Find and Book Top Rated Vacation rentals in Chicago

Search among 30 available vacation rentals in Chicago from 50+ providers

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8 adults
3 bedrooms
5 beds
MapView on map4.9 mi from City Center500 yd from Viaduct Center
From   US$ 164 /nightSelect
10 adults
3 bedrooms
3 beds
MapView on map2.1 mi from City Center1.1 mi from Michigan Avenue
From   US$ 699 /nightSelect
Great21 reviews
5.6 mi from City Center400 yd from
From   US$ 41 /nightSelect
Perfect1 review
3.8 mi from City Center200 yd from
From   US$ 107 /nightSelect
Great1 review
3.8 mi from City Center400 yd from
From   US$ 202 /nightSelect
Very good1 review
3.5 mi from City Center900 yd from
From   US$ 133 /nightSelect
Very good1 review
4.2 mi from City Center300 yd from
From   US$ 376 /nightSelect
9.6 mi from City Center1100 yd from South Shore Hospital
From   US$ 233 /nightSelect
Great16 reviews
2.4 mi from City Center400 yd from
From   US$ 119 /nightSelect
Great14 reviews
4.8 mi from City Center700 yd from Wrigley Field
From   US$ 550 /nightSelect
Very good1 review
5.0 mi from City Center900 yd from
From   US$ 268 /nightSelect
1.7 mi from City Center800 yd from McCormick Place
From   US$ 958 /nightSelect
1.5 mi from City Center500 yd from Michigan Avenue
From   US$ 992 /nightSelect
8.7 mi from City Center300 yd from Indo-American Center
From   US$ 127 /nightSelect
Perfect1 review
3.2 mi from City Center400 yd from Lincoln Park Hospital
From   US$ 169 /nightSelect
6.2 mi from City Center700 yd from Applied Research Technical
From   US$ 81 /nightSelect
4.6 mi from City Center1700 yd from Wrigley Field
From   US$ 165 /nightSelect
1.6 mi from City Center800 yd from Michigan Avenue
From   US$ 765 /nightSelect
6.0 mi from City Center800 yd from
From   US$ 123 /nightSelect
1.5 mi from City Center700 yd from Michigan Avenue
From   US$ 385 /nightSelect
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Best vacation rentals in Chicago

Why visit?

Chicago, known as the Windy City, offers a blend of culture, arts, and breathtaking architecture. Visitors are drawn to iconic landmarks such as the Willis Tower (formerly Sears Tower), the Art Institute of Chicago, Millennium Park with its famed Cloud Gate sculpture, and the vibrant Navy Pier. The city also boasts a rich culinary scene, world-class museums, and stunning lakefront views.

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

Space: Vacation rentals offer more space and privacy, ideal for families or large groups.

Local experience: Staying in a vacation rental allows you to live like a local, experiencing the authentic Chicago lifestyle.

Cost-effective: You can often find vacation rentals at a lower cost than hotels, especially for longer stays.

Amenities: Many vacation rentals come equipped with full kitchens and laundry facilities, providing convenience and cost savings.

Unique options: From charming brownstones to modern condos, vacation rentals offer a diverse array of accommodations to suit different preferences.

Vacation rentals in Chicago


Luxurious Downtown Apartment: Located in the heart of downtown, this modern apartment offers stunning city views and close proximity to attractions.

Cozy River North Loft: Perfect for solo travelers or couples, this chic loft boasts a prime location in the trendy River North neighborhood.

Lakefront Retreat: Enjoy panoramic views of Lake Michigan from this stylish apartment on the waterfront.


Historic Greystone Home: Experience Chicagos history in this beautifully restored Greystone house, featuring elegant interiors and a private garden.

Spacious Family Home: Ideal for families, this charming house in a residential neighborhood offers comfort and tranquility.


Modern Townhouse in Lincoln Park: Nestled in the upscale Lincoln Park area, this contemporary townhouse provides easy access to parks and restaurants.

Riverfront Townhouse: Embrace the riverside lifestyle at this townhouse, offering serene views and a peaceful atmosphere.

Luxury rentals:

Magnificent Mile Penthouse: Indulge in luxury at this upscale penthouse located on the iconic Magnificent Mile, featuring lavish amenities and breathtaking skyline views.

Art Deco Style Residence: Step back in time at this Art Deco residence, offering a unique blend of vintage charm and modern comforts.

Homes with a pool:

Gold Coast Oasis: Relax in a private pool oasis at this exclusive Gold Coast residence, just steps away from the citys finest shopping and dining.

Lincoln Park Retreat: Escape to a tranquil haven with a beautiful backyard pool, perfect for enjoying sunny days in the heart of Lincoln Park.

Waterfront / Near beachfront:

Lakefront Condo: Unwind by the lake at this stylish condo, boasting a prime location near Chicagos famous Oak Street Beach.

Beachfront Bungalow: Experience the ultimate beach getaway at this charming bungalow, offering direct access to the picturesque North Avenue Beach.

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