Holiday rentals with weekly discounts – Northwest Side
Showing deals for:12 Feb - 19 Feb
Image gallery for Chicago Gold Coast Mansion 6 Bed Luxury Retreat
1010 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Chicago Gold Coast Mansion 6 Bed Luxury Retreat
Chicago
7% off
Price is AU$27,638
AU$27,638
for 7 nights, 1 home
AU$3,948 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10, Exceptional, (107 reviews)
Exceptional
(107 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago
7% off
Price is AU$4,691
AU$4,691
for 7 nights, 1 apartment
AU$670 per night
includes taxes & fees
Image gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Exceptional Location!
9.89.8 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Exceptional Location!
Chicago
8% off
Price is AU$14,239
AU$14,239
for 7 nights, 1 apartment
AU$2,034 per night
includes taxes & fees
Image gallery for Stunning Lincoln Park Single-Family House with Fantastic Game Room
1010 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
11% off
Price is AU$10,103
AU$10,103
for 7 nights, 1 home
AU$1,443 per night
includes taxes & fees
Image gallery for NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Chicago
8% off
Price is AU$6,625
AU$6,625
for 7 nights, 1 home
AU$946 per night
includes taxes & fees
Image gallery for Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Chicago
15% off
Price is AU$4,239
AU$4,239
for 7 nights, 1 home
AU$606 per night
includes taxes & fees
Image gallery for Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
Chicago
11% off
Price is AU$6,356
AU$6,356
for 7 nights, 1 home
AU$908 per night
includes taxes & fees
Image gallery for Wonderful in Wood Dale, right by O’Hare airport!
9.69.6 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
13% off
Price is AU$4,116
AU$4,116
for 7 nights, 1 home
AU$588 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.89.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago
8% off
Price is AU$5,969
AU$5,969
for 7 nights, 1 home
AU$853 per night
includes taxes & fees
Image gallery for The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Chicago
7% off
Price is AU$7,722
AU$7,722
for 7 nights, 1 apartment
AU$1,103 per night
includes taxes & fees
Image gallery for Gorgeous 7BD Home w/ Garage
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Gorgeous 7BD Home w/ Garage
Chicago
8% off
Price is AU$8,157
AU$8,157
for 7 nights, 1 home
AU$1,165 per night
includes taxes & fees
Image gallery for Beautiful Berwyn Bungalow Close to Downtown Chicago
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Beautiful Berwyn Bungalow Close to Downtown Chicago
Berwyn
8% off
Price is AU$3,377
AU$3,377
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
Image gallery for Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
8% off
Price is AU$1,652
AU$1,652
for 7 nights, 1 apartment
AU$236 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house with cinema room massage chair in peaceful Evanston
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Charming 3-bedroom house with cinema room massage chair in peaceful Evanston
Evanston
8% off
Price is AU$3,791
AU$3,791
for 7 nights, 1 home
AU$542 per night
includes taxes & fees
Image gallery for Premier 4BR Art Deco suite with garage.
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Premier 4BR Art Deco suite with garage.
Chicago
6% off
Price is AU$6,909
AU$6,909
for 7 nights, 1 apartment
AU$987 per night
includes taxes & fees
Image gallery for Steps from the “L” train to Wrigley & Downtown
1010 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago
8% off
Price is AU$4,873
AU$4,873
for 7 nights, 1 apartment
AU$696 per night
includes taxes & fees
Image gallery for The En Bronze ~ 7mins To Dining & Downtown Chicago
9.29.2 out of 10, Wonderful, (9 reviews)
Wonderful
(9 reviews)
The En Bronze ~ 7mins To Dining & Downtown Chicago
Chicago
7% off
Price is AU$5,855
AU$5,855
for 7 nights, 1 apartment
AU$836 per night
includes taxes & fees
Image gallery for The Exclusive- 7 Bed, 6 Bath Retreat
9.89.8 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
The Exclusive- 7 Bed, 6 Bath Retreat
Chicago
5% off
Price is AU$7,195
AU$7,195
for 7 nights, 1 apartment
AU$1,028 per night
includes taxes & fees
Image gallery for Wrigley Field/Lakeview -Entire Home- Large Groups!
9.89.8 out of 10, Exceptional, (116 reviews)
Exceptional
(116 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
11% off
Price is AU$7,685
AU$7,685
for 7 nights, 1 home
AU$1,098 per night
includes taxes & fees
Image gallery for A home away from home! <No events allowed>
9.69.6 out of 10, Exceptional, (160 reviews)
Exceptional
(160 reviews)
A home away from home! <No events allowed>
Chicago
7% off
Price is AU$2,552
AU$2,552
for 7 nights, 1 home
AU$365 per night
includes taxes & fees
Image gallery for Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-EV Charger
9.49.4 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-EV Charger
Chicago
22% off
Price is AU$2,824
AU$2,824
for 7 nights, 1 home
AU$403 per night
includes taxes & fees
Image gallery for 2,400 SF 4BR + 2 Parking | Steps to Wrigley
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
2,400 SF 4BR + 2 Parking | Steps to Wrigley
Chicago
8% off
Price is AU$6,507
AU$6,507
for 7 nights, 1 apartment
AU$930 per night
includes taxes & fees
Image gallery for Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
1010 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
7% off
Price is AU$8,187
AU$8,187
for 7 nights, 1 home
AU$1,170 per night
includes taxes & fees
Image gallery for Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
9.89.8 out of 10, Exceptional, (123 reviews)
Exceptional
(123 reviews)
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Chicago
23% off
Price is AU$2,204
AU$2,204
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Northwest Side
Exotic House - Few minutess from O'Hare and Chicago
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Lonestar 3 Bedroom House nearby Hospital district /TJC, TV’s in all BDRMS.
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Gated 2BR w Garage | Close to Hospitals & Colleges
Sleeps 8 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
King Bed • 2BR • Sleeps 13 • Historic Location
Sleeps 13 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently Asked Questions
How much does it cost to rent a holiday home in Northwest Side?
The average price for a holiday home in Northwest Side depends on several factors, including season, property type and length of stay. Whether you're searching for a sprawling villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your travel dates to discover stays with unbeatable value.
How much does it cost to rent a beach house in Northwest Side?
When you travel and the style and size of the property will influence the cost of your beachside escape. Enter your Northwest Side travel dates to view your available options on Stayz. Did someone just say "private pool"? Use the filters to pick the amenities and features you want in your holiday home.
How old do you have to be to rent a holiday home in Northwest Side?
The minimum required age is normally 16, 18 or 21. It can change from one property to another on Stayz, so check the rules of your chosen Northwest Side holiday home before booking your escape.
How long can I rent a holiday home in Northwest Side for?
The amount of time you can stay in a Northwest Side holiday home for depends on each property. Simply put in your preferred travel dates to browse options that offer long-term stays. They feature everything you need to make your extended trip more convenient and comfortable, like air conditioning and kitchens. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.