West Side Vacation Rentals, Chicago: house rentals & more

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

Top rated rentals - West Side

Clean, nice house

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Find the perfect vacation rental for your West Side getaway

Learn about the unique charm of West Side with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Grant Park and Soldier Field are just a couple of the must-sees in the area. A vacation 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

Do you want to discover things to do in the area? Venture out of your vacation home and experience everything that West Side has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

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 exciting outdoor activities or just want to appreciate the scenery, West Side is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

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 in the area. 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 vacation rental accommodation in West Side?

Based on our research, apartments are the most popular type of vacation property in West Side. But having said that, everyone's idea of an awesome trip differs. Vrbo has vacation rentals 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 vacation rental in West Side?

Season, length of stay and property type are some of the conditions that can determine the price of a vacation home. Simply add your travel dates to find your ideal fit. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals 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 Vrbo. Did someone just say "hot tub"? Use our filters to select the amenities and features you want in your beach house.

What are popular rental amenities in West Side?

The most popular rental amenities people are searching for in West Side are an oven, a fridge and a microwave oven. Whether you're vacationing with family, friends or even pets, Vrbo vacation rentals come with the best amenities for hanging out with the people closest to you.

Are there large group vacation rentals 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 vacations to special events like birthday parties and weddings, Vrbo will help you find a large group rental 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 Center
Humboldt Park

Can I find two-bedroom vacation rentals in West Side?

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

Are there vacation rentals 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 vacation homes with WiFi in West Side. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

How old do you have to be to rent a vacation rental in West Side?

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

How long can I rent a vacation rental in West Side for?

The amount of time you can book a West Side vacation 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 Vrbo vacation properties may also offer weekly or monthly discounts, so you can hang around longer for less.