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Holiday Homes in Central Chicago

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Central Chicago holiday homes

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.

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
2.0 star property
Robertsdale
9.8 out of 10, Exceptional, (15)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
The price is AU$306
includes taxes & fees
14 Dec - 15 Dec
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*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, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is AU$501
includes taxes & fees
14 Dec - 15 Dec
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Exterior
Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown
Willow Springs
8.8 out of 10, Excellent, (16)
"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$603
includes taxes & fees
14 Dec - 15 Dec
Coziest estate home 20 minutes to downtown
Smart TV
Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities
Des Plaines
9.0 out of 10, Wonderful, (4)
"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$422
includes taxes & fees
15 Dec - 16 Dec
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop
Modern Apt in Trendy Neighborhood w/ Free Parking

Modern Apt in Trendy Neighborhood w/ Free Parking

Modern Apt in Trendy Neighborhood w/ Free Parking
2.0 star property
Avondale
The price is AU$280
includes taxes & fees
16 Dec - 17 Dec
Modern Apt in Trendy Neighborhood w/ Free Parking
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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (19)
"Very nice place "
United States
Elliot H.
The price is AU$353
includes taxes & fees
14 Dec - 15 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Terrace/patio
Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
2.0 star property
Belmont Cragin
The price is AU$825
includes taxes & fees
5 Jan - 6 Jan 2026
Theater • Game Room • Gym • Firepit • 4BR Home
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

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, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is AU$428
includes taxes & fees
16 Dec - 17 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (13)
"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 AU$815
includes taxes & fees
17 Dec - 18 Dec
Vintage Urban Retreat
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
The price is AU$596
includes taxes & fees
15 Dec - 16 Dec
Wonderful in Wood Dale, right by O’Hare airport!
Smart TV
Enamored in Elmhurst

Enamored in Elmhurst

Enamored in Elmhurst
2.0 star property
Elmhurst
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is AU$747
includes taxes & fees
15 Dec - 16 Dec
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
The price is AU$1,063
includes taxes & fees
5 Jan - 6 Jan 2026
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
The price is AU$500
includes taxes & fees
17 Dec - 18 Dec
LUXE 3 BR, 2 BA + Hot Tub
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm
Oak Park
10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is AU$829
includes taxes & fees
15 Dec - 16 Dec
Modern Victorian Vibes ❤️ | Character & Charm
TV
Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
9.4 out of 10, Exceptional, (6)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is AU$694
includes taxes & fees
8 Jan - 9 Jan 2026
Modern 4BR Retreat Near MDW | LCP Collection
Microwave, oven, stovetop, dishwasher
Cozy Home in Suburbs near Chicago - pet friendly

Cozy Home in Suburbs near Chicago - pet friendly

Cozy Home in Suburbs near Chicago - pet friendly
2.0 star property
Bridgeview
The price is AU$491
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Home in Suburbs near Chicago - pet friendly
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
Forest Park
The price is AU$619
includes taxes & fees
17 Dec - 18 Dec
Classic Forest Park Foursquare < 1 Mi to Blue Line
Private kitchen
Great Location! Beautiful Home Near Downtown Westmont

Great Location! Beautiful Home Near Downtown Westmont

Great Location! Beautiful Home Near Downtown Westmont
Westmont
9.8 out of 10, Exceptional, (11)
"Great property. Great host. Would stay again."
United States
Aliasger S.
The price is AU$279
includes taxes & fees
19 Dec - 20 Dec
Great Location! Beautiful Home Near Downtown Westmont
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.0 out of 10, Wonderful, (4)
"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$430
includes taxes & fees
21 Dec - 22 Dec
Cozy Home by O'Hare + EV Plug
8 bedrooms, iron/ironing board, travel cot, WiFi
Sleeps 18 • 8BR • Game Room • Gym • Theater

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
Portage Park
The price is AU$1,384
includes taxes & fees
7 Jan - 8 Jan 2026
Sleeps 18 • 8BR • Game Room • Gym • Theater
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 Central Chicago Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great place always. "
Robert 1-night trip
Posted 3 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Central Chicago

Central Chicago Holiday Homes information

Number of reviews
265
Accommodation
27 Holiday Homes
Lowest Price
AU$279
Highest Price
AU$1,384

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