Photo by Phil Ostroff
Holiday Homes in Central Chicago
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Our top choices for Central Chicago holiday homes
Holiday Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.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."
Karen D.
The price is NZ$307
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Worth
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is NZ$576
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Willow Springs
Coziest estate home 20 minutes to downtown8.8 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!"
Gabriela N.
The price is NZ$681
includes taxes & fees
28 Dec - 29 Dec
Holiday Home in Maywood
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed8.0 out of 10, Very good, (20)
"Very nice place "
Elliot H.
The price is NZ$404
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in Oak Park
Vintage Urban Retreat10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
Thomas P.
The price is NZ$917
includes taxes & fees
14 Jan - 15 Jan 2026
Holiday Home in Des Plaines
Cozy Home by O'Hare + EV Plug9.2 out of 10, Wonderful, (5)
The price is NZ$582
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Humboldt Park
Gated Family Home w/ Chef’s KitchenThe price is NZ$874
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Home in Belmont Cragin
Game Room • Fire-pit • Playground • Gym • BilliardThe price is NZ$842
includes taxes & fees
14 Jan - 15 Jan 2026
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
InterContinental Chicago Magnificent Mile by IHG
10/10 Excellent
Find out more about Central Chicago
Central Chicago Holiday Homes information
Number of reviews | 309 |
|---|---|
Accommodation | 27 Holiday Homes |
Lowest Price | NZ$307 |
Highest Price | NZ$1,590 |
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