
Sled Hill Prairie Rentals

- From $453 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 $453 per night (USD)VRBO
- From $474 per night (USD)
Expedia
McCormick 420-Friendly 3BR/2BA with Optional Parking - State St.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• MESSAGE US for SPECIAL RATES • State street location • Minutes walk to McCormick Convention Center • 4K Roku HDTVs in ...
From $474 per night (USD)Expedia
- From $456 per night (USD)
VRBO
McCormick 3BR-2BA 420-Friendly with Optional Parking - State st.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• MESSAGE US for SPECIAL RATES • Smoking allowed inside • State street location • Minutes walk to McCormick Convention C ...
From $456 per night (USD)VRBO
- From $119 per night (USD)
Expedia
Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Your cozy getaway awaits in Chicago at this enchanting condo. With 2 welcoming bedrooms featuring queen beds and 2 seren ...
From $119 per night (USD)Expedia
- From $431 per night (USD)
VRBO
McCormick Cozy 3Bedroom with Optional Parking for 8 guests
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
• MESSAGE US for SPECIAL RATES • State street location • Minutes walk to McCormick Convention Center • 4K Roku HDTVs in ...
From $431 per night (USD)VRBO
- From $443 per night (USD)
Expedia
Spacious 3BR in South Loop Near McCormick - Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 2-bath apartment perfect for everyone! Just minutes ...
From $443 per night (USD)Expedia
- From $134 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 comfortable South Loop furnished one bedroom ...
From $134 per night (USD)VRBO
- From $320 per night (USD)
Expedia
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)Expedia
- From $327 per night (USD)
VRBO
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)VRBO
- From $228 per night (USD)
Expedia
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)Expedia
- From $283 per night (USD)
VRBO
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)VRBO
- From $303 per night (USD)
Expedia
Blueground | South Loop, pool & gym, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with views over the city. It’ll be easy to s ...
From $303 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Blueground | Central Station, pool, nr Grant 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)VRBO
- From $188 per night (USD)
Expedia
Blueground | Central Station, pool, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Central Station. It’ll be easy to simply show up and start l ...
From $188 per night (USD)Expedia
- From $430 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 $430 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Cozy Private Room in Prime Downtown 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 $125 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 $431 per night (USD)
VRBO
Stylish 4BR Stay-Prime Location - State rep
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This spacious 4-bedroom apartment is located in the vibrant and historic State Street area, just minutes from s ...
From $431 per night (USD)VRBO
- From $437 per night (USD)
Expedia
Stylish 4BR South Loop Home State 23-202
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience Chicago in style at our beautifully furnished four-bedroom house, complete with three full bathrooms ...
From $437 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Smart Simple and Spacious 4BR Apt State 203
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Flexible, functional, and fully furnished – this 4BR is ready for you. The Space: Settle into our inviting 4-b ...
From $435 per night (USD)VRBO
- From $1339 per night (USD)
Expedia
Sky-High Living: Lake Views, Elite Experience
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Ascend to 'The Observatory', a brand-new 3-bedroom luxury apartment on the 60th floor, where spectacular lake v ...
From $1339 per night (USD)Expedia
- From $853 per night (USD)
VRBO
Lux 67Fl Apt: Lake Views, Top Residential Sky Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Be one of the first to discover 'The Horizon,' a brand-new 2-bedroom luxury apartment on the 67th floor. Enjoy ...
From $853 per night (USD)VRBO
- From $3069 per night (USD)
VRBO
Prime Group Stay: Lake Views, Luxe Amenities
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 17
Summary: Elevate your group's visit at 'The Crest', a brand-new luxury stay offering three high-floor apartments with ja ...
From $3069 per night (USD)VRBO
- From $765 per night (USD)
VRBO
Penthouse Oasis With Wrap-Around Balcony & Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience luxury and versatility in this stunning 32nd-floor penthouse, featuring a spectacular wrap-around balcony wit ...
From $765 per night (USD)VRBO
- From $5118 per night (USD)
VRBO
Panoramic Lake Views: Premier Amenities for Groups
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 22
Summary: Find your ideal group getaway at 'The Skye', our new multi-unit collection. These apartments offer stunning lak ...
From $5118 per night (USD)VRBO
- From $811 per night (USD)
VRBO
43 Fl World-Class Escape w/Breathtaking Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Settle into a new level of luxury at 'The Zenith', a 43rd-floor retreat with sweeping views of the city and lak ...
From $811 per night (USD)VRBO
- From $821 per night (USD)
Expedia
Top-Tier Stay: 49th Fl, Lakefront & City Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience elevated living at The Summit, where stunning lakefront views meet modern luxury. This brand-new apa ...
From $821 per night (USD)Expedia
- From $373 per night (USD)
VRBO
Spacious 2BR Unit Skyline View - Walk to McCormick
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome and Experience modern comfort just minutes from downtown. Our 2-bedroom, 2-bath suite features city views, high ...
From $373 per night (USD)VRBO
- From $250 per night (USD)
Expedia
McCormick Place Studio/Optional parking/sleeps up to 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $250 per night (USD)Expedia
- From $355 per night (USD)
VRBO
McCormick 2B/2Ba for up to 8 guests with Skyline view and Optional parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $355 per night (USD)VRBO
- From $905 per night (USD)
Expedia
Spacious 5BR Luxury Suite - Near McCormick Place
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the Michigan Suite — a modern and luxurious 5-bedroom, 3-bathroom apartment located in the heart of South Loo ...
From $905 per night (USD)Expedia
- From $836 per night (USD)
VRBO
High-Rise 65 Fl Apt w/Lux Amenities, Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Live high above the city in 'The Peak', a stunning new apartment with captivating lake views. It offers access ...
From $836 per night (USD)VRBO
- From $856 per night (USD)
Expedia
60 Fl Lake View Apt: An Urban Oasis in the Sky
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Find your ultimate city retreat at this new 60th-floor apartment. You will have breathtaking views of the lake ...
From $856 per night (USD)Expedia
- From $575 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 $575 per night (USD)VRBO
- From $382 per night (USD)
Expedia
Spacious 2BR Group Stay near McCormick & Wintrust
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome and Experience Chicago in style at our modern, luxury 2-bedroom, 2-bathroom suite located on iconic Michigan Ave ...
From $382 per night (USD)Expedia
- From $311 per night (USD)
VRBO
2-bedroom condo in perfect Chicago with WiFi, AC. Start your getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape to a marvelous 2-bedroom condo in Chicago. This serene retreat features a king bed and a twin bed, perfect for a ...
From $311 per night (USD)VRBO
- From $404 per night (USD)
Expedia
Spacious Family-Friendly 2BR near McCormick & Zoo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your modern retreat in the heart of Chicago’s vibrant South Loop! This stylish 2-bedroom, 2-bathroom suite i ...
From $404 per night (USD)Expedia
- From $356 per night (USD)
VRBO
Stylish 2BR Cozy South Loop Suite Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your chic and cozy home in the heart of Chicago’s vibrant South Loop! Just steps away from McCormick Place, t ...
From $356 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Chic Cozy 2BR near McCormick + Museum Campus
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome and Experience Chicago in style at our modern, luxury 2-bedroom, 2-bathroom suite located on iconic Michigan Ave ...
From $418 per night (USD)Expedia
- From $378 per night (USD)
VRBO
Charming 2BR Unit Near McCormick & Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your stylish urban retreat in the heart of Chicago's vibrant South Loop! This spacious and fully-equipped 2-b ...
From $378 per night (USD)VRBO
- From $384 per night (USD)
Expedia
McCormick 2B/2Ba for up to 8 guests w Opt Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $384 per night (USD)Expedia
- From $3506 per night (USD)
VRBO
Luxury Group Escape: Top Amenities, City Views
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: Your search for the perfect group retreat ends here. 'The Lumen' presents four elite 2BR apartments designed fo ...
From $3506 per night (USD)VRBO
- From $1751 per night (USD)
VRBO
High-Floor 2BRs: 2 Units, Elite Amenities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Discover 'The Apex', our exclusive offering of two 2BR apartments in the same remarkable building. Perched on h ...
From $1751 per night (USD)VRBO
- From $2724 per night (USD)
VRBO
Top-Floor 2BRs: Unrivaled Views, Resort Living
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Summary: Welcome to 'The Vista', a premier collection of three 2BR apartments designed for large groups. Located on high ...
From $2724 per night (USD)VRBO
- Click For Pricing
Expedia
Club 1919 – Chic Urban Retreat w/ Private Patio in the Heart of Chicago
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Discover comfort, style, and unbeatable access to everything Chicago has to offer from this design-forward 1-bedroom, 1. ...
Click For PricingExpedia