary: 'The Lyra' pairs two exquisite penthouses for a unique Chicago experience perfect for groups seeking both leisu ...
From $4468 per night (USD)VRBO
From $96 per night (USD)Expedia
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 $96 per night (USD)Expedia
From $512 per night (USD)VRBO
Blueground | River North 2bd apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished two bedroo ...
From $512 per night (USD)VRBO
From $132 per night (USD)Expedia
Blueground | South Loop 1bd apartment
- 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 $132 per night (USD)Expedia
From $238 per night (USD)VRBO
Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $410 per night (USD)VRBO
Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units
- 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 $410 per night (USD)VRBO
From $410 per night (USD)VRBO
2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park
- 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 $410 per night (USD)VRBO
From $197 per night (USD)VRBO
Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park
- 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 $529 per night (USD)VRBO
Luxury Designer Penthouse|Private Deck|Gold Coast
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's ce ...
From $529 per night (USD)VRBO
From $96 per night (USD)Expedia
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)Expedia
From $104 per night (USD)VRBO
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)VRBO
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 $295 per night (USD)VRBO
2 Sleek Eco-friendly Rooms w/ Natural Furnishings in Vibrant River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $295 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
Click For PricingExpedia
City View Smart, luxurious 1bd apartment - Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
City View Smart, luxurious 1BD apartment with stunning Chicago skyline views, a personalized Pilates reformer, and centr ...
Click For PricingExpedia
From $257 per night (USD)VRBO
South Loop 3 Bedroom Apt
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: South Loop 3 bedroom apartment with 1 bathroom. We are centrally located and very easy to get anywhere in the c ...
From $257 per night (USD)VRBO
From $264 per night (USD)VRBO
South Loop 2 Bedroom Apt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 13
Summary: South Loop 2 bedroom apartment with 2 bathrooms. We are centrally located and very easy to get anywhere in the ...
From $264 per night (USD)VRBO
From $203 per night (USD)VRBO
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)VRBO
From $758 per night (USD)Expedia
HUGE 4Br with POOL TABLE and optional parking/sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $758 per night (USD)Expedia
From $353 per night (USD)VRBO
McCormick Place 2b/2b corner unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $353 per night (USD)VRBO
From $325 per night (USD)Expedia
McCormick Place Skyline view 2br/2ba with optional parking for up to 8 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • 2 shifts Security officers in the building • 2 ...
From $325 per night (USD)Expedia
From $121 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 $121 per night (USD)VRBO
From $446 per night (USD)Expedia
McCormick Place luxurious 3b/2ba Family Heaven with optional parking/sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $446 per night (USD)Expedia
From $370 per night (USD)VRBO
McCormick Place Stylish corner unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $370 per night (USD)VRBO
From $460 per night (USD)Expedia
Spacious and luxurious apartment / sleeps 10 and with optional parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $460 per night (USD)Expedia
From $445 per night (USD)VRBO
McCormick 3B/2Ba Corner Oasis for up to 10 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $445 per night (USD)VRBO
From $339 per night (USD)Expedia
McCormick Place 2b/2b family unit with optional parking for up to 8 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Amazing City view • ...
From $339 per night (USD)Expedia
From $1038 per night (USD)VRBO
McCormick 5B/3Ba Luxury Suite for groups/12 guests
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • 2609 sq f Luxurious unit for large groups • 5 ...
From $1038 per night (USD)VRBO
From $489 per night (USD)Expedia
McCormick Place 3b/2b family oasis with optional parking for up to 10 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $489 per night (USD)Expedia
From $459 per night (USD)VRBO
McCormick Place Designer 3b/2b family heaven with optional parking/Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $459 per night (USD)VRBO
From $223 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 $223 per night (USD)Expedia
From $146 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 $146 per night (USD)VRBO
From $668 per night (USD)Expedia
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 $668 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 $841 per night (USD)Expedia
McCormick 6B/4Ba Luxury Suite for groups of up to 12 guests w/ optional parking
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • 1900 sq f Luxurious unit for large groups • 6 ...
From $841 per night (USD)Expedia
From $469 per night (USD)VRBO
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)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 $370 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 $370 per night (USD)VRBO
From $259 per night (USD)Expedia
Gold Coast 2 Bedroom Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern 2BR Retreat in Gold Coast – Stylish & Newly Renovated! Experience the best of Chicago’s Gold Coast in this brand ...
From $259 per night (USD)Expedia
From $1356 per night (USD)VRBO
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 26
RENT WITH CONFIDENCE FROM A PREMIER HOST WITH OVER 800 POSITIVE REVIEWS! One-of-a-kind opportunity to rent a historic Gi ...
From $1356 per night (USD)VRBO
From $187 per night (USD)VRBO
Heart of Chicago, Double Queen @ The Chicago Hotel Collection Magnificent Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $187 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
From $167 per night (USD)VRBO
City Center Luxury, Double Queen - The Chicago Hotel Collection Mag Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $167 per night (USD)VRBO
From $83 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
- 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 $83 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $141 per night (USD)VRBO
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 sophisticated Near North furnished one bedroo ...
From $141 per night (USD)VRBO
From $725 per night (USD)Expedia
McCormick 6B/4Ba Luxury Suite for groups/12 guests
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • 1850 sq f Luxurious unit for large groups • 6 ...
From $725 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 $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 $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 $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 $1020 per night (USD)VRBO
Beautiful Unit CHI in Prime River North - top floor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This beautiful unit located on the top floor in downtown is perfect for families, children and corporate gather ...
From $1020 per night (USD)VRBO
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 $428 per night (USD)VRBO
Luxury Designer Penthouse | Gold Coast/Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own penthouse in Chicago's Gold Coast and Ol ...
From $428 per night (USD)VRBO
From $218 per night (USD)Expedia
Chic 2-Bedroom Condo in Gold Coast – Modern & Newl
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the elegance of Chicago’s iconic Gold Coast neighborhood in this newly rehabbed, modern 2-bedroom condo. Thou ...
From $218 per night (USD)Expedia
From $286 per night (USD)VRBO
2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Modern 2-bedroom apartment in Chicago’s peaceful South Loop. Located across from McCormick Place and Wintrust Stadium, ...
From $286 per night (USD)VRBO
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 $41 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 $41 per night (USD)VRBO
From $1454 per night (USD)VRBO
Luxury Designer Penthouse Combo | NW | Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1454 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 $249 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 $249 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 $253 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 $253 per night (USD)VRBO
From $249 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 $249 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 $127 per night (USD)Expedia
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)Expedia
From $202 per night (USD)VRBO
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)VRBO
From $331 per night (USD)Expedia
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)Expedia
From $2050 per night (USD)VRBO
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)VRBO
From $288 per night (USD)Expedia
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)Expedia
From $90 per night (USD)VRBO
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)VRBO
From $441 per night (USD)Expedia
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)Expedia
From $84 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 $84 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