Far North Side holiday rentals

We found 3,121 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
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Choose a holiday rental for your Far North Side getaway

Learn about the unique charm of Far North Side with a stay in a holiday home rental. This city has something for everyone. Wrigley Field and Navy Pier are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Far North Side

Are you hoping to discover things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Far North Side a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Dome at the Parkway Bank Sports Complex (4.7 mi / 7.6 km)
  • Adagio Teas (5.7 mi / 9.2 km)
  • The Glen Club (7.8 mi / 12.5 km)
  • Lincoln Park Zoo (8.8 mi / 14.1 km)
  • Home Alone House (9.1 mi / 14.7 km)
  • Dave & Buster's (9.6 mi / 15.5 km)

Exploring the natural landscape of Far North Side

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Far North Side is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Grant Park (11.2 mi / 18.1 km)
  • Millennium Park (10.7 mi / 17.3 km)
  • Portage Park (2.1 mi / 3.4 km)
  • Norridge Park District (2.2 mi / 3.5 km)
  • Humboldt Park (6.8 mi / 10.9 km)
  • Garfield Park Conservatory (7.5 mi / 12 km)

Transport to and around Far North Side

The nearest airport is in Chicago O'Hare International Airport (ORD), located 6.3 mi (10.2 km) from the city centre.

If you prefer to travel by train, Chicago Gladstone Park Station, Chicago Norwood Park Station and Chicago Jefferson Park Station are the main stations that serve the city. You can get around Far North Side by catching a ride on the metro at Harlem-O'Hare Station, Jefferson Park Transit Center or Cumberland Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Far North Side?

Based on our research, apartments are the most in-demand holiday home type in Far North Side. But as you'd expect, everyone's idea of an epic stay isn't going to be the same. Vrbo has holiday homes with every shape, size and budget in mind, and we'll help you locate your perfect match.

How much does it cost to rent a holiday home in Far North Side?

Different things affect what you'll pay for a holiday home in Far North Side, such as the length of stay, season and type of property. However, all of our holiday homes have something in common — excellent value. Just enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Far North Side?

When you travel and the style and size of the property will help determine the cost of your beachside stay. Type in your Far North Side travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want.

What are popular home amenities in Far North Side?

A fridge, an oven and a stovetop head the list of most popular home amenities in Far North Side. Whether you're planning to travel solo, with your spouse or a group of family members, Vrbo will help you find a holiday home that fits your style with a load of extras you'll love.

Are there large group holiday homes in Far North Side?

You can pick from eight properties in Far North Side that can accommodate a group of 10 or more people. Whether you're organising a get-together with extended family or some kind of special event, there's enough room to get your loved ones together under the same roof.

What are the top attractions for families in Far North Side?

Keep the kids occupied at these fun family-friendly attractions in Far North Side:

  • Kathy Osterman Beach
  • Foster Avenue Beach
  • Loyola Beach

Can I find two-bedroom holiday homes in Far North Side?

Take your pick of 27 two-bedroom homes in Far North Side. Put your little ones in the second room or maybe fill it with a couple of your nearest and dearest friends. There's a spot for whoever's lucky enough to be coming along for the ride.

Are there holiday homes with WiFi in Far North Side?

Far North Side has 59 holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it a breeze to go online.

How old do you have to be to rent a holiday home in Far North Side?

We advise checking with the Far North Side holiday home you want on Vrbo as age restrictions differ. However, it's typically 16, 18 or 21.

How long can I rent a holiday home in Far North Side for?

How long you can rent a holiday home in Far North Side depends on the property. Simply enter your preferred travel dates to display a list of options offering extended stays. With many features like air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to find somewhere just right to call your home away from home in Far North Side.