Chicago Harbor, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chicago Harbor, Illinois on RentalSaver.com!

Chicago Harbor Rentals

From $1228 per night (USD)
VRBO
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 $1228 per night (USD)
VRBO
From $835 per night (USD)
Expedia
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 $835 per night (USD)
Expedia
From $2998 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 $2998 per night (USD)
VRBO
From $765 per night (USD)
Expedia
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)
Expedia
From $171 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 $171 per night (USD)
VRBO
From $350 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 $350 per night (USD)
VRBO
From $344 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 $344 per night (USD)
VRBO
From $171 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 $171 per night (USD)
VRBO
From $175 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 $175 per night (USD)
VRBO
From $175 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 $175 per night (USD)
VRBO
From $5004 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 $5004 per night (USD)
VRBO
From $783 per night (USD)
Expedia
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 $783 per night (USD)
Expedia
From $800 per night (USD)
VRBO
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 $800 per night (USD)
VRBO
From $376 per night (USD)
Expedia
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 $376 per night (USD)
Expedia
Click For Pricing
VRBO
Skyline 2BR in South Loop Chicago Near McCormick
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just step ...
Click For Pricing
VRBO
From $342 per night (USD)
Expedia
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 $342 per night (USD)
Expedia
From $145 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 $145 per night (USD)
VRBO
From $816 per night (USD)
Expedia
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 $816 per night (USD)
Expedia
From $813 per night (USD)
VRBO
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 $813 per night (USD)
VRBO
From $574 per night (USD)
Expedia
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 $574 per night (USD)
Expedia
From $413 per night (USD)
VRBO
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 $413 per night (USD)
VRBO
Click For Pricing
Expedia
Downtown Walk-In Retreat | 5 Mins to River & Shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Stay in style at this modern River North retreat—steps from CTA, shops, and dining. Just 5 mins to Magnificent ...
Click For Pricing
Expedia
From $134 per night (USD)
VRBO
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 $134 per night (USD)
VRBO
From $311 per night (USD)
Expedia
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)
Expedia
From $669 per night (USD)
VRBO
Designer Apartment 2E | Heart of Gold Coast/River North
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Chica ...
From $669 per night (USD)
VRBO
From $789 per night (USD)
Expedia
Designer Apartment 2W | Heart of Gold Coast/River North
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Chica ...
From $789 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Secret Gallery on the Park - 2bd/1ba + 1bd/1ba
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $506 per night (USD)
VRBO
From $340 per night (USD)
Expedia
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 $340 per night (USD)
Expedia
From $386 per night (USD)
VRBO
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 $386 per night (USD)
VRBO
From $361 per night (USD)
Expedia
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 $361 per night (USD)
Expedia
From $699 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 $699 per night (USD)
VRBO
From $350 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 $350 per night (USD)
VRBO
From $524 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 $524 per night (USD)
VRBO
From $175 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 $175 per night (USD)
VRBO
From $3380 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 $3380 per night (USD)
VRBO
From $1709 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 $1709 per night (USD)
VRBO
From $2647 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 $2647 per night (USD)
VRBO
From $833 per night (USD)
Expedia
Top-Notch 2BR: The Bean View, Loop, Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your perfect home for an unforgettable stay awaits at 'The Luma', a luxurious 2BR apartment with iconic views o ...
From $833 per night (USD)
Expedia
From $103 per night (USD)
VRBO
Luxury 1BR Condo – Views, Comfort, & Style
Bedrooms:
1
Bathrooms:
2
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 $103 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Stroll Anywhere! 5 mins to Riverwalk & Mag Mile
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Enjoy Chicago from this stylish River North gem—steps from top dining, nightlife, and attractions. Just 2 mins ...
From $382 per night (USD)
Expedia
Click For Pricing
VRBO
Club 1919 – Chic Urban Retreat w/ Private Patio in the Heart of Chicago
Bedrooms:
1
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 Pricing
VRBO
From $137 per night (USD)
Expedia
Blueground | Rush & Division, balcony, nr Lake Shore Park
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 $137 per night (USD)
Expedia
From $892 per night (USD)
VRBO
Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect Chicago getaway at 111 W Elm St — where classic elegance meets modern comfort in the heart of th ...
From $892 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Stay in the heart of River North—steps from dining, nightlife, and attractions. Just 2 mins to CTA, 5 mins to M ...
From $347 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Boulevard Stays | 5 Minutes to Magnificent Mile and River North
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience chic comfort in this modern River North retreat—just 5 minutes from the Magnificent Mile, CTA, top d ...
From $294 per night (USD)
VRBO

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Chicago Harbor Rentals

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Results: 945 Rentals