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Northwest Side holiday homes

We found 3,166 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Northwest Side

Showing deals for:26 Dec - 2 Jan
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  • 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

Find the perfect holiday rental for your Northwest Side getaway

Learn about the unique charm of Northwest Side with a stay in a holiday home rental. This city has something for everyone. Wrigley Field and Michigan Avenue are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Northwest Side

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Northwest Side has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (7 mi / 11.2 km)
  • Dave & Buster's (7.5 mi / 12 km)
  • Galloping Ghost (9.8 mi / 15.8 km)
  • The Glen Club (10.7 mi / 17.2 km)
  • Pirates Cove Childrens Theme Park (13.4 mi / 21.5 km)
  • LEGOLAND® Discovery Center (15.3 mi / 24.7 km)

Exploring the natural features in Northwest Side

Whether you're looking for adventure or just want to appreciate the scenery, Northwest Side is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (8.4 mi / 13.6 km)
  • Grant Park (8.9 mi / 14.3 km)
  • Portage Park (0.9 mi / 1.4 km)
  • Humboldt Park (4.2 mi / 6.7 km)
  • Garfield Park Conservatory (4.6 mi / 7.5 km)
  • Garfield Park (4.8 mi / 7.7 km)

Transport to and around Northwest Side

If you prefer to travel by train, Chicago Grayland Station, Chicago Mayfair Station and Chicago Hanson Park Station are the main stations in the city. You can see more of Northwest Side by catching a ride on the metro at Montrose Station (Blue Line), Irving Park Station (Blue Line) or Addison Station (Blue Line).

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 Bookabach. 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 Bookabach, 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 Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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