North Side holiday homes

We found 2,310 holiday rentals — enter your dates for availability

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Dates

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Flexible dates

May 2025

June 2025

Holiday rentals with weekly discounts - North Side

Showing deals for:15 Aug - 22 Aug

Exceptional

(24 reviews)

Chic 2BR 2BA Condo with Balcony - River North Chicago

Chicago, Illinois

8% off

NZ$1,363 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(32 reviews)

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

NZ$871 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(226 reviews)

Spectacular Corner 2BR Penthouse in the Loop | Roof Deck

Chicago, Illinois

7% off

NZ$974 per night

includes taxes & fees

Go from traveling to relaxing in minutes with our easy check-in process

Exceptional

(127 reviews)

Kasa | Modern Studio + Steps to the South Loop | Chicago

Chicago, Illinois

8% off

NZ$527 per night

includes taxes & fees

Wake up to nice natural light though the large windows

Exceptional

(14 reviews)

Kasa | Family Friendly 3 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$1,491 per night

includes taxes & fees

Exceptional

(20 reviews)

Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago

Chicago, Illinois

8% off

NZ$1,491 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in North Side

Wrigley Field

Find the best place to stay - North Side

Beautiful Lincoln Park condominium with 4 bed, 2.5 b, luxurious gourmet kitchen.

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest

Sleeps 12 · 3 bedrooms · 2 bathrooms

The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown

Sleeps 10 · 4 bedrooms · 2 bathrooms

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)
Adagio Teas (9.7 mi / 15.6 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)
Pirates Cove Childrens Theme Park (17.9 mi / 28.8 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.