Photo by Vincent Ramundo
Holiday Homes in North Side
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Our top choices for North Side holiday homes
Holiday Home in Lakeview
Walk to Wrigley Field! Townhouse w/ Pool TableThe price is AU$1,380
includes taxes & fees
28 Dec - 29 Dec
Holiday Home in Riverwoods
Master qtr close to nature & easy urban facilities9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
Joshua K.
The price is AU$282
includes taxes & fees
24 Dec - 25 Dec
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 AU$511
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.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 AU$272
includes taxes & fees
5 Jan - 6 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 AU$604
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 AU$358
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 AU$850
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Des Plaines
Cozy Home by O'Hare + EV Plug9.2 out of 10, Wonderful, (5)
The price is AU$431
includes taxes & fees
5 Jan - 6 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.
Top North Side Hotel Reviews
Best Western Plus Hawthorne Terrace Hotel
10/10 Excellent
Find out more about North Side
North Side Holiday Homes information
Number of reviews | 382 |
|---|---|
Accommodation | 76 Holiday Homes |
Lowest Price | AU$272 |
Highest Price | AU$1,410 |
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