Photo by Vincent Ramundo

North Side holiday homes

We found 2,251 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – North Side

Showing deals for:15 Jan - 22 Jan

It is huge! With lots of areas for relaxing and entertaining
Our downtown Townhouse is in an amazing location
Dining
Room
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$8,994
for 7 nights, 1 home
NZ$1,285 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Interior
River North Luxury Living
Outdoors at night
French Bistro and Wine Bar - right downstairs
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
NZ$6,067
for 7 nights, 1 apartment
NZ$867 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Downstairs living room
Downstairs living area
Fun Mirror Wall Upstairs
Upstairs queen bedroom 2
Exceptional
(101 reviews)

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

Chicago

7% off
NZ$18,107
for 7 nights, 1 apartment
NZ$2,587 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Bedroom 1 (King Size) + 55Inch TV
Living Room
Front Yard View
Patio Deck 2
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
NZ$7,084
for 7 nights, 1 home
NZ$1,012 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
NZ$5,447
for 7 nights, 1 home
NZ$778 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Living area
Interior
Private kitchen
Interior
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
NZ$8,098
for 7 nights, 1 home
NZ$1,157 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Dining
Private kitchen
Living area
Exterior detail
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
NZ$5,993
for 7 nights, 1 apartment
NZ$856 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Bedroom 1 - King Bed
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(93 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
NZ$9,716
for 7 nights, 1 home
NZ$1,388 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Private kitchen
Interior
Interior
Wonderful
(50 reviews)

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

Chicago

7% off
NZ$6,233
for 7 nights, 1 home
NZ$890 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Interior
Living area
Living area
Exterior
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

8% off
NZ$8,487
for 7 nights, 1 home
NZ$1,212 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Interior
Living area
Private kitchen
Living area
Exceptional
(14 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

24% off
NZ$5,576
for 7 nights, 1 apartment
NZ$797 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Room
Dining
Terrace/patio
Living area
Exceptional
(9 reviews)

The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.

Chicago

6% off
NZ$9,264
for 7 nights, 1 apartment
NZ$1,323 per night
includes taxes & fees
The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.
Living area
Exterior detail
Property grounds
Interior
Exceptional
(7 reviews)

Private 1BR in West Rogers Park • Free Street Parking • Washer & Dryer

Chicago

7% off
NZ$3,042
for 7 nights, 1 apartment
NZ$435 per night
includes taxes & fees
Private 1BR in West Rogers Park • Free Street Parking • Washer & Dryer
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
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
Wonderful
(9 reviews)

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

Chicago

7% off
NZ$4,264
for 7 nights, 1 apartment
NZ$609 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Bedroom 3 w/ Queen Bed
Top floor kitchen and dining area
2 spots come with the unit- occupied by the van and SUV in this photo.
Kitchen on Top Floor
Exceptional
(35 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
NZ$8,630
for 7 nights, 1 apartment
NZ$1,233 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Interior
Room
Property grounds
Terrace/patio
Exceptional
(76 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
NZ$4,300
for 7 nights, 1 home
NZ$614 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Living area
Property grounds
Living area
Private kitchen
Exceptional
(113 reviews)

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chicago

15% off
NZ$3,091
for 7 nights, 1 apartment
NZ$442 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Games room
Living area
Games room
Room
Exceptional
(11 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

6% off
NZ$8,480
for 7 nights, 1 apartment
NZ$1,211 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Interior
Living area
Well stocked kitchen with Keurig coffee maker, microwave, water filter and more
Close to the beautiful Ping Tom Park and a short water taxi ride to downtown
Exceptional
(22 reviews)

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
NZ$6,513
for 7 nights, 1 apartment
NZ$930 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Exterior
Belmont Harbor
Private kitchen
Living area
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

8% off
NZ$6,606
for 7 nights, 1 home
NZ$944 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Kitchen
Living area
Interior
Dining
Exceptional
(32 reviews)

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

Chicago

7% off
NZ$2,816
for 7 nights, 1 apartment
NZ$402 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Living room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Living room area opens into dining room & kitchen
Exceptional
(101 reviews)

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

Chicago

7% off
NZ$10,534
for 7 nights, 1 home
NZ$1,505 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Interior
Rush Medical Center one of the best in the nation
Bar (on property)
Fully Equipped Kitchen
Exceptional
(375 reviews)

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Chicago

7% off
NZ$2,654
for 7 nights, 1 apartment
NZ$379 per night
includes taxes & fees
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Interior
Outdoor dining
Dining
Room
Exceptional
(50 reviews)

Lincoln Square Oasis - Bright, Clean and in Great Location

Chicago

7% off
NZ$2,521
for 7 nights, 1 apartment
NZ$360 per night
includes taxes & fees
Lincoln Square Oasis - Bright, Clean and in Great Location
  • 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)
  • Oak Brook Golf Course (14.5 mi / 23.3 km)
  • Northbrook Sports Complex (15.7 mi / 25.2 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. Bookabach 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 Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach, 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 Bookabach 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, Bookabach'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 Bookabach.
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 Bookabach 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 Bookabach. 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 Bookabach, 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