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Top 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
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
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
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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
3 Bedrooms 3 King Beds Ideal Refuge During the Crisis

3 Bedrooms 3 King Beds Ideal Refuge During the Crisis

311 W Park Ave, Apt. #1, Libertyville, IL
Situated in Libertyville, this apartment building is within 1 mile (2 km) of MainStreet Libertyville and Advocate Condell Child Day Center. Lambs Farm and Independence ...
5/5Exceptional! (4 reviews)
Excellent place
"We rented the apartment while we in the area for my son's graduation from Navy Bootcamp. The apartment was super cute and clean and four of us comfortably stayed there. We were able to have his Aunt and Uncle come visit one evening as well and there was plenty of room for the six of us to sit around ..."

Reviewed on 12 Feb 2020

3 Bedrooms 3 King Beds Ideal Refuge During the Crisis
OP7 Downtown 2BR Spacious Living & Kitchen, King Beds

OP7 Downtown 2BR Spacious Living & Kitchen, King Beds

Apt 805 922 North Boulevard, Oak Park, IL
Situated in Oak Park, this apartment building is 0.6 mi (1 km) from Frank Lloyd Wright Home and Studio and within 6 miles (10 km) of Brookfield Zoo and Garfield ...
OP7 Downtown 2BR Spacious Living & Kitchen, King Beds
High-end Apartment in the Heart of River North

High-end Apartment in the Heart of River North

1 W Superior St, 3502, Chicago, IL
Located in River North, this apartment building is steps away from Holy Name Cathedral and State Street. Water Tower Place and John Hancock Center are also within ...
4.8/5Exceptional! (18 reviews)
Great location bad furniture
"We loved the location of this unit, the quietness, and the great building amenities. We would not rent the unit again because of the poor quality of the furniture, especially the couch. The couch is uncomfortable, unstable, very low to the ground, and feels like it is falling apart. The beds are ..."

Reviewed on 7 Mar 2020

High-end Apartment in the Heart of River North
OP5 2BR Close to Everything 20min Train to Chicago

OP5 2BR Close to Everything 20min Train to Chicago

208 922 North Boulevard, Oak Park, IL
Situated in Oak Park, this apartment building is 0.6 mi (1 km) from Frank Lloyd Wright Home and Studio and within 6 miles (10 km) of Brookfield Zoo and Garfield ...
OP5 2BR Close to Everything 20min Train to Chicago
HP2 Highland Park Minimalist Studio Unit - Near Metra!

HP2 Highland Park Minimalist Studio Unit - Near Metra!

Apt H 716 Central Avenue, Highland Park, IL
Situated in Highland Park, this apartment building is within 1 mile (2 km) of Highland Park Ambulatory Care Center, Park Avenue Boating-Fishing Beach and Lake ...
HP2 Highland Park Minimalist Studio Unit - Near Metra!
OP8 2BR King Beds,big Living & Dining for Family/group

OP8 2BR King Beds,big Living & Dining for Family/group

305 922 North Boulevard, Oak Park, IL
Situated in Oak Park, this apartment building is 0.6 mi (1 km) from Frank Lloyd Wright Home and Studio and within 6 miles (10 km) of Brookfield Zoo and Garfield ...
OP8 2BR King Beds,big Living & Dining for Family/group
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Other types of properties in Chicago you may be interested in

The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is £66 per night from 17 May to 17 May
The Whitehall Hotel
Loews Chicago Hotel

Loews Chicago Hotel

4.5 out of 5
455 North Park Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is £141 per night from 24 May to 24 May
Loews Chicago Hotel
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.