Photo by Phil Ostroff

Holiday Homes in Central Chicago

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Central Chicago holiday homes

Property grounds
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
2.0 star property
Robertsdale
9.8 out of 10, Exceptional, (16)
"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 €156
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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 €292
includes taxes & fees
4 Jan - 5 Jan 2026
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop
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 €346
includes taxes & fees
28 Dec - 29 Dec
Coziest estate home 20 minutes to downtown
Smart TV
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, (20)
"Very nice place "
United States
Elliot H.
The price is €204
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Interior
Vintage Urban Retreat

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
Vintage Urban Retreat
Interior
Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.2 out of 10, Wonderful, (5)
The price is €295
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Home by O'Hare + EV Plug
Fridge, microwave, oven, stovetop
Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen
2.0 star property
Humboldt Park
Gated Family Home w/ Chef’s Kitchen
Fridge, microwave, oven, stovetop
Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
2.0 star property
Belmont Cragin
Game Room • Fire-pit • Playground • Gym • Billiard
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.
Modern 4BR Retreat Near MDW | LCP Collection
Interior
Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (18)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
The price is €588
includes taxes & fees
27 Dec - 28 Dec
Chic 3bed 2bath Home with free parking close to United Center
2 bedrooms, iron/ironing board, WiFi, bed sheets
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 €258
includes taxes & fees
30 Dec - 31 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Dining
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 €320
includes taxes & fees
1 Jan - 2 Jan 2026
LUXE 3 BR, 2 BA + Hot Tub
Exterior detail
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm
Oak Park
10.0 out of 10, Exceptional, (28)
"Great location and walkable to restaurants. "
United States
Laura B.
Modern Victorian Vibes ❤️ | Character & Charm
Private kitchen
Your Next Vacation Home

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
United States
Lukose K.
The price is €315
includes taxes & fees
24 Jan - 25 Jan 2026
Your Next Vacation Home
Dining
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 €1,246
includes taxes & fees
24 Jan - 25 Jan 2026
Sleeps 18 • 8BR • Game Room • Gym • Theater
Smart TV, fireplace, books, video library
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)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is €732
includes taxes & fees
24 Jan - 25 Jan 2026
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
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.
Enamored in Elmhurst
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 €354
includes taxes & fees
24 Jan - 25 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Fridge, microwave, oven, stovetop
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
Cozy Home in Suburbs near Chicago - pet friendly
Smart TV
Spacious 4-bedroom house, Free parking, close to O'hare

Spacious 4-bedroom house, Free parking, close to O'hare

Spacious 4-bedroom house, Free parking, close to O'hare
Glenview
Spacious 4-bedroom house, Free parking, close to O'hare
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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!"
Carol 3-night trip
Posted 23 hours ago
Palmer House a Hilton Hotel

Find out more about Central Chicago

Central Chicago Holiday Homes information

Number of reviews
309
Accommodation
23 Holiday Homes
Lowest Price
€156
Highest Price
€1,246

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