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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 Table
Holiday Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.9.8 out of 10, Exceptional, (17)
"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$309
includes taxes & fees
5 Jan - 6 Jan 2026
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 NZ$334
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, (55)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is NZ$581
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$682
includes taxes & fees
9 Jan - 10 Jan 2026
Holiday Home in La Grange Highlands
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
Arnie B.
Holiday Home in Westchester
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 "
Josh W.
The price is NZ$709
includes taxes & fees
5 Jan - 6 Jan 2026
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$406
includes taxes & fees
4 Jan - 5 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
City Suites Hotel
10/10 Excellent
Find out more about North Side
North Side Holiday Homes information
Number of reviews | 364 |
|---|---|
Accommodation | 76 Holiday Homes |
Lowest Price | NZ$309 |
Highest Price | NZ$1,140 |
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