Holiday Homes in Central Chicago

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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Holiday Homes in Central Chicago

Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
2.0 star property
10.0 out of 10, Exceptional, (11)
"Very clean in a safe neighborhood. I would stay here again"
United States
Charles W.
The price is AU$310
includes taxes & fees
20 Oct - 21 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior
A quiet stay while you are away
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
United States
Karigan H.
The price is AU$299
includes taxes & fees
29 Oct - 30 Oct
A quiet stay while you are away
Exterior
Coziest estate home 20 minutes to downtown
Coziest estate home 20 minutes to downtown
8.8 out of 10, Excellent, (13)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
The price is AU$624
includes taxes & fees
21 Oct - 22 Oct
Coziest estate home 20 minutes to downtown
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.6 out of 10, Exceptional, (52)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is AU$518
includes taxes & fees
21 Oct - 22 Oct
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (1)
"Very quiet and private and cl9se to alot of things "
United States
Kenneth W.
The price is AU$412
includes taxes & fees
22 Oct - 23 Oct
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fridge, microwave, oven, stovetop
Getaway Near ORD With Great Local Amenities
Getaway Near ORD With Great Local Amenities
8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is AU$415
includes taxes & fees
11 Nov - 12 Nov
Getaway Near ORD With Great Local Amenities
Exterior detail
Vintage Urban Retreat
Vintage Urban Retreat
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is AU$849
includes taxes & fees
4 Nov - 5 Nov
Vintage Urban Retreat
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
7.8 out of 10, Good, (11)
"Very nice place "
United States
Elliot H.
The price is AU$377
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop
Updated Spacious Home -Near NWU- Hospitals+More
Updated Spacious Home -Near NWU- Hospitals+More
10.0 out of 10, Exceptional, (3)
"We had a great stay, nice neighborhood, nice home & clean home, fantastic communication with the host. Would stay here again!"
United States
Heather C.
The price is AU$701
includes taxes & fees
20 Oct - 21 Oct
Updated Spacious Home -Near NWU- Hospitals+More
Dining
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
9.6 out of 10, Exceptional, (13)
"Everything was great, most of our activities were a short drive or Uber. The beds and couch was comfortable. It was a nice stay everyone had a good time!"
United States
Israel M.
The price is AU$466
includes taxes & fees
20 Oct - 21 Oct
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Smart TV
Enamored in Elmhurst
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is AU$767
includes taxes & fees
20 Oct - 21 Oct
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
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!
9.8 out of 10, Exceptional, (19)
"Great place Great location "
United States
Josh W.
The price is AU$739
includes taxes & fees
20 Oct - 21 Oct
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Fridge, microwave, oven, stovetop
Luxury House minutes away from O'Hare and Downtown Chicago
Luxury House minutes away from O'Hare and Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is AU$858
includes taxes & fees
20 Oct - 21 Oct
Luxury House minutes away from O'Hare and Downtown Chicago
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
The price is AU$622
includes taxes & fees
26 Oct - 27 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
TV
Modern 4BR Retreat Near MDW | LCP Collection
Modern 4BR Retreat Near MDW | LCP Collection
9.4 out of 10, Exceptional, (6)
"Very nice and clean"
United States
Bobby w.
The price is AU$769
includes taxes & fees
20 Oct - 21 Oct
Modern 4BR Retreat Near MDW | LCP Collection
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!
Wonderful in Wood Dale, right by O’Hare airport!
10.0 out of 10, Exceptional, (14)
"Great property and great host!"
United States
Darin H.
The price is AU$613
includes taxes & fees
20 Oct - 21 Oct
Wonderful in Wood Dale, right by O’Hare airport!
Smart TV, video games, table football, ping pong
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
10.0 out of 10, Exceptional, (1)
"This was an excellent experience. Commu ication from Stacey (our host) was timely, accurate, and informative. The home was very clean when we arrived and the listing was accurate. The beds are very comfortable. This property is in a very quiet neighborhood. We would stay here again."
United States
Tracy G.
The price is AU$920
includes taxes & fees
27 Oct - 28 Oct
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Lovely property, well equipped and a responsive host! Would definitely recommend."
United States
Bryan S.
The price is AU$1,141
includes taxes & fees
21 Oct - 22 Oct
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug
Cozy Home by O'Hare + EV Plug
10.0 out of 10, Exceptional, (1)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
The price is AU$457
includes taxes & fees
28 Oct - 29 Oct
Cozy Home by O'Hare + EV Plug
Exterior
Chic 3bed 2bath Home with free parking close to United Center
Chic 3bed 2bath Home with free parking close to United Center
9.8 out of 10, Exceptional, (18)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is AU$1,111
includes taxes & fees
18 Nov - 19 Nov
Chic 3bed 2bath Home with free parking close to United Center
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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