Photo by Vincent Ramundo

Holiday Homes in North Side

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Our top choices for North Side holiday homes

2.0 star property
The price is AU$1,380
includes taxes & fees
28 Dec - 29 Dec
Walk to Wrigley Field! Townhouse w/ Pool Table
9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
United States
Joshua K.
The price is AU$282
includes taxes & fees
24 Dec - 25 Dec
Master qtr close to nature & easy urban facilities
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is AU$511
includes taxes & fees
4 Jan - 5 Jan 2026
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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 AU$272
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Holiday Home in Willow Springs

Coziest estate home 20 minutes to downtown
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 AU$604
includes taxes & fees
28 Dec - 29 Dec
Coziest estate home 20 minutes to downtown
8.0 out of 10, Very good, (20)
"Very nice place "
United States
Elliot H.
The price is AU$358
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Oak Park

Vintage Urban Retreat
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.
The price is AU$850
includes taxes & fees
12 Jan - 13 Jan 2026
Vintage Urban Retreat

Holiday Home in Des Plaines

Cozy Home by O'Hare + EV Plug
9.2 out of 10, Wonderful, (5)
The price is AU$431
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Home by O'Hare + EV Plug

Holiday Home in Humboldt Park

Gated Family Home w/ Chef’s Kitchen
2.0 star property
The price is AU$790
includes taxes & fees
12 Jan - 13 Jan 2026
Gated Family Home w/ Chef’s Kitchen
2.0 star property
The price is AU$747
includes taxes & fees
14 Jan - 15 Jan 2026
Game Room • Fire-pit • Playground • Gym • Billiard
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.
The price is AU$695
includes taxes & fees
11 Jan - 12 Jan 2026
Modern 4BR Retreat Near MDW | LCP Collection
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 AU$1,028
includes taxes & fees
27 Dec - 28 Dec
Chic 3bed 2bath Home with free parking close to United Center

Holiday Home in La Grange Highlands

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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 AU$439
includes taxes & fees
28 Dec - 29 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
The price is AU$1,005
includes taxes & fees
5 Jan - 6 Jan 2026
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Elmhurst

LUXE 3 BR, 2 BA + Hot Tub
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 AU$559
includes taxes & fees
1 Jan - 2 Jan 2026
LUXE 3 BR, 2 BA + Hot Tub
10.0 out of 10, Exceptional, (28)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is AU$882
includes taxes & fees
13 Jan - 14 Jan 2026
Modern Victorian Vibes ❤️ | Character & Charm
2.0 star property
The price is AU$1,410
includes taxes & fees
20 Jan - 21 Jan 2026
Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
The price is AU$620
includes taxes & fees
4 Jan - 5 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line

Holiday Home in Oakton

Your Next Vacation Home
9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
United States
Lukose K.
The price is AU$489
includes taxes & fees
12 Jan - 13 Jan 2026
Your Next Vacation Home

Holiday Home in Elmhurst

Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
Enamored in Elmhurst
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

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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