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Chicago Vacation Rentals

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Featured Vacation Homes in Chicago

Essence Suite W/spa Bath
South Holland, IL
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4/5Very Good! (5 reviews)
Great property, Great property owner

"My family had a great time. The children enjoyed being together. Enough space for everyone. Property owner was the best."…"

Reviewed on Nov. 12, 2020

Essence Suite W/spa Bath
Cambridge Estates
4 out of 5
Cambridge Court, Darien, IL
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Situated in Darien, this holiday home is 2.3 mi (3.8 km) from National Shrine of St. Therese and 3 mi (4.9 km) from Promenade Bolingbrook. Willowbrook Community ...

Cambridge Estates
Quaint Bungalow, Near Great Lakes Naval Base
628 North Prairie Avenue, Mundelein, IL
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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 Lake County ...

4.9/5Exceptional! (22 reviews)
Enjoyed our stay

"the house was in a great location and very nice for our family."…"

Reviewed on Aug. 10, 2020

Quaint Bungalow, Near Great Lakes Naval Base
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Stunning Lake Views, Relaxing Getaway on the Chain O'lakes
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Situated on a lake, this holiday home is within 9 miles (15 km) of Volo Bog State Natural Area, Wilmot Mountain and Volo Auto Museum. Millennium Trail Trailhead ...

4.8/5Exceptional! (21 reviews)
Great property very clean had a great time.

"This was a great experience i had alot of fun with friends thanks for having us."…"

Reviewed on Oct. 18, 2020

Stunning Lake Views, Relaxing Getaway on the Chain O'lakes
Fox Lake Semi Secluded Waterfront! 3 Properties!
The price is CA $208 per night from Dec 2 to Dec 3

Situated on the waterfront, this holiday home is within 9 miles (15 km) of Volo Bog State Natural Area, Wilmot Mountain and Volo Auto Museum. McCullom Lake and ...

4.8/5Exceptional! (11 reviews)
Highly recommended

"Everything for out trip came together quite easily, mostly because of the property and it's owner. Michelle was quick to respond to our questions, and the check in/out processes were fast. We had four people sharing the cabin and there was more than enough room inside. The yard was the best part ..."…"

Reviewed on Sep. 30, 2020

Fox Lake Semi Secluded Waterfront! 3 Properties!
1821
3.5 out of 5
1821 North Hampton Drive, Highlands Rese, Berwyn, IL
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Situated in Berwyn, this holiday home is within 6 miles (10 km) of Frank Lloyd Wright Home and Studio, Brookfield Zoo and Douglas Park. United Center and University ...

1821
Historic and Charming House on Large Wooded Lot, 10 Minute Walk to Chicago Train
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Situated in Homewood, this holiday home is 0.4 mi (0.7 km) from Ravisloe Country Club and within 3 miles (5 km) of Oak Hill Park and Advocate South Suburban ...

Historic and Charming House on Large Wooded Lot, 10 Minute Walk to Chicago Train
Columbia Bay Compound, Two Homes Great Groups And Families On The Chain'o'lakes!
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Situated on the waterfront, this holiday home is within 12 miles (20 km) of Vista Medical Center - Lindenhurst, Wilmot Mountain and Lake Miltmore Beach. Volo ...

3.5/5Good! (2 reviews)
Misleading

"We had a great time at the property, though the listing is extremely misleading. Far too expensive for a dirty (cob webs, many spiders, dirty toilets), unkept (mantle points down instead of straight, paintings on the wall were crooked, extremely dusty, old bedding) and stinky (musty, stuffy) experience. ..."…"

Reviewed on Oct. 15, 2018

Columbia Bay Compound, Two Homes Great Groups And Families On The Chain'o'lakes!
Sunset Cottage on Pistakee Lake
503 Pistakee Pkwy, Fox Lake, IL
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Situated in Fox Lake, this holiday home is within 9 miles (15 km) of Volo Bog State Natural Area, Wilmot Mountain and Volo Auto Museum. Millennium Trail Trailhead ...

4.8/5Exceptional! (32 reviews)
Right on the water

"Perfect location for summer"…"

Reviewed on Nov. 30, 2020

Sunset Cottage on Pistakee Lake
Private Retreat Style Lake House With Amazing Views for up to 12!
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Located on the waterfront, this family-friendly holiday home is within 6 mi (10 km) of Volo Bog State Natural Area, Petersen Park Beach, and McHenry Shores Beach ...

5/5Exceptional! (15 reviews)
Fabulous property

"We had a terrific long weekend with kids and grandkids. Enjoyed by all. The property is a one of a kind. The views are incredible. We loved it."…"

Reviewed on Oct. 4, 2020

Private Retreat Style Lake House With Amazing Views for up to 12!
Enjoy Your Vacation On Lake Pistakee Of The Chain
503 Pistakee Pkwy, Unit 3, Fox Lake, IL
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Situated on a lake, this holiday home is within 9 miles (15 km) of Volo Bog State Natural Area, Wilmot Mountain and Volo Auto Museum. Millennium Trail Trailhead ...

4.8/5Exceptional! (14 reviews)
Great stay

"Great place to stay on the lake and we had a great time!"…"

Reviewed on Oct. 7, 2020

Enjoy Your Vacation On Lake Pistakee Of The Chain
Sanitizedroomy Retreatfree Wifi & Free Parkingnear Downtwn Chicago
The price is CA $181 per night from Dec 2 to Dec 3

This family-friendly Lansing holiday home is within 1 mi (2 km) of Lansing Square Shopping Center and Lan-Oak Park. River Oaks Center and Theatre at the Center ...

4.8/5Exceptional! (5 reviews)
Review

"Definitely would recommend, this is a quaint space with easy and secure check-in/checkout process. Covid-19 protocol were followed."…"

Reviewed on Nov. 16, 2020

Sanitizedroomy Retreatfree Wifi & Free Parkingnear Downtwn Chicago
Hensleys Cornerstone Lakehouse
149 North Ave, Wauconda, IL
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Situated in Wauconda, this holiday home is within a 15-minute walk of Cook Memorial Park and Wauconda Village Hall. Lake County Discovery Museum and Fox River ...

4.8/5Exceptional! (4 reviews)
Beautiful Home

"We so enjoyed our stay! It was the perfect location for a team retreat and training and Crystal was so great to communicate with us and make sure we were taken care of during our stay!"…"

Reviewed on Nov. 18, 2020

Hensleys Cornerstone Lakehouse
Beautiful Spacious Escape On The Chain O'lakes
503 Pistakee Pkwy, Unit 1, Fox Lake, IL
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Situated on the waterfront, this romantic holiday home is within 9 miles (15 km) of Volo Bog State Natural Area, Wilmot Mountain and Volo Auto Museum. Millennium ...

4.8/5Exceptional! (22 reviews)
Great Retreat!

"The property is really fun and the lake is so beautiful. We had a great wonderful down by the fire pit, exploring near-by nature preserves, and relaxing all throughout the house. It was a very nice weekend, thank you!"…"

Reviewed on Nov. 10, 2020

Beautiful Spacious Escape On The Chain O'lakes
New!! The Jewell, A Luxury Accommodation
15942 Hamlin Ave, Markham, IL
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Situated in Markham, this holiday home is within 3 miles (5 km) of Advocate South Suburban Hospital, Advocate South Suburban Hospital and Oak Hill Park. Ingalls ...

New!! The Jewell, A Luxury Accommodation
Awesome Fully Furnished 2 Bedroom Townhome With Secluded Wooded Area
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Situated in Aurora, this holiday home is 1.9 mi (3 km) from Copley Memorial Hospital and 2.4 mi (3.8 km) from Rush-Copley Medical Center. Hollywood Casino Aurora ...

Awesome Fully Furnished 2 Bedroom Townhome With Secluded Wooded Area
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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 property types in Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
127 West Huron, at LaSalle, Chicago, IL
The price is CA $92 per night from Jan 1 to Jan 2
4.3/5Excellent! (1,594 reviews)

"Love everything! The hotel was nice and staff was generous."…"

Reviewed on Nov. 24, 2020

The Godfrey Hotel Chicago
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive, Chicago, IL
The price is CA $149 per night from Dec 2 to Dec 3
4.6/5Wonderful! (2,589 reviews)

"Great location. Walking distance to many Chicago sites! Beautiful river/city view from our room. Check-in and checkout were quick and can be contactless. The rooms are also very clean! Going to be staying here next time I’m in Chicago :)"…"

Reviewed on Nov. 24, 2020

LondonHouse Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile, previously Dana Hotel

Eurostars Magnificent Mile, previously Dana Hotel

4 out of 5
660 North State Street, Chicago, IL
The price is CA $113 per night from Dec 6 to Dec 7
4.5/5Wonderful! (1,766 reviews)

"Great Hotel I would stay again any day. The room had a great view."…"

Reviewed on Nov. 29, 2020

Eurostars Magnificent Mile, previously Dana 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.

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