Top Vacation rentals in Chicago

Find the Top Vacation rentals in Chicago – 20+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 20 vacation rentals
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10 adults
5 bedrooms
5 beds
MapView on map1.9 mi from City Center800 yd from Michigan Avenue
From   US$ 1 891 /nightSelect
  • Five spacious bedrooms for families
  • Private entrance for added privacy
  • Electric vehicle charging station available
4 adults
1 bedroom
2 beds
MapView on map3.8 mi from City Center
From   US$ 107 /nightSelect
  • Private entrance for added privacy
  • Streaming services on flat-screen TV
  • Fully equipped kitchen with utensils
  • Outdoor dining
  • Private check-in
  • Picnic area
4.9 mi from City Center
From   US$ 480 /nightSelect
  • Private entrance for added privacy
  • Fully equipped kitchen for cooking meals
  • Outdoor dining area with garden views
  • Air conditioning
  • Flat-screen TV
  • Dining area
3.7 mi from City Center
From   US$ 199 /nightSelect
  • Fully equipped kitchen in all units
  • Convenient proximity to Lincoln Park Zoo
  • Family-friendly apartment options available
  • Fitness Center
  • Outdoor Dining
  • Game Room
5.0 mi from City Center
From   US$ 268 /nightSelect
  • Fully equipped kitchens in all units
  • Diverse outdoor activities available nearby
  • On-site fitness center access
  • Flat-screen TV
  • Picnic area
  • Air conditioning
4.2 mi from City Center
From   US$ 376 /nightSelect
  • Five bedrooms with flat-screen TV
  • Fully equipped kitchen with dishwasher
  • Free parking and secure entry
  • Rooftop Pool
  • Sun Terrace
  • Fitness Centre
1.5 mi from City Center700 yd from Michigan Avenue
From   US$ 266 /nightSelect
  • Rooftop pool with stunning views
  • Fully equipped kitchens in apartments
  • 24-hour front desk service
  • Flat-screen TV
  • Air conditioning
  • Golf course
8.7 mi from City Center
From   US$ 199 /nightSelect
  • Private entrance for enhanced privacy
  • Fully equipped kitchen with modern appliances
  • Golf course available for leisure activities
  • Rooftop pool
  • Private parking
  • Garden area
1.5 mi from City Center300 yd from Michigan Avenue
From   US$ 585 /nightSelect
  • Rooftop pool with seasonal access
  • Modern apartments with full kitchens
  • Close to local attractions and beaches
  • Fully equipped kitchen
  • Outdoor dining area
  • Picnic area
6.2 mi from City Center
From   US$ 106 /nightSelect
  • Outdoor dining area with picnic space
  • Free private parking for guests
  • Equipped kitchen for self-catering
  • Equipped Kitchen
  • Flat-screen TV
  • Air Conditioning
4.6 mi from City Center1700 yd from Wrigley Field
From   US$ 165 /nightSelect
  • Fully equipped kitchen with an oven
  • Located near Wrigley Field for activities
  • Streaming services on flat-screen TV
  • Outdoor dining
  • Speakeasy bar
  • Fully equipped kitchen
3.3 mi from City Center
From   US$ 237 /nightSelect
  • On-site speakeasy for unique nightlife
  • Fully equipped kitchen for convenience
  • Outdoor dining area for relaxation
  • Private Entrance
  • Flat-Screen TV
  • Fully Equipped Kitchen
12.0 mi from City Center
From   US$ 112 /nightSelect
  • Private entrance for added privacy
  • Flat-screen TV with cable channels
  • Fully equipped kitchen for cooking
  • Flat-screen TV
  • Fully equipped kitchen
  • Washing machine
2.6 mi from City Center
From   US$ 728 /nightSelect
  • Close to popular bars and restaurants
  • Fully equipped kitchen with modern appliances
  • Flat-screen TV for entertainment
  • Private Parking
  • Flat-Screen TV
  • Air Conditioning
1.6 mi from City Center1000 yd from McCormick Place
From   US$ 538 /nightSelect
  • 3 bedrooms and 2 bathrooms for families
  • Fully equipped kitchen for convenient meals
  • Private parking available on site
  • Outdoor Pool
  • Fully Equipped Kitchen
  • Sun Terrace
1700 yd from City Center1400 yd from Chicago Union Station
From   US$ 283 /nightSelect
  • Stunning city views from all apartments
  • Seasonal outdoor pool and sun terrace
  • Fully equipped kitchens in every unit
Apartment
  • Garden
  • Barbecue
  • Fireplace
3.2 mi from City Center
From   US$ 232 /nightSelect
  • Private terrace with garden views
  • On-site cycling and fishing activities
  • Children's playground on property
  • Private Parking
  • Fully Equipped Kitchen
  • Garden Terrace
1.9 mi from City Center1200 yd from Michigan Avenue
From   US$ 442 /nightSelect
  • Garden views from spacious balcony
  • Free private parking for guests
  • Pet-friendly accommodations available
1.7 mi from City Center800 yd from McCormick Place
From   US$ 887 /nightSelect
Nestled in South Loop district of the city, the venue is about 10 miles from Midway International airport.
  • Air conditioning
  • Washing machine
  • TV
10.4 mi from City Center
From   US$ 159 /nightSelect
  • Private entrance for enhanced privacy
  • Fully equipped kitchen with cookware
  • Non-smoking property for clean atmosphere