Photo by Vincent Ramundo
Holiday Homes in North Side
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Our top choices for North Side holiday homes
Walk to Wrigley Field! Townhouse w/ Pool Table
Walk to Wrigley Field! Townhouse w/ Pool TableLakeview
The price is €789
includes taxes & fees
28 Dec - 29 Dec
Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilitiesRiverwoods
9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
Joshua K.
The price is €179
includes taxes & fees
20 Jan - 21 Jan 2026
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-FiWorth
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is €293
includes taxes & fees
4 Jan - 5 Jan 2026
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.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."
Karen D.
The price is €157
includes taxes & fees
5 Jan - 6 Jan 2026
Coziest estate home 20 minutes to downtown
Coziest estate home 20 minutes to downtownWillow 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!"
Gabriela N.
The price is €346
includes taxes & fees
28 Dec - 29 Dec
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 bedMaywood
8.0 out of 10, Very good, (20)
"Very nice place "
Elliot H.
The price is €205
includes taxes & fees
29 Dec - 30 Dec
Vintage Urban Retreat
Vintage Urban RetreatOak 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."
Thomas P.
The price is €487
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy Home by O'Hare + EV Plug
Cozy Home by O'Hare + EV PlugDes Plaines
9.2 out of 10, Wonderful, (5)
The price is €247
includes taxes & fees
3 Jan - 4 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 North Side Hotel Reviews
Hotel Lincoln
10/10 Excellent
Find out more about North Side
North Side Holiday Homes information
Number of reviews | 382 |
|---|---|
Accommodation | 76 Holiday Homes |
Lowest Price | €157 |
Highest Price | €789 |
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