Search Vacation Homes in North Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for North Side vacation homes

9BR Luxurious Wrigleyville Deco House • Sleeps 20

9BR Luxurious Wrigleyville Deco House • Sleeps 20
Lakeview
10.0 out of 10, Exceptional, (1 review)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is ¥89,043
¥305,027 total
includes taxes & fees
Mar 10 - Mar 11
9BR Luxurious Wrigleyville Deco House • Sleeps 20

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"great stay"
United States
matt R.
The price is ¥11,917
¥33,306 total
includes taxes & fees
Mar 3 - Mar 4
A quiet stay while you are away

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (77 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is ¥15,318
¥30,301 total
includes taxes & fees
Feb 17 - Feb 18
Master qtr close to nature & easy urban facilities

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is ¥22,462
¥59,779 total
includes taxes & fees
Feb 11 - Feb 12
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (56 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is ¥23,423
¥51,147 total
includes taxes & fees
Feb 11 - Feb 12
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (20 reviews)
"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 ¥16,724
¥24,853 total
includes taxes & fees
Feb 11 - Feb 12
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"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 ¥22,570
¥73,569 total
includes taxes & fees
Feb 11 - Feb 12
Vintage Urban Retreat

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ¥21,861
¥43,439 total
includes taxes & fees
Feb 11 - Feb 12
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

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 bed
Maywood
8.0 out of 10, Very Good, (21 reviews)
"Very nice place "
United States
Elliot H.
The price is ¥23,188
¥46,857 total
includes taxes & fees
Feb 11 - Feb 12
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

20 min to O'Hare Airport, 20 min to Schamburg

20 min to O'Hare Airport, 20 min to Schamburg
Addison
10.0 out of 10, Exceptional, (2 reviews)
"Definitely recommend!"
United States
Jennifer H.
The price is ¥24,859
¥67,055 total
includes taxes & fees
Feb 11 - Feb 12
20 min to O'Hare Airport, 20 min to Schamburg

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ¥5,465
¥71,779 total
includes taxes & fees
Feb 16 - Feb 17
Near Lake and Museum • Modern • Game Area

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ¥15,412
¥42,150 total
includes taxes & fees
Feb 11 - Feb 12
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
8.6 out of 10, Excellent, (7 reviews)
"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 ¥28,732
¥71,509 total
includes taxes & fees
Feb 11 - Feb 12
Modern 4BR Retreat Near MDW | LCP Collection

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard
9.6 out of 10, Exceptional, (17 reviews)
"I had a great stay over the weekend with my family it was very relaxing and peaceful "
United States
Tennika W.
The price is ¥16,396
¥43,026 total
includes taxes & fees
Feb 11 - Feb 12
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
The price is ¥16,240
¥129,524 total
includes taxes & fees
Feb 11 - Feb 12
Sleeps 18 • 8BR • Game Room • Gym • Theater

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
United States
James b.
The price is ¥22,462
¥61,951 total
includes taxes & fees
Feb 12 - Feb 13
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Luxury Suite in Glen Ellyn, IL USA

Luxury Suite in Glen Ellyn, IL USA
Glen Ellyn
9.6 out of 10, Exceptional, (10 reviews)
"Was very comfortable. Had everything we needed except wash clothes. Walmart really close. "
United States
Debra B.
The price is ¥24,828
¥53,121 total
includes taxes & fees
Feb 11 - Feb 12
Luxury Suite in Glen Ellyn, IL USA

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ¥31,381
¥85,442 total
includes taxes & fees
Feb 16 - Feb 17
Oak Park Victorian by FLW Studio

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is ¥42,863
¥98,812 total
includes taxes & fees
Feb 17 - Feb 18
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Enamored in Elmhurst

Enamored in Elmhurst
Elmhurst
10.0 out of 10, Exceptional, (15 reviews)
"Clean rooms, very helpful and friendly host, the house had everything we needed"
United States
Kaitlyn M.
The price is ¥36,851
¥81,419 total
includes taxes & fees
Feb 11 - Feb 12
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.
Save an average of 15% on thousands of hotels when you're signed in

Top North Side Hotel Reviews

Find out more about North Side

North Side Vacation Homes information

Number of reviews
353
Accommodation
76 Vacation Homes
Lowest Price
¥24,853
Highest Price
¥129,524

Explore a world of travel with Expedia