Find and Book Top Rated Holiday rentals in Chicago

Search among 6 available holiday rentals in Chicago from 50+ providers

Check-in
Select date
Check-out
Select date
Rooms & Guests
22 Guests, 1 Room
1Filter & Sort
View map
1-6 out of 6
1Filter & Sort
View map
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8 adults
3 bedrooms
5 beds
MapView on map7.9 km from City Centre500 m from Viaduct Center
From   US$ 273 /nightSelect
7.8
Very good1 review
10 adults
1 bedroom
3 beds
MapView on map8.0 km from City Centre800 m from
From   US$ 188 /nightSelect
7.0
Very good1 review
5.7 km from City Centre800 m from
From   US$ 133 /nightSelect
Apartment
9.8
Perfect1 review
5.1 km from City Centre300 m from Lincoln Park Hospital
From   US$ 169 /nightSelect
10.0 km from City Centre600 m from Applied Research Technical
From   US$ 81 /nightSelect
2.5 km from City Centre600 m from Michigan Avenue
From   US$ 385 /nightSelect

Best Vacation Rentals in Chicago

Why visit?

Chicago, known as the Windy City, offers a vibrant and diverse experience for tourists. With a rich history, stunning architecture, world-class museums, and a thriving food and music scene, Chicago has something for everyone. Notable landmarks include the iconic Willis Tower (formerly known as the Sears Tower), Millennium Park with its famous Bean sculpture, Navy Pier, and the Art Institute of Chicago, home to masterpieces like Grant Woods American Gothic and Georges Seurats A Sunday on La Grande Jatte.

Why is choosing vacation rentals in Chicago better than staying in a hotel?

Space and comfort: Vacation rentals offer more space than a typical hotel room, providing separate living areas, bedrooms, and kitchens, making it perfect for families or larger groups.

Authentic experience: Staying in a vacation rental allows you to immerse yourself in the local culture and community, providing a more authentic experience of living like a Chicago local.

Price and value: Vacation rentals can often be more cost-effective than staying in a hotel, especially for longer stays, as they offer amenities like fully equipped kitchens, washing machines, and complimentary Wi-Fi.

Privacy and flexibility: With your own rental, you have the freedom to come and go as you please, without adhering to hotel schedules or common areas.

Neighborhood immersion: Chicago is a city of diverse neighborhoods, each with its own charm and character. By choosing a vacation rental, you can select one in your preferred neighborhood, allowing you to explore and experience the local scene.

Vacation Rentals in Chicago

Apartments:

Chicago Chic: Stylish, modern apartment in the heart of downtown, with stunning city views and close proximity to popular attractions.

Cozy Lincoln Park Retreat: Located in the trendy Lincoln Park neighborhood, this apartment offers comfort and convenience, with easy access to parks, restaurants, and shopping.

Lakefront Luxury: Upscale apartment overlooking Lake Michigan, offering breathtaking views and access to nearby beaches and waterfront activities.

House:

Classic Brownstone: A beautifully restored historic brownstone home in the historic Gold Coast neighborhood, offering elegance and charm, with easy access to the Magnificent Mile and lakefront.

Family-Friendly Retreat: Spacious house with multiple bedrooms and a backyard, perfect for families, located in the family-friendly neighborhood of Wicker Park.

Townhouse:

Modern Townhouse: Contemporary townhouse in River North, known for its art galleries, nightlife, and dining options, providing a comfortable and stylish stay.

Historic Charm: A beautifully preserved townhouse in the Old Town neighborhood, offering a glimpse into Chicagos rich history, with easy access to Lincoln Park and the zoo.

Luxury Rentals:

The Penthouse: Luxurious penthouse apartment with panoramic views of the city skyline, located in the prestigious Streeterville neighborhood, offering high-end amenities and a prime location.

Lakefront Mansion: A grand mansion overlooking Lake Michigan, complete with a private pool, jacuzzi, and rooftop terrace, providing the ultimate luxury experience.

Homes with a Pool:

Lincoln Park Oasis: Spacious home with a private pool and backyard, located in Lincoln Park, perfect for relaxing after a day of exploring the city.

Lakefront Retreat: Stunning lakefront home with an outdoor pool and direct access to the beach, offering a luxurious and serene getaway.

Waterfront/Near Beachfront:

Lakeview Paradise: A cozy apartment with lake views and easy access to the lakefront trail and popular beaches, located in the vibrant Lakeview neighborhood.

Beachside Bungalow: A charming bungalow just steps away from the beach, nestled in the Edgewater neighborhood, known for its stunning views and beach activities.

Show moreLess
Guest reviews of hotels in Chicago