Chicago Vacation Rentals - HolidayHomes base64Hash Chicago Vacation Rentals - HolidayHomes

Chicago Vacation Rentals

Browse 5,600 available vacation homes and compared across 10 trusted partners

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Top-Rated Vacation rentals in Chicago

Book the highest-rated Chicago vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Motel River North

Ohio House Motel

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Motel River North

Ohio House Motel

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Motel River North

Ohio House Motel

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Bed and breakfast Old Town

The Sono Chicago

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Bed and breakfast Old Town

The Sono Chicago

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Bed and breakfast Old Town

The Sono Chicago

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Bed and breakfast Old Town

The Sono Chicago

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Bed and breakfast Magnolia Glen

House 5863 - Chicago Bed and Breakfast

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Bed and breakfast Magnolia Glen

House 5863 - Chicago Bed and Breakfast

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Bed and breakfast Magnolia Glen

House 5863 - Chicago Bed and Breakfast

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Bed and breakfast Bucktown

Ray's Bucktown B&B

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Bed and breakfast Bucktown

Ray's Bucktown B&B

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Bed and breakfast Bucktown

Ray's Bucktown B&B

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Bed and breakfast Wicker Park

Wicker Park Inn

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Bed and breakfast Wicker Park

Wicker Park Inn

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Top 15 most Recommended Vacation Rentals in Chicago

Discover your ideal Chicago vacation rental with real-time comparisons of 5,600 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Bed & breakfast with yard, barbecue & terrace | Perfect for remote work

Sheffield & DePaul, Chicago, Illinois, United States
Cozy bed and breakfast rental in Sheffield Neighbors accommodating 6 guests with a charming fireplace for a warm atmosphere.
from $404
per night
(122)
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Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with garden & patio | Suitable for remote work

Bucktown, Chicago, Illinois, United States
Cozy Bed and breakfast rental in Bucktown accommodates 2 guests and features a kitchen for convenient meal preparation.
from $198
per night
(412)
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Bed and breakfast with terrace, barbecue & yard

Sheffield & DePaul, Chicago, Illinois, United States
This cozy bed and breakfast rental in Sheffield Neighbors accommodates 5 guests and features a charming fireplace for a warm ambiance.
from $337
per night
(122)
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Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented spacious B&B with patio & yard | Good for workation | Pets allowed

Bucktown, Chicago, Illinois, United States
Charming bed and breakfast rental in Bucktown for 2 guests featuring a cozy kitchen and pets allowed for a welcoming stay.
from $197
per night
(412)
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Bed and breakfast Fulton Market
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Fulton Market, Chicago, Illinois, United States
Charming bed and breakfast rental in West Loop accommodates 2 guests and offers a free breakfast to start your day.
from $261
per night
(211)
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Motel Rogers Park
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

Rogers Park, Chicago, Illinois, United States
This cozy motel in Rogers Park offers comfortable accommodations for 2 guests and convenient parking for all visitors.
from $127
per night
(38)
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Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with garden

Wicker Park, Chicago, Illinois, United States
Charming bed and breakfast rental in Wicker Park accommodating 2 guests with a lovely yard for relaxation.
from $289
per night
(279)
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Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with patio, barbeque & yard | Garden view | Good for workation

Magnolia Glen, Chicago, Illinois, United States
Charming bed and breakfast rental in Magnolia Glen accommodates 2 guests and features a cozy kitchen and complimentary breakfast.
from $239
per night
(514)
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Motel Washington Heights
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel for 2 persons

Washington Heights, Chicago, Illinois, United States
This motel in Washington Heights offers cozy accommodations for 2 guests and features convenient parking for all visitors.
from $86
per night
(437)
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