Holiday Homes in Northwest Side

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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Featured Holiday Homes in Northwest Side and around

Fitness facility
Theater • Game Room • Gym • Firepit • 4BR Home

Holiday Home in Belmont Cragin

2.0 star property
Theater • Game Room • Gym • Firepit • 4BR Home
8 bedrooms, iron/ironing board, travel cot, WiFi
Sleeps 18 • 8BR • Game Room • Gym • Theater

Holiday Home in Portage Park

2.0 star property
Sleeps 18 • 8BR • Game Room • Gym • Theater
Exterior detail
Master qtr close to nature & easy urban facilities

Holiday Home in Riverwoods

9.8 out of 10, Exceptional, (73)
"Perfect secluded neighborhood. Very quiet which is what we needed to just get away from everything. Shopping and restaurants are all within 10 minutes. Owner always answered my questions right away. Would stay there again for a little retreat."
United States
Timothy
The price is €165
includes taxes & fees
7 Dec - 8 Dec
Master qtr close to nature & easy urban facilities
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Holiday Home in Worth

9.6 out of 10, Exceptional, (53)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is €294
includes taxes & fees
7 Dec - 8 Dec
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Exterior
Coziest estate home 20 minutes to downtown

Holiday Home in Willow Springs

8.8 out of 10, Excellent, (14)
"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 €354
includes taxes & fees
3 Dec - 4 Dec
Coziest estate home 20 minutes to downtown
Exterior detail
Vintage Urban Retreat

Holiday Home in Oak Park

10.0 out of 10, Exceptional, (12)
"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 €428
includes taxes & fees
9 Dec - 10 Dec
Vintage Urban Retreat
Smart TV
Getaway Near ORD With Great Local Amenities

Holiday Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is €248
includes taxes & fees
9 Dec - 10 Dec
Getaway Near ORD With Great Local Amenities
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Holiday Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is €274
includes taxes & fees
3 Dec - 4 Dec
✽ Charming Cottage ✽ close to College/Town/Station
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Maywood

7.8 out of 10, Good, (13)
"Very nice place "
United States
Elliot H.
The price is €217
includes taxes & fees
3 Dec - 4 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Holiday Home in Wood Dale

10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
Wonderful in Wood Dale, right by O’Hare airport!
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Holiday Home in La Grange Highlands

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 €266
includes taxes & fees
30 Nov - 1 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Skokie

10.0 out of 10, Exceptional, (34)
"Great!"
United States
Laura N.
The price is €583
includes taxes & fees
1 Dec - 2 Dec
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
TV
Modern 4BR Retreat Near MDW | LCP Collection

Holiday Home in Burbank

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 €414
includes taxes & fees
9 Dec - 10 Dec
Modern 4BR Retreat Near MDW | LCP Collection
Fridge, microwave, oven, stovetop
Beautiful House in Carol Stream near Downtown Chicago

Holiday Home in Carol Stream

9.6 out of 10, Exceptional, (4)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is €478
includes taxes & fees
1 Dec - 2 Dec
Beautiful House in Carol Stream near Downtown Chicago
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Holiday Home in Oak Park

10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
Modern Victorian Vibes ❤️ | Character & Charm
Smart TV
Enamored in Elmhurst

Holiday Home in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is €439
includes taxes & fees
30 Nov - 1 Dec
Enamored in Elmhurst
Dining
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Holiday Home in Lombard

9.6 out of 10, Exceptional, (15)
"I had a great stay over the weekend with my family it was very relaxing and peaceful "
United States
Tennika W.
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line

Holiday Home in Forest Park

2.0 star property
Classic Forest Park Foursquare < 1 Mi to Blue Line
Microwave, stovetop, dishwasher
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Holiday Home in Villa Park

10.0 out of 10, Exceptional, (1)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Exterior
Chic 3bed 2bath Home with free parking close to United Center

Holiday Home in Oak Park

9.8 out of 10, Exceptional, (18)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is €602
includes taxes & fees
8 Dec - 9 Dec
Chic 3bed 2bath Home with free parking close to United Center
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 Northwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"All above."
Sarina 2-night trip
Posted 1 day ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Northwest Side

Northwest Side Holiday Homes information

Number of reviews
353
Accommodation
343 Holiday Homes
Lowest Price
€165
Highest Price
€602

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