West Side, Chicago holiday accommodation: short-term house rentals & properties

Find spaces that suit your style

Find properties near top attractions in West Side

Wrigley Field

Find the best place to stay - West Side

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

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

Sleeps 20 · 5 bedrooms · 2+ bathrooms

Top rated rentals - West Side

Premier Host

Lovely stay in a nice neighbourhood which felt like a home as had everything you need.

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

Find the perfect holiday rental for your West Side getaway

Learn about the unique charm of West Side with a stay in a holiday home rental. This city has something for everyone. Grant Park and Soldier Field are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around West Side

Are you looking for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes West Side a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Dave & Buster's (4.3 mi / 6.9 km)
Lincoln Park Zoo (4.9 mi / 7.9 km)
Galloping Ghost (8.6 mi / 13.9 km)
The Dome at the Parkway Bank Sports Complex (11.2 mi / 18 km)
Oak Brook Golf Course (11.6 mi / 18.7 km)
Adagio Teas (13 mi / 20.9 km)

Exploring the natural landscape of West Side

Whether you're looking for fun outdoor activities or just want to take in the scenery, West Side is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Grant Park (4.5 mi / 7.3 km)
Millennium Park (4.4 mi / 7.1 km)
Garfield Park (0.6 mi / 1 km)
Garfield Park Conservatory (0.8 mi / 1.3 km)
Anna and Frederick Douglass Park (1.1 mi / 1.7 km)
Humboldt Park (2 mi / 3.2 km)

How to get to and around West Side

If you prefer to travel by train, Chicago Kedzie Station, Chicago Western Avenue Station (Milwaukee District-West) and Chicago Western Avenue Station (BNSF) are the main stations that serve the city. You can get around West Side by jumping on the metro at Kedzie-Homan Station, Kedzie Station (Green Line) or Conservatory-Central Park Drive Station.

Frequently asked questions

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

Based on our research, apartments are the most popular type of holiday property in West Side. But having said that, everyone's idea of an awesome trip differs. Stayz has holiday homes of all sizes and shapes, and we'll help you discover the best fit for your needs.

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

Season, length of stay and property type are some of the conditions that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From comfy cabins to expansive luxury villas, all Stayz holiday homes provide unbeatable value.

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

When you travel and the style and size of the property will help determine the cost of your beachside escape. Put in your West Side travel dates to see your options on Stayz. Did someone just say "hot tub"? Use our filters to select the amenities and features you want in your beach house.

What are popular home amenities in West Side?

The most popular home amenities people are searching for in West Side are an oven, a fridge and a microwave oven. Whether you're holidaying with family, friends or even pets, Stayz holiday homes come with the best amenities for hanging out with the people closest to you.

Are there large group holiday homes in West Side?

With 26 properties that can sleep 10 or more people in West Side, you won't have to limit the invite list. From fun family holidays to special events like birthday parties and weddings, Stayz will help you find a large group home to suit the occasion.

What are the top attractions for families in West Side?

Keep the kids happy at these top family-friendly attractions in West Side:

Anna and Frederick Douglass Park
United Centre
Humboldt Park

Can I find two-bedroom holiday homes in West Side?

Take off with your loved ones and experience complete comfort and privacy in one of the 84 two-bedroom holiday homes West Side has to offer.

Are there holiday homes with WiFi in West Side?

Whether you want to keep up with the latest headlines, look over emails or update your social media, there are 103 holiday homes with WiFi in West Side. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

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

You'll need to check with the West Side holiday property you'd like on Stayz as age restrictions vary. However, it's typically 16, 18 or 21.

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

The amount of time you can book a West Side holiday home for varies depending on the property. Simply put in your dates of travel to find available options offering extended stays. They have all the things you need to make your extended trip more comfortable and enjoyable, like kitchens and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can hang around longer for less.