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Chicago Holiday Rentals

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Holiday Rentals in Chicago

Cimarron 1 Bedroom Cabin

Cimarron 1 Bedroom Cabin

3 out of 5
171 Hickory Bend, Hickory Hills, IL
Situated in Hickory Hills, this cabin is 2.8 mi (4.5 km) from Chicago Ridge Shopping Mall and within 6 miles (10 km) of SeatGeek Stadium and Water's Edge Golf ...
Cimarron 1 Bedroom Cabin
Sierra 1 Bedroom Cabin

Sierra 1 Bedroom Cabin

3 out of 5
695 Hickory Bend Road, Hickory Hills, IL
Situated in Hickory Hills, this cabin is 2.8 mi (4.5 km) from Chicago Ridge Shopping Mall and within 6 miles (10 km) of SeatGeek Stadium and Water's Edge Golf ...
Sierra 1 Bedroom Cabin
The Hemingway An Explorers Retreat

The Hemingway An Explorers Retreat

308 N East Ave, 2, Oak Park, IL
The price is NZ$433 per night from 23 Apr. to 24 Apr.
Located in the heart of Oak Park, this condo is 0.7 mi (1.2 km) from Frank Lloyd Wright Home and Studio and within 6 miles (10 km) of Humboldt Park and Garfield ...
3/5 (1 review)
Mostly Lovely Apartment in Nice Neighborhood
"Listing does not mention STAIRS anywhere. None of us has physical limitations but the only way up to the apartment is dimly lit and there are sharp turns where a fall is possible (I did and yes, I know how to use stairs; I haven't fallen down stairs since I was a child). Too many left-behind items ..."

Reviewed on 17 Apr. 2021

The Hemingway An Explorers Retreat
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Expansive Farmhouse Estate - Stunning!

Expansive Farmhouse Estate - Stunning!

2S477 Madison St, Warrenville, IL
This family-friendly Warrenville holiday home is within 2 mi (3 km) of Blackwell Forest Preserve and Arrowhead Golf Club. DuPage Children's Museum and Cosley ...
5/5Exceptional! (1 review)
Quick getaway
"Quick & easy communication. Our family loved the beautiful and spacious house, took lots of walks, shopped, visited Chicago etc. Good memories and not too far from home!"

Reviewed on 2 Apr. 2021

Expansive Farmhouse Estate - Stunning!
Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

2.5 out of 5
55 E Washington St., Chicago, IL
Located in The Loop, this aparthotel is steps away from Chicago Cultural Center, Grant Park and Millennium Park. Chicago Theatre and Michigan Avenue are also ...
3.1/5 (1,265 reviews)
"I did not stay there because I was told by security management shout down the building which my family I was able too check in our room, he would not allow us to speak with any one else about the matter (ALL OVER A FACE MASK) ruined my night.. I try calling front desk no one would answer I WOULD ..."

Reviewed on 22 Jun. 2020

Pittsfield Apartments + Suites
Niche Accommodation in Chicago Suburb - Elm Room

Niche Accommodation in Chicago Suburb - Elm Room

437 S Craig Pl, Lombard, IL
Situated in Lombard, this holiday home is 0.8 mi (1.3 km) from Lilacia Park and within 6 miles (10 km) of Oakbrook Center Mall and Wheaton College. Odeum Sports ...
Niche Accommodation in Chicago Suburb - Elm Room
Niche Accommodation in Chicago Suburb - Oak Room

Niche Accommodation in Chicago Suburb - Oak Room

437 S Craig Pl, Lombard, IL
Situated in Lombard, this holiday home is 0.8 mi (1.3 km) from Lilacia Park and within 6 miles (10 km) of Oakbrook Center Mall and Wheaton College. Odeum Sports ...
Niche Accommodation in Chicago Suburb - Oak Room
Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

628 North Prairie Avenue, Mundelein, IL
Situated in Mundelein, this holiday home is 2.7 mi (4.3 km) from Lakeview Beach and Dock and within 6 miles (10 km) of MainStreet Libertyville and Advocate Condell ...
4.9/5Exceptional! (23 reviews)
Spring Break
"Rented this place to enjoy our spring break. The owner gave specific and simple instructions and everything was perfect! Would recommend to everyone! Right in the heart of all kinds of activities"

Reviewed on 11 Apr. 2021

Quaint Bungalow, near Great Lakes Naval Base
Steps From Wrigley Field 3 Bedroom 2 Bathroom Apartment Sleeps 7 Allstar Suite

Steps From Wrigley Field 3 Bedroom 2 Bathroom Apartment Sleeps 7 Allstar Suite

3619 N Sheffield Ave, Chicago, IL
Located in Lakeview, this condo is within a 15-minute walk of Wrigley Field and Vic Theatre. Briar Street Theatre and DePaul University-Lincoln Park are also ...
4.3/5Excellent! (7 reviews)
Wrigley
"Was quick and easy to get in and settled. The owner very accommodating for our last minute rental. A few more essentials would have been nice ( wine bottle opener). There are no services during the stay which is totally fine, but as there is a specific service fee added to the rental, The TO DO list ..."

Reviewed on 25 Oct. 2019

Steps From Wrigley Field 3 Bedroom 2 Bathroom Apartment Sleeps 7 Allstar Suite
New! Updated Escape w/ Deck+yard Near Northwestern

New! Updated Escape w/ Deck+yard Near Northwestern

1538 Fowler Avenue, Evanston, IL
Situated in Evanston, this apartment building is 2.1 mi (3.4 km) from Northwestern University and 3 mi (4.8 km) from Baha'i House of Worship. Loyola University ...
New! Updated Escape w/ Deck+yard Near Northwestern
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chicago you may be interested in

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is NZ$161 per night from 19 Apr. to 20 Apr.
River Hotel
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is NZ$278 per night from 26 Apr. to 27 Apr.
LondonHouse Chicago, Curio Collection by Hilton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.