Near West Side Rentals by Owner
- Air Conditioner
- Accessibility
- Security/Safety
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
Why Choose Rent By Owner for your Near West Side vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Near West Side Rentals by Owner
Where are the best neighborhoods to stay in Near West Side?
When considering your stay in Chicago, Illinois, exploring neighborhoods near West Side offers an ideal blend of accessibility and local charm. The area provides a convenient location for experiencing the city’s vibrant culture while enjoying the comfort of a private rental by owner. Whether you're seeking the bustling energy of urban life or quieter residential streets, Near West Side presents a variety of options to suit your preferences. Booking through Rent By Owner ensures a seamless, trustworthy experience, allowing you to focus on discovering all that this dynamic Chicago neighborhood has to offer.
Downtown Chicago
In the heart of the city, this area offers convenient access to major landmarks and a vibrant urban environment, making it ideal for travelers seeking proximity to Chicago's most iconic sights.
View 2291+ Rentals in Downtown ChicagoWest Loop
Known for its trendy dining scene and artistic vibe, the West Loop provides a lively neighborhood experience just minutes from downtown amenities.
View 218+ Rentals in West LoopPilsen
Immerse yourself in a culturally rich atmosphere with colorful murals and authentic cuisine, perfect for those looking to explore Chicago’s diverse local flavors.
View 3300+ Rentals in PilsenNorth Lawndale
This historic neighborhood offers a blend of community charm and urban renewal, providing an authentic Chicago experience with easy access to the region's cultural sites.
View 443+ Rentals in North LawndaleUniversity Village / Little Italy
Discover a neighborhood renowned for its Italian heritage, where traditional restaurants and local events create a welcoming environment close to the city's academic institutions.
View 103+ Rentals in University Village / Little ItalyIllinois Medical District
Home to top healthcare facilities and research centers, this district combines professional opportunities with convenient public transit options for visitors.
View 3502+ Rentals in Illinois Medical DistrictGreektown
Experience the vibrant Greek culture through authentic eateries and lively festivals, all within a walkable neighborhood that adds a unique flavor to your stay.
View 4320+ Rentals in GreektownHeart of Chicago
Centered around the city's bustling core, this area places you near premier attractions, shopping, and entertainment venues, ensuring an engaging visit in the region.
View 32+ Rentals in Heart of ChicagoBest Times to Visit Near West Side
When should you plan your Rentals by Owner stay?
Choosing the optimal time to visit here can greatly enhance your experience, as timing your trip within the region’s seasonal patterns allows for better planning and enjoyment of your rental by owner accommodations in Near West Side, Chicago.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you can enjoy the vibrant atmosphere and longer daylight hours in this area, making it ideal for exploring local amenities and events.
Fall (September to November)
Autumn brings milder weather and beautiful foliage, providing a pleasant setting to experience the region’s culture and outdoor activities.
Off-Season Highlights
Winter (December to February)
This quieter period offers a more relaxed atmosphere, perfect for those seeking less crowded accommodations while still enjoying the region’s indoor attractions.
Early Spring (March to April)
As the area transitions from winter, early spring provides fewer visitors and the chance to experience local life before peak tourism picks up again.
Weekly Weather Forecast for Near West Side
How to Book Your Near 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 Near 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
- Enjoy access to shared outdoor spaces such as courtyards or garden areas for relaxing or socializing.
- Benefit from on-site private patios or balconies that provide a personal outdoor retreat.
- Take advantage of nearby parks and green spaces perfect for walking, jogging, or picnicking in the area.
- Make use of outdoor grilling or barbecue facilities available at select rentals.
- Experience the convenience of secure bike storage for exploring the region on two wheels.
- Relax in outdoor seating areas designed for enjoying the fresh air and views of the surrounding cityscape.
- If available, enjoy resort-style amenities such as swimming pools with outdoor lounging zones within the vicinity.
Top Attractions Around Near West Side
What attractions are nearby?
Within this vibrant region, you can explore a variety of nearby activities that showcase the local culture and entertainment, making your stay both memorable and engaging.
Family Activities
- Field Museum of Natural History: Discover fascinating exhibits and interactive displays that will engage children and adults alike at this renowned museum in the region.
- Millennium Park: Enjoy outdoor art installations, open green spaces, and family-friendly events right in the heart of the city near the area’s vibrant attractions.
- Shedd Aquarium: Experience marine life up close with diverse aquatic exhibits that make for an educational and entertaining day out for your family.
- Chicago Cultural Center: Explore cultural exhibits, free performances, and engaging programs designed to inspire visitors of all ages here in this lively neighborhood.
Adult Activities
- Visit the United Center: Enjoy a thrilling game or concert at this iconic venue, immersing yourself in the local sports and entertainment scene.
- Explore the Illinois Medical District: Discover innovative medical facilities and research centers that highlight the area's contribution to healthcare and science.
- Stroll through Douglas Park: Relax with a walk or picnic in this expansive green space, offering a peaceful retreat amidst the city’s vibrant energy.
- Experience culinary delights at nearby restaurants: Savor diverse cuisines at popular dining spots known for authentic flavors and quality service within the region.
Other Places to Stay in Near West Side, IL
Near West Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's vibrant culinary scene by trying nearby restaurants to experience authentic flavors unique to the region.
- Plan Your Transportation: Use public transit or walk when possible to easily access popular attractions and make the most of your stay here without worrying about parking.
- Discover Nearby Cultural Spots: Incorporate visits to local galleries and theaters to immerse yourself in the neighborhood's creative spirit.
- Choose Strategic Accommodation Locations: Select a rental close to key transit hubs or attractions for convenient access and a more enjoyable experience in this part of the city.
Transportation Options
- CTA Transit: This regional transit service offers convenient bus and rail connections, making it easy to explore the city's attractions from your rental in the area.
- Chicago 'L' Train System: The nearby elevated train network provides quick access to downtown Chicago and beyond, ideal for travelers wanting efficient transportation options.
- Divvy Bikes: Bike-sharing services are readily available throughout the neighborhood, allowing you to enjoy scenic rides while discovering local highlights.
- Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft operate frequently here, offering reliable door-to-door transportation when needed.
Local Customs Options
- Respect for Local Art and Culture: You’ll find that embracing the area's vibrant art scene and cultural expressions enhances your experience here in the Near West Side.
- Supporting Small Businesses: It’s customary to patronize locally owned shops and eateries to truly connect with the community's authentic spirit.
- Celebration of Neighborhood Events: Participating in neighborhood festivals and public gatherings is a valued tradition that helps you engage more deeply with the region.
- Environmental Consciousness: Being mindful of sustainability practices, such as recycling and reducing waste, aligns with the community’s commitment to eco-friendly living in this area.
Frequently Asked Questions About Near West Side Rentals by Owner
1. What are the top vacation rentals in Near West Side?
There are a lot of options in Near West Side. If you plan on staying in the Near 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 Near 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
- Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
- Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
- Top Floor Views + Central Comfort
- Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural D
- The Neighborhood Hotel - Little Italy Two Bedroom
- Stylish 1BR in West Loop
- Stylish 2BR Retreat in Fulton Market for Getaways
2. How many Rentbyowner vacation rentals are available in Near West Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 451 in the Near 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 Near West Side.
3. What is the cancellation policy for a rental by owner in Near West Side, Chicago?
4. How do I communicate with the property owner in this area before booking?
5. Are there minimum stay requirements for rentals in this part of Chicago?
6. What amenities are typically included in rentals by owner near this region?
7. Is there a security deposit required when booking a rental here?
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