West Side Rentals by Owner
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Accessibility
- Security/Safety
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Balcony/Terrace
Why Choose Rent By Owner for your West Side vacation rental?
What makes our Rentals by Owner special?
Popular Areas for West Side Rentals by Owner
Where are the best neighborhoods to stay in West Side?
When considering where to stay in West Side, Illinois, exploring the neighborhood options can enhance your visit and ensure a comfortable, authentic experience. The West Side offers a variety of rental by owner accommodations that put you close to local charm and convenient amenities. Whether you prefer a lively area with easy access to community attractions or a quieter neighborhood for relaxation, selecting the right neighborhood in West Side can make all the difference in your trip. Trust Rent By Owner to help you find reliable vacation rentals tailored to your preferences, making your stay in this vibrant part of Illinois both seamless and enjoyable.
Downtown Chicago
Located at the heart of the city, Downtown Chicago offers easy access to the region's vibrant urban atmosphere and iconic skyline, making it a prime choice for those seeking convenience and lively surroundings.
View 1639+ Rentals in Downtown ChicagoThe Loop
This centrally situated neighborhood provides an energetic environment surrounded by cultural landmarks and transportation hubs, perfect for exploring the area's diverse attractions from a comfortable rental.
View 749+ Rentals in The LoopRiver North
Known for its dynamic arts scene and trendy dining options, this area is ideal for visitors looking to immerse themselves in the city's creative vibe while enjoying easy access to central amenities.
View 355+ Rentals in River NorthLincoln Park
With its lush parks and vibrant neighborhoods, this district offers a relaxed yet lively setting for travelers seeking a balance of outdoor activities and urban conveniences.
View 154+ Rentals in Lincoln ParkWest Loop
Famous for its burgeoning culinary scene and modern developments, the West Loop provides a trendy environment that keeps you close to the best dining and entertainment venues the region has to offer.
View 200+ Rentals in West LoopNear North Side
This bustling neighborhood combines upscale shopping, waterfront views, and vibrant nightlife, making it an excellent base for experiencing the region's sophisticated side.
View 690+ Rentals in Near North SideWicker Park
Known for its eclectic vibe and artsy culture, Wicker Park appeals to those wanting a unique stay filled with creative energy and trendy local spots within reach.
View 39+ Rentals in Wicker ParkLogan Square
This historic neighborhood offers a mix of beautiful architecture, parks, and lively local events, providing a welcoming atmosphere for travelers looking to experience authentic city life.
View 78+ Rentals in Logan SquareBest Times to Visit West Side
When should you plan your Rentals by Owner stay?
Knowing the best time to visit this destination can help you enjoy an ideal stay, whether you're seeking pleasant weather or fewer crowds while booking your rental by owner through Rent By Owner in West Side, Illinois.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours in this region, making it ideal for exploring local outdoor activities.
Fall (September to November)
This season offers pleasant temperatures and vibrant foliage, creating a picturesque setting that is perfect for sightseeing and outdoor adventures.
Off-Season Highlights
Winter (December to February)
The colder months bring lower temperatures, providing a quieter atmosphere, suitable for those seeking a peaceful retreat away from crowds.
Spring (March to May)
In early spring, the area begins to warm up with blooming flowers, offering a refreshing ambiance for visitors preferring less crowded travel periods.
Weekly Weather Forecast for West Side
How to Book Your West Side vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in West Side
Common Rentals by Owner 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
- You can enjoy a private outdoor space with a patio or deck to unwind after exploring the area.
- Look for a property that offers a barbecue grill to host memorable cookouts during your stay.
- Many rentals feature a lush yard or garden where you can relax and enjoy the fresh air.
- Some accommodations include access to a swimming pool to cool off on warm days.
- If you love outdoor activities, check for a fire pit perfect for cozy evenings with friends or family.
- Patios or verandas are common amenities, providing scenic views and comfortable seating areas.
- Outdoor dining furniture may be available, allowing you to savor meals while soaking in the local ambiance.
Top Attractions Around West Side
What attractions are nearby?
During your stay, you'll find a variety of outdoor and cultural activities nearby, allowing you to explore the vibrant attractions and scenic spots that make this destination an ideal place to enjoy your time in West Side, Illinois.
Family Activities
- Lincoln Park Zoo: Experience a day of wildlife encounters at the zoo, where you can observe animals in naturalistic habitats right within this region.
- Navy Pier: Enjoy family-friendly attractions along the waterfront, including rides, gardens, and entertainment that make for a memorable outing in the area.
- Chicago Children’s Museum: Foster your children’s creativity and learning with interactive exhibits designed to engage young minds, conveniently located nearby.
- Millennium Park: Relax and explore outdoor art installations and open green spaces here, perfect for a family picnic or a leisurely stroll in the city’s vibrant region.
Adult Activities
- Millennium Park: Explore this iconic park where you can enjoy public art installations, outdoor concerts, and stunning cityscape views right in the heart of the region.
- Navy Pier: Visit this renowned waterfront destination for scenic boat tours, lively entertainment options, and dining experiences that showcase the area's vibrant culture.
- The Art Institute of Chicago: Immerse yourself in world-class art collections and exhibitions within this historic museum nestled close to your accommodation in the region.
- Chicago Riverwalk: Take a leisurely stroll or a guided boat tour along the scenic riverfront, offering picturesque views and a range of cafes in the area.
Other Places to Stay in West Side, IL
West Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Neighborhoods: Take time to wander through the area to discover unique local spots and get a true sense of the community during your stay.
- Plan Your Transportation: Arrange reliable transportation options in advance to easily access popular destinations and maximize your time here.
- Book Early for Popular Rentals: Secure your preferred rental by owner early, especially during peak times, to ensure a comfortable and convenient stay in this destination.
- Check Out Nearby Dining Options: Enhance your visit by trying a variety of local eateries, which offer authentic flavors and a taste of regional cuisine.
Transportation Options
- Metra Train Services: You can conveniently access the area's commuter rail network for quick travel to nearby cities and attractions.
- Bus Transit Options: Local bus services offer reliable transportation within the region, making it easy to explore without a car.
- Car Rental Agencies: Several rental agencies are available nearby, giving you the flexibility to explore the destination at your own pace.
- Taxi and Rideshare Services: Taxis and ridesharing options provide on-demand transportation throughout the area, ensuring convenient arrival and departure times.
Local Customs Options
- Local Festivals and Events: Participating in community festivals and events reflects the region’s vibrant culture and offers authentic experiences during your stay.
- Respect for Local Heritage: Showing appreciation for historical landmarks and local traditions helps you connect more deeply with this destination’s unique identity.
- Dining Etiquette: Embracing regional dining customs enhances your culinary experience and demonstrates respect for local flavors and traditions.
- Community Greetings: Friendly, informal greetings are common here, fostering a welcoming atmosphere that makes your visit feel more personal and genuine.
Frequently Asked Questions About West Side Rentals by Owner
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
- 1F Chicago's Little italy Graystone nearDowntown
- Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Private Historic Coach House Wicker Park
- Spacious 4-Level/4-Bedroom Townhouse in West Loop
- Entire Below Level Studio w/Private Sauna
- Cozy Pilsen Depa
- Cozy Vintage Chicago Apartment near Downtown
2. How many Rentbyowner vacation rentals are available in West Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1111 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.
3. What is the cancellation policy for a rental by owner in West Side, Illinois?
4. How do I find out about amenities included in a rental in the West Side area?
5. Are pets allowed in rentals here, and do hosts have specific pet policies?
6. What is the check-in process for rentals by owner in this part of Illinois?
7. How do I verify the safety measures and cleanliness standards of a vacation rental in the region?
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