Top Vacation rentals in Chicago Metropolitan Area
Find the Top Vacation rentals in Chicago Metropolitan Area – 20+ Quality Options from Leading Providers
1-20 out of 28 vacation rentals
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Holiday home
From
US$ 793
/night
- Five-bedroom holiday home with patio
- Grocery delivery and barbecue facilities
- Access to skiing and hiking activities
Holiday home
26 adults
7 bedrooms
9 beds
From
US$ 1 552
/night
- Beachfront property with lake views
- Hot tub/Jacuzzi for relaxation
- Family rooms with various amenities
Holiday home
- Private Beach
- Fitness Centre
- Children's Playground
From
US$ 508
/night
- Private beach access for exclusive relaxation
- On-site fitness classes and activities available
- Family-friendly restaurant with outdoor dining
- Driveway Parking
- Outdoor Dining
- Pet-Friendly
- 5 bedrooms accommodate large groups
- Driveway parking available for guests
- Outdoor dining area for gatherings
Holiday home
- Private Entrance
- Electric Charging
- Flat-Screen TV
From
US$ 1 891
/night
- Five spacious bedrooms for families
- Private entrance for added privacy
- Electric vehicle charging station available
Lodge
- Business Centre
- Free Parking
- Breakfast Options
From
US$ 49
/night
- 24-hour business centre with services
- Buffet or continental breakfast offered
- Free private parking available onsite
- Air Conditioning
- Flat-Screen TV
- Private Entrance
From
US$ 107
/night
- Private entrance for added privacy
- Streaming services on flat-screen TV
- Fully equipped kitchen with utensils
Holiday home
- Outdoor dining
- Private check-in
- Picnic area
From
US$ 480
/night
- Private entrance for added privacy
- Fully equipped kitchen for cooking meals
- Outdoor dining area with garden views
Apartment
- Air conditioning
- Flat-screen TV
- Dining area
From
US$ 199
/night
- Fully equipped kitchen in all units
- Convenient proximity to Lincoln Park Zoo
- Family-friendly apartment options available
Apartment
- Fitness Center
- Outdoor Dining
- Game Room
From
US$ 268
/night
- Fully equipped kitchens in all units
- Diverse outdoor activities available nearby
- On-site fitness center access
- Flat-screen TV
- Picnic area
- Air conditioning
From
US$ 376
/night
- Five bedrooms with flat-screen TV
- Fully equipped kitchen with dishwasher
- Free parking and secure entry
- Rooftop Pool
- Sun Terrace
- Fitness Centre
From
US$ 266
/night
- Rooftop pool with stunning views
- Fully equipped kitchens in apartments
- 24-hour front desk service
Apartment
- Flat-screen TV
- Air conditioning
- Golf course
From
US$ 199
/night
- Private entrance for enhanced privacy
- Fully equipped kitchen with modern appliances
- Golf course available for leisure activities
Holiday home
- Lake Views
- Fireplace
- Swimming Pool
From
US$ 182
/night
- Stunning lake and sea views
- Cozy fireplace for comfort
- Inviting on-site swimming pool
- Rooftop pool
- Private parking
- Garden area
From
US$ 585
/night
- Rooftop pool with seasonal access
- Modern apartments with full kitchens
- Close to local attractions and beaches
- Fully equipped kitchen
- Outdoor dining area
- Picnic area
From
US$ 106
/night
- Outdoor dining area with picnic space
- Free private parking for guests
- Equipped kitchen for self-catering
- Outdoor dining
- Speakeasy bar
- Fully equipped kitchen
From
US$ 237
/night
- On-site speakeasy for unique nightlife
- Fully equipped kitchen for convenience
- Outdoor dining area for relaxation
Holiday home
- Private Entrance
- Flat-Screen TV
- Fully Equipped Kitchen
From
US$ 112
/night
- Private entrance for added privacy
- Flat-screen TV with cable channels
- Fully equipped kitchen for cooking
- Equipped Kitchen
- Flat-screen TV
- Air Conditioning
From
US$ 165
/night
- Fully equipped kitchen with an oven
- Located near Wrigley Field for activities
- Streaming services on flat-screen TV
- Private Parking
- Flat-Screen TV
- Air Conditioning
From
US$ 538
/night
- 3 bedrooms and 2 bathrooms for families
- Fully equipped kitchen for convenient meals
- Private parking available on site
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