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Our top choices for Chicago vacation homes

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ¥24,678
¥47,266 total
includes taxes & fees
Jan 28 - Jan 29
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Near Lake and Museum • Pool Table • Game Area

Near Lake and Museum • Pool Table • Game Area
2.0 star property
South Shore
The price is ¥5,378
¥71,155 total
includes taxes & fees
Jan 26 - Jan 27
Near Lake and Museum • Pool Table • Game Area

Newly remodeled Near Lake 4BR Hot Tub Navy Family home

Newly remodeled Near Lake 4BR Hot Tub Navy Family home
2.0 star property
Gages Lake
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is ¥17,401
¥84,618 total
includes taxes & fees
Jan 27 - Jan 28
Newly remodeled Near Lake 4BR Hot Tub Navy Family home

Walk to Wrigley Field! Townhouse w/ Pool Table

Walk to Wrigley Field! Townhouse w/ Pool Table
2.0 star property
Lakeview
The price is ¥19,457
¥96,280 total
includes taxes & fees
Jan 25 - Jan 26
Walk to Wrigley Field! Townhouse w/ Pool Table

Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen
2.0 star property
Humboldt Park
The price is ¥20,760
¥77,072 total
includes taxes & fees
Jan 26 - Jan 27
Gated Family Home w/ Chef’s Kitchen

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
La Grange Highlands
10.0 out of 10, Exceptional, (4 reviews)
"very professional hosts and warm accommodations thank you!"
United States
Shawn T.
The price is ¥13,478
¥40,187 total
includes taxes & fees
Jan 25 - Jan 26
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (33 reviews)
"great stay"
United States
matt R.
The price is ¥9,205
¥30,459 total
includes taxes & fees
Jan 27 - Jan 28
A quiet stay while you are away

Cozy Estate in charming Willow Springs 20 minutes from Downtown and Beaches

Cozy Estate in charming Willow Springs 20 minutes from Downtown and Beaches
2.0 star property
Willow Springs
10.0 out of 10, Exceptional, (1 review)
"Host was great at communicating throughout the process. House was perfect. Great yard for the dogs and looks to be recently updated and very clean. Wasn’t a fan of being forced into the insurance or they take a big deposit when you book but don’t know if that is this listing or a VRBO thing. Still besides that it was perfect. Would definitely stay again. "
United States
Raymond H.
Cozy Estate in charming Willow Springs 20 minutes from Downtown and Beaches

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
Portage Park
The price is ¥23,729
¥138,111 total
includes taxes & fees
Jan 25 - Jan 26
Sleeps 18 • 8BR • Game Room • Gym • Theater

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ¥16,942
¥44,443 total
includes taxes & fees
Jan 25 - Jan 26
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames
North Chicago
9.8 out of 10, Exceptional, (19 reviews)
"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "
United States
Thomas D.
The price is ¥19,809
¥82,983 total
includes taxes & fees
Jan 26 - Jan 27
North Chi retreatNavySaunaTiki BarGames

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (19 reviews)
"Great place Great location "
United States
Josh W.
The price is ¥24,084
¥64,350 total
includes taxes & fees
Jan 25 - Jan 26
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (76 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is ¥15,518
¥30,696 total
includes taxes & fees
Jan 27 - Jan 28
Master qtr close to nature & easy urban facilities

Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector
2.0 star property
Waukegan
8.8 out of 10, Excellent, (3 reviews)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is ¥19,774
¥42,919 total
includes taxes & fees
Jan 25 - Jan 26
Home -2 bedroom, 4k projector

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (55 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is ¥25,310
¥53,417 total
includes taxes & fees
Feb 10 - Feb 11
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Charming 5BD 2BA with spacious yard near O'hare

Charming 5BD 2BA with spacious yard near O'hare
2.0 star property
Melrose Park
The price is ¥35,593
¥88,693 total
includes taxes & fees
Feb 1 - Feb 2
Charming 5BD 2BA with spacious yard near O'hare

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is ¥26,937
¥79,915 total
includes taxes & fees
Jan 26 - Jan 27
Vintage Urban Retreat

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
2.0 star property
Homewood
The price is ¥23,137
¥63,415 total
includes taxes & fees
Feb 18 - Feb 19
Modern Stylish Comfort Near Casino and Hwy

Beautiful House in Carol Stream near Downtown Chicago

Beautiful House in Carol Stream near Downtown Chicago
Carol Stream
9.6 out of 10, Exceptional, (4 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is ¥20,109
¥80,659 total
includes taxes & fees
Jan 25 - Jan 26
Beautiful House in Carol Stream near Downtown Chicago

New! 10-min to Downtown

New! 10-min to Downtown
2.0 star property
Oak Park
The price is ¥42,711
¥97,242 total
includes taxes & fees
Jan 26 - Jan 27
New! 10-min to Downtown
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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Top Chicago Hotel Reviews

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Chicago Vacation Homes information

Number of reviews
224
Accommodation
822 Vacation Homes
Lowest Price
¥30,459
Highest Price
¥138,111