Best Vacation Homes in West Side
10.0
Oceanfront
Parking
Ocean View
View
10.0- Parking
Balcony/Terrace
Air Conditioner
Internet
9.8
Breakfast
Kitchen- Air Conditioner
- Internet
10.0- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
10.0- Parking
- View
- Air Conditioner
- Internet
10.0- Kitchen
- Air Conditioner
- Internet
Wheelchair Accessible
10.0
Hot Tub- Parking
Pool- Balcony/Terrace
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
West Side Luxury Rentals
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
9.4- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
10.0- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
Child Friendly
West Side Pet Friendly Vacation Rentals
10.0- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
10.0- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
- Parking
- Kitchen
- Air Conditioner
- Internet
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Air Conditioner
- Internet
Pet Friendly
Sports/Activities
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
West Side Large Vacation Homes
10.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Parking
- Air Conditioner
- Internet
- Child Friendly
9.0- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
10.0- Parking
- Air Conditioner
- Internet
- Child Friendly
2.0- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
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- Air Conditioner
Why Choose Rent By Owner for your West Side Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for West Side Vacation Rentals
Where are the best neighborhoods to stay in West Side?
When exploring the West Side of Illinois, you’ll find a variety of neighborhoods that offer unique charm and easy access to local attractions. Each area provides a different atmosphere, making it simple to find the perfect place to stay during your visit. Whether you're seeking a lively neighborhood with vibrant culture or a quieter spot for relaxation, the West Side’s diverse communities cater to all preferences. Booking your ideal vacation rental in this region ensures an authentic experience, complemented by the convenience and reliability you expect from a trusted platform.
Downtown Chicago
In this vibrant part of the city, you’ll find a lively urban atmosphere with easy access to the region’s best dining, shopping, and entertainment options. Staying here places you right in the heart of the action, making it ideal for exploring the city's dynamic culture.
View 1184+ Rentals in Downtown ChicagoThe Loop
This central area is perfect for those who want to experience the city's iconic skyline and bustling business district. Your stay here offers convenient proximity to major attractions and a lively downtown vibe that captures the essence of the region.
View 548+ Rentals in The LoopRiver North
Known for its vibrant arts scene and trendy nightlife, this neighborhood is an excellent choice for travelers seeking stylish accommodations close to cultural hotspots. Staying here allows you to immerse yourself in the region’s creative energy and sophisticated eateries.
View 278+ Rentals in River NorthLincoln Park
Offering a more relaxed atmosphere, this neighborhood combines beautiful park views with charming boutiques and cafes. It’s an ideal spot to enjoy the region's natural beauty while remaining within reach of the city’s main attractions.
View 116+ Rentals in Lincoln ParkWest Loop
Renowned for its innovative culinary scene and modern loft-style accommodations, this area appeals to travelers looking for trendy, upscale lodging options. Staying here provides a convenient base to explore the region’s thriving food culture.
View 156+ Rentals in West LoopNear North Side
This upscale neighborhood offers a blend of luxury and accessibility, with high-end dining, shopping, and waterfront views. It’s a prime choice for visitors wanting to experience the region’s sophisticated side.
View 480+ Rentals in Near North SideWicker Park
Famous for its hipster vibe and eclectic storefronts, this neighborhood draws those wanting to enjoy arts, music, and unique local cafes. Staying here puts you in the midst of a creative community within the regional hub.
View 38+ Rentals in Wicker ParkLogan Square
Known for its lively street festivals and diverse culinary options, this area offers a more laid-back yet culturally rich experience. It’s an excellent destination for travelers seeking an authentic taste of the local scene.
View 47+ Rentals in Logan SquareBest Times to Visit West Side
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you can enjoy its local charm and outdoor activities at their best, making your stay in the region truly memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences its peak season as visitors flock here to enjoy warm weather and outdoor activities. Booking your vacation rentals early ensures you secure the best options in the region.
Fall (September to November)
Autumn draws many travelers looking to experience the vibrant foliage and pleasant climate. Securing your accommodations during this time provides a comfortable stay amid scenic surroundings in the area.
Off-Season Highlights
Winter (December to February)
The cold winter months see fewer visitors, making it an ideal period for those seeking quieter getaways. You can often find better deals on vacation rentals during this off-peak time.
Spring (March to May)
Early spring offers mild weather and fewer crowds, providing a peaceful setting for your stay. Planning ahead allows you to find cozy vacation rentals at more affordable rates.
Weekly Weather Forecast for West Side
How to Book Your West Side Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in West Side
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck perfect for relaxing after a day of exploring the area.
- Take advantage of a well-maintained garden or yard, ideal for outdoor activities or family gatherings.
- Relax by an outdoor swimming pool, offering a refreshing escape during warm weather.
- Utilize outdoor grilling facilities to prepare delicious meals alfresco with friends and family.
- Make use of dedicated outdoor dining spaces that provide a scenic setting for your meals.
- Benefit from access to nearby parks or green spaces for picnics, walking, or cycling adventures.
- Experience the convenience of off-street parking amenities suited for vehicles of all sizes.
Top Attractions Around West Side
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities, cultural experiences, and local attractions that offer a perfect blend of leisure and adventure during your stay.
Family Activities
- Lincoln Park Zoo: Spend a day exploring this free zoo, where you can enjoy close-up encounters with animals and engaging educational exhibits suitable for all ages.
- Shedd Aquarium: Discover a fascinating underwater world at this renowned aquarium, offering interactive displays and family-friendly marine life shows in the region.
- Maggie Daley Park: Enjoy outdoor adventures at this scenic park with climbing walls, playgrounds, and beautiful views of the city skyline designed for family fun.
- The Field Museum: Dive into natural history at this famous museum, where your family can explore engaging exhibits on dinosaurs, ancient civilizations, and more right here in the area.
Adult Activities
- Explore the Chicago Riverwalk: You can enjoy a scenic stroll along the river, taking in stunning city views and vibrant local life right in this part of Illinois.
- Visit the Art Institute of Chicago's nearby exhibits: This renowned cultural institution offers impressive collections that are easily accessible and showcase the region’s rich artistic heritage.
- Relax at Millennium Park: An iconic urban park where you can unwind, admire unique public art installations, and experience the lively atmosphere just a short distance away.
- Discover Navy Pier: A popular destination offering entertainment, dining, and scenic boat cruises, perfect for immersing yourself in the area's vibrant scene.
Other Places to Stay in West Side, IL
West Town
Near West Side
West Loop
East Village
University Village / Little Italy
River West
Wicker Park
Lower West Side
Pulaski Park
Noble Square
West Loop Gate
Heart of Chicago
West Side Travel Tips
How Can You Make the Most of Your Stay?
- Research local attractions and dining options: Take some time to explore what the area offers so you can plan activities that make your stay memorable without missing out on hidden gems.
- Choose a well-located vacation rental: Opt for properties close to key sites and transportation, ensuring easy access to everything this destination has to offer.
- Plan your itinerary in advance: Organize your days around the region’s highlights to maximize your time and enjoy a diverse range of experiences during your visit.
- Communicate with your host or property manager: Clarify any questions prior to arrival to ensure a smooth check-in and a comfortable stay at your chosen vacation rental here.
Transportation Options
- Chicago Transit Authority (CTA): The CTA offers extensive bus and train services that make exploring the area convenient for visitors staying in this part of Illinois.
- Metra Commuter Rail: Providing reliable rail connections to downtown Chicago and beyond, Metra is an efficient option for those looking to venture outside the region with ease.
- Taxi and Rideshare Services: Local taxi companies and rideshare options like Uber and Lyft are readily available here, offering flexible transportation throughout the region.
- Rental Car Services: Several rental agencies operate nearby, giving you the freedom to explore the area at your own pace from your vacation rental here.
Local Customs Options
- Local Cuisine Appreciation: Engaging with the region’s culinary customs means sampling traditional dishes that reflect its rich cultural heritage, offering a genuine taste of your destination.
- Respect for Community Events: Participating in or observing local festivals and parades provides an authentic connection to the area's vibrant traditions and social fabric.
- Greeting Etiquette: Understanding customary greetings here ensures respectful interactions with residents and enhances your cultural experience during your stay.
- Environmental Respect: Practicing eco-friendly habits aligns with the community's values, helping you enjoy your visit while preserving the area's natural beauty.
Frequently Asked Questions About West Side?
1. What are the top vacation rentals in West Side?
There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in West Side:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Spacious 4-Level/4-Bedroom Townhouse in West Loop
- Spacious 3/2 Duplex In Wicker Park Area
- Ukrainian Village 3BR/3BA Private Patio, Parking
2. How many vacation rentals have private pools in West Side?
There are 6 vacation rentals with private pools near West Side. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in West Side are best for families?
If you are looking for a family-friendly vacation home in West Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in West Side:
4. How many Rentbyowner vacation rentals are available in West Side?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1581 in the West Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in West Side.
5. What is the cancellation policy for vacation rentals in this area?
6. Are there any specific requirements or restrictions when booking a vacation rental here?
7. How do I ensure my booking is secure and reliable?
8. What amenities are typically included in the vacation rentals in this region?
9. Is there a flexible check-in and check-out process available?
West Side Top Rated Vacation Rentals
10.0- Hot Tub
- Parking
- Pool
- Balcony/Terrace
10.0- Hot Tub
- Parking
- Pool
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10.0- Hot Tub
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- Pool
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10.0- Parking
- Pool
- Balcony/Terrace
- Kitchen
10.0- Hot Tub
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- Pool
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10.0- Hot Tub
- Parking
- Pool
- Balcony/Terrace
10.0- Parking
- Pool
- Balcony/Terrace
- Kitchen
10.0- Parking
- Pool
- Kitchen
- Air Conditioner
