Photo by Vincent Ramundo

North Side holiday rentals

We found 2,163 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – North Side

Showing deals for:27 Nov - 4 Dec

Living area
Terrace/patio
Interior
Private kitchen
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$11,948
for 7 nights, 1 apartment
AU$1,707 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Living area
Interior
Interior
Private kitchen
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

8% off
AU$9,148
for 7 nights, 1 home
AU$1,307 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Interior
Interior
Living area
Dining
Exceptional
(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

8% off
AU$13,843
for 7 nights, 1 home
AU$1,978 per night
includes taxes & fees
Massive Queen Anne Mansion for your whole family to stay!
Kitchen
Living Room
Patio Deck 2
Bedroom 1 (King Size) + 55Inch TV
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$6,629
for 7 nights, 1 home
AU$947 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Exterior
Private kitchen
Interior
Interior
Exceptional
(27 reviews)

Stunning 6 BR Home * Chicago * Centrally Located

Chicago

7% off
AU$6,247
for 7 nights, 1 home
AU$892 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Private kitchen
Dining
Exterior
Interior
Exceptional
(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
AU$4,573
for 7 nights, 1 home
AU$653 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Living area
Private kitchen
Room
Exterior detail
Exceptional
(63 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,548
for 7 nights, 1 apartment
AU$650 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Dining room area
3 bedroom unit is top floor of historic greystone
Living room area
Living room area opens into dining room & kitchen
Exceptional
(97 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,248
for 7 nights, 1 home
AU$893 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Interior
Private kitchen
Interior
Dining
Wonderful
(49 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

8% off
AU$6,157
for 7 nights, 1 home
AU$880 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Private kitchen
Living area
Living area
Dining
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,047
for 7 nights, 1 apartment
AU$578 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Dining
Interior
Room
Interior
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$7,171
for 7 nights, 1 home
AU$1,024 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Private kitchen
Living area
Point of interest
Room
Exceptional
(14 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,797
for 7 nights, 1 home
AU$685 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Interior
Interior
Room
Living area
Wonderful
(86 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,357
for 7 nights, 1 apartment
AU$194 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Fun Mirror Wall Upstairs
Exceptional
(98 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,976
for 7 nights, 1 apartment
AU$1,854 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Private kitchen
Interior
Dining
Interior
Exceptional
(16 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$1,925
for 7 nights, 1 apartment
AU$275 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Bedroom #1 w 2 full size beds plus a desk
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Private kitchen
7 minutes drive to downtown and Millenium Park
Wonderful
(24 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,656
for 7 nights, 1 apartment
AU$379 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Room
Exterior
Dining
Interior
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,042
for 7 nights, 1 apartment
AU$1,149 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Room
Living area
Kitchen
Interior
Exceptional
(26 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
AU$2,357
for 7 nights, 1 apartment
AU$337 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Living area
Exterior detail
Dining
Room
Exceptional
(69 reviews)

Wicker Park near Downtown and the Salt Shed Labor Day Special 229.00 Sept 5-7

Chicago

7% off
AU$2,244
for 7 nights, 1 apartment
AU$321 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Labor Day Special 229.00 Sept 5-7
Private Patio
Neighborhood Photo
Private kitchen
Room
Exceptional
(36 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off
AU$2,625
for 7 nights, 1 apartment
AU$375 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Upscale kitchen with an equally spacious dining room
5 minutes drive to McCormick Place (0.9 miles)
Bedroom #1 with 2 double beds and an in-suite bathroom
Upscale kitchen with an equally spacious dining room
Wonderful
(7 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
AU$3,290
for 7 nights, 1 apartment
AU$470 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Exterior
Interior
Room
Interior
Very good
(21 reviews)

Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

Chicago

7% off
AU$2,226
for 7 nights, 1 apartment
AU$318 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Living area
Living area
Room
Exterior
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
AU$4,300
for 7 nights, 1 apartment
AU$614 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
Room
Interior
Living area
Private kitchen
Exceptional
(20 reviews)

Chicago Bear Den

Chicago

7% off
AU$2,427
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Chicago Bear Den
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your North Side getaway

Learn about the unique charm of North Side with a stay in a holiday home rental. This city has something for everyone. Wrigley Field and Lake Michigan are just a couple of the must-see attractions. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around North Side

Do you want to discover things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes North Side a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (2.4 mi / 3.9 km)
  • The Dome at the Parkway Bank Sports Complex (10.6 mi / 17.1 km)
  • Galloping Ghost (12.2 mi / 19.6 km)
  • The Glen Club (13.3 mi / 21.4 km)
  • Northbrook Sports Complex (15.7 mi / 25.2 km)
  • Harborside International Golf Center (17.1 mi / 27.5 km)

Exploring the natural features in North Side

Whether you're an active traveller or just want to appreciate the scenery, North Side is a great spot to appreciate mother nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (4.5 mi / 7.2 km)
  • Grant Park (5.1 mi / 8.2 km)
  • Lincoln Park (2.3 mi / 3.6 km)
  • Lincoln Park Conservatory (2.3 mi / 3.7 km)
  • Humboldt Park (2.3 mi / 3.7 km)
  • North Avenue Beach (3 mi / 4.7 km)

Travelling to and around North Side

If you'd prefer to travel by train, you can make your way to Chicago Clybourn Station. You can get around North Side by jumping on the metro at Paulina Station, Addison Station (Brown Line) or Southport Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in North Side?
According to our data, apartments are the most popular holiday home type in North Side. But as you might expect, everyone's idea of the perfect stay isn't going to be the same. Stayz has holiday homes of all sizes, shapes and budgets, and we'll help you locate your ideal fit.
How much does it cost to rent a holiday home in North Side?
Several things can influence what you'll pay for a holiday home in North Side, such as the type of property, season and length of stay. Still, all Stayz homes have one thing in common — excellent value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in North Side?
Prices for beach houses in North Side differ depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Stayz and how many guests to see available options and prices. From there you can use our filter tool to narrow your search by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday homes in North Side?
Pack a suitcase for the pooch in your life because North Side has 312 stays that welcome pets with open arms. Let your four-legged friend have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in North Side?
Add a whole new level of fun to your getaway by booking your crew into one of the 20 houses with a private pool in North Side. Use our search filter to find the kind of property you want on Stayz, and then spend carefree days splashing about in a swimming pool that's for your use only.
What are popular home amenities in North Side?
When it comes to home amenities that guests are on the lookout for in North Side, a swimming pool, a barbecue grill and an electric car charging station are the most popular. With Stayz holiday homes, there are options to fit your taste and style, whether you're on a trip with family members, friends or even pets.
Are there large group holiday homes in North Side?
North Side has 36 holiday homes that can cater to 10 or more guests. These properties come with the space you need to share good times with family and friends.
Are there holiday homes in North Side that welcome kids?
Bring the entire group together for an adventure in North Side at one of our 310 family-friendly properties. These stays provide conveniences that are perfect for getaways with children, including laundry facilities, multiple bedrooms and swimming pools. Simply click on the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in North Side?
You'll find loads of awesome things to do and see with the family in North Side, including:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday homes in North Side?
Take your pick from 78 one-bedroom homes in North Side. Whether you'd like a comfy cottage or an upmarket condo, Stayz's one-bedroom properties are just right if you don't require a huge amount of space. One of the best parts about having your own pad? You won't ever need to share your trip with strangers.
Can I find two-bedroom holiday homes in North Side?
North Side has 109 two-bedroom properties to pick from. Go for a holiday home with all the comfort and space you need at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in North Side?
Whether you want to keep up with the news, write a few emails or post a pic to social media, there are 83 holiday homes with WiFi in North Side. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in North Side?
Select your dates and then use the filter tool to search for holiday homes with air conditioning in North Side on Stayz. With 295 air-conditioned properties on offer here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday home in North Side?
The minimum age requirements can differ between properties on Stayz, so be sure to look at the rules of the holiday home in North Side you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in North Side for?
The length of time you can rent a holiday home in North Side differs according to the property. Just enter your selected dates to view a list of options offering extended stays. With tons of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to discover someplace just right to call your home away from home in North Side.

More holiday ideas