The 10 best vacation homes in Chicago, US | Booking.com
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Vacation Homes in Chicago

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The best vacation homes in Chicago

Check out our selection of great vacation homes in Chicago

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Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

K
Krystyna
From
Canada
Located reasonably close to downtown.Kept clean and had a homey feeling.located in the very nice old neighbourhood..Our car was parked right in front of our porch.The porch was the best.The breakfasts on the porch in the shade of the old tree. Thank you Andrea. We will come back.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Location 10.0
Price from
$450
1 night, 2 adults
Check availability

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S
Strand
From
United States
This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 29 reviews
Location 9.8
Price from
$419
1 night, 2 adults
Check availability

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Location 10.0
Price from
$499
1 night, 2 adults
Check availability

Lakefront Rooftop Parking

Chicago

Providing a garden, Lakefront Rooftop Parking features accommodations in Chicago. This beachfront property offers access to a balcony, free private parking, and free Wifi.

D
Demetris
From
United States
Very nice, the owner was very helpful and on time with my needs, felt like home❤️
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 6 reviews
Location 9.0
Price from
$319.50
1 night, 2 adults
Check availability

A Home Away from Home!

Chicago

A Home Away from Home! is located in Chicago, just 4.7 miles from Museum of Science and Industry - Chicago and 9.4 miles from Guaranteed Rate Field.

U
Usman
From
United States
5 stars Wonderful Stay! I had an amazing experience staying at this Airbnb! The home was exactly as described clean, cozy, and thoughtfully decorated. The host was incredibly responsive and made the check-in process super smooth. The neighborhood was quiet and safe, with great local restaurants and shops nearby. I especially appreciated the little touches, like fresh towels, snacks, and local recommendations
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 7 reviews
Location 8.4
Price from
$106.70
1 night, 2 adults
Check availability

Home Away From Home

Skokie (Near Chicago)

Home Away From Home is located in Skokie, just 5.4 miles from Loyola University Chicago and 7.9 miles from Wrigley Field. This property offers access to a patio, free private parking, and free Wifi.

A
Alexandra
From
United States
The house was cozy clean and comfortable the host was absolutely phenomenal and made the stay a great experience
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 5 reviews
Location 9.5
Price from
$174.30
1 night, 2 adults
Check availability

The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

K
Kam
From
United States
Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 134 reviews
Location 9.2
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Chicago Treasure 4 Bed Getaway

West Town, Chicago

Chicago Treasure 4 Bed Getaway offers accommodations in Chicago, 2.1 miles from 360 Chicago and 2.1 miles from Chicago Museum of Contemporary Art.

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 6 reviews
Location 9.1
Check availability

The Logandale: HUGE Mid-Century Home, sleeps 15

Chicago

The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.8 miles from Lincoln Park Zoo and 6 miles from United Center.

L
Lisa
From
United States
Excellent location! The house was comfy and very clean, loved the coffee bar. Danny the host was awesome!
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 5 reviews
Location 9.5
Check availability

Beautifully Renovated House 10 mins from Downtown

Bronzeville, Chicago

Beautifully Renovated House 10 mins from Downtown offers accommodations in Chicago, 1.5 miles from Oakwood Beach and 1.7 miles from Guaranteed Rate Field.

N
Nermin
From
United States
Excellent location, beautiful, clean and spacious house with all amenities needed. Fantastic communication and friendly service, would love to stay here again.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews
Location 9.1
Check availability
All vacation homes in Chicago

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Chicago and surrounding area in the past month

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Great access to the city center. Check these vacation homes in Chicago and nearby

  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage is located in Chicago, just a 17-minute walk from Willis Tower and 1.4 miles from CIBC Theatre.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 5 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 5 reviews

    A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

  • Located in Chicago, this holiday home is 0.7 mi from Lincoln Park Zoo and Downtown Chicago. Offering free private parking, the holiday home is 0.9 mi from 360 Chicago.

  • Scored out of 10, guest rating 8.3
    Very Good - What previous guests thought, 3 reviews

    5 Bedroom Huge House in Best Location Parking Fireplace Back Yard offers accommodations in Chicago, a 18-minute walk from North Avenue Beach and 1.4 miles from Water Tower Chicago.

  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 1 review

    Old Town 3bd 3ba Coach House, Garage Parking Incl is located in Chicago, just 1.6 miles from Water Tower Chicago and 1.6 miles from 360 Chicago.

  • Just a 13-minute walk from North Avenue Beach and 0.7 miles from Lincoln Park Zoo, Top 1 Rated 4BR Lincoln Park House - King Bed features accommodations in Chicago, with a fitness center and a garden.

Save money on vacation homes in Chicago and nearby – budget options available

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Hotels near Union Station

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