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Discover Your Perfect West Town Rentals by Owner

West Town Rentals by Owner

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10.0 (5 Reviews)
Apartment
Speakeasy Serenity Retreat
  • Parking
  • Accessibility
  • Security/Safety
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10.0 (2 Reviews)
Apartment
Art Villa
  • Parking
  • Pet Friendly
  • View
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10.0 (1 Review)
Apartment
Modern River West 2BR with W&D by Zencity
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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More Top-Rated Rentals by Owner in West Town Area

Why Choose Rent By Owner for your West Town vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for West Town Rentals by Owner

Where are the best neighborhoods to stay in West Town?

Discover the vibrant neighborhoods of West Town, Chicago, Illinois, and find the perfect rental for your stay. Whether you’re seeking a lively atmosphere or a more relaxed vibe, this area offers diverse options that cater to your preferences. Staying in West Town means immersing yourself in a dynamic community with convenient access to local amenities and authentic Chicago experiences. With Rent By Owner, you can confidently book a trusted vacation rental, ensuring a seamless and dependable stay in this engaging neighborhood.

Downtown Chicago

Staying near the heart of the city offers easy access to major business and cultural hubs, making it an ideal choice for those who want to experience the vibrant energy of this destination. The area provides convenient proximity to key attractions and amenities that make your visit memorable.

View 1791+ Rentals in Downtown Chicago

River North

Known for its lively nightlife and art galleries, this neighborhood is perfect if you seek a dynamic atmosphere within reach of the region’s finest dining and entertainment options. Staying here places you at the center of contemporary Chicago while enjoying the comforts of a well-connected location.

View 484+ Rentals in River North

West Loop

This trendy district combines industrial charm with upscale eateries, making it a popular choice for travelers interested in experiencing the innovative culinary scene and vibrant arts culture of the area. Your stay here puts you close to both historic sights and modern attractions.

View 198+ Rentals in West Loop

Near North Side

Offering a mix of luxury accommodations and accessible public spaces, this part of the city appeals to visitors wanting a blend of sophistication and convenience. It's an excellent base for exploring the region’s premier shopping, dining, and entertainment venues.

View 818+ Rentals in Near North Side

Wicker Park

Renowned for its eclectic vibe and artistic community, this neighborhood invites you to enjoy unique boutiques, live music, and locally owned cafes. Staying here gives you a local perspective while remaining within easy reach of downtown attractions.

View 40+ Rentals in Wicker Park

Ukrainian Village

This historic enclave offers a charming atmosphere with rich cultural roots, ideal for travelers seeking a peaceful retreat with authentic local character. Its proximity to the region’s vibrant arts and food scenes enhances your overall experience.

View 3050+ Rentals in Ukrainian Village

River West

A thriving area known for its diverse dining options and innovative nightlife, the neighborhood appeals to those looking to immerse themselves in the creative spirit of the city. Staying here grants quick access to both urban excitement and scenic river views.

View 52+ Rentals in River West

East Village

This up-and-coming neighborhood features a laid-back atmosphere with a variety of independent shops and casual dining options, making it a comfortable base for exploring the region’s cultural offerings. Its friendly vibe complements the dynamic pace of the city.

View 144+ Rentals in East Village

Best Times to Visit West Town

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider scheduling your vacation during the times when local events and seasonal weather align with your preferences, ensuring a memorable experience in this vibrant area.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warmer weather and longer daylight hours, making it ideal for exploring outdoor attractions and local events.

Average Temperature Daytime: 80°F - 85°F - Nighttime: 65°F - 70°F
autumn
Fall (September to November)

The fall season offers pleasant temperatures and vibrant autumn foliage, providing a picturesque backdrop for your stay in this vibrant region.

Average Temperature Daytime: 65°F - 75°F - Nighttime: 50°F - 60°F

Off-Season Highlights

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Winter (December to February)

Visit during winter to experience fewer crowds and enjoy the cozy atmosphere, though you'll want to prepare for colder temperatures.

Average Temperature Daytime: 30°F - 40°F - Nighttime: 20°F - 30°F
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Spring (March to May)

Spring offers milder weather and blooming landscapes, making it a charming time to explore the area before the peak summer season begins.

Average Temperature Daytime: 50°F - 65°F - Nighttime: 35°F - 45°F

Weekly Weather Forecast for West Town

How to Book Your West Town vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in West Town

More Top-Rated Rentals by Owner in West Town Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 outdoor seating areas such as patios or decks to relax and take in the local surroundings.
  • Take advantage of private gardens or yards for outdoor leisure activities and gatherings.
  • Make the most of community green spaces or parks nearby for picnics or outdoor recreation.
  • Look for properties with outdoor grills or barbeque stations to enhance your cooking experience here.
  • Seek out rentals that offer bicycle storage or nearby bike paths to explore the area on two wheels.
  • Enjoy access to outdoor pools or hot tubs, perfect for unwinding after a day of exploring this vibrant region.
  • Utilize outdoor fireplaces or fire pits for cozy evenings outdoors during your stay here.

Top Attractions Around West Town

What attractions are nearby?

Within the area, you can enjoy a variety of activities that showcase the vibrant culture and local charm, making your stay here both exciting and memorable.

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Family Activities

  • Lincoln Park Zoo: Spend a day exploring this free zoo, where you can enjoy seeing a wide variety of animals right in the heart of the area.
  • Chicago History Museum: Immerse your family in the region's rich history through engaging exhibits and interactive displays suitable for all ages.
  • North Avenue Beach: Relax and play at this popular lakeside beach offering stunning views of Lake Michigan, perfect for picnicking and sandcastle building.
  • The 606 Trail: Take a family-friendly walk or bike ride along this elevated trail that showcases the local neighborhood's vibrant art and scenery.
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Adult Activities

  • Selling Your Artworks at Local Galleries: Explore the vibrant arts scene here by showcasing your work at renowned galleries that attract both locals and visitors alike.
  • Enjoying a Night Out at Trendy Bars and Restaurants: Discover the area's lively culinary scene with eclectic bars and restaurants that serve up innovative cuisine and craft cocktails.
  • Taking a Cultural Walking Tour: Immerse yourself in the neighborhood's history and architecture through guided tours that highlight its unique urban charm.
  • Attending Live Music or Theater Performances: Experience the region’s dynamic performing arts scene by catching live music shows or theatrical productions that cater to diverse tastes.

Other Places to Stay in West Town, IL

St. Stanislaus Kostka Church
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Chopin Theatre-Death and Harry Houdini
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House Theatre
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Touch of Jane Addams
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Polish Museum of America
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Ukrainian Village
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Smith Park
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East Village
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River West
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Wicker Park
Explore 40 Properties
Pulaski Park
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Noble Square
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West Town Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Neighborhoods: Take time to wander through the vibrant streets of this area to discover hidden gems and authentic eateries near your rental.
  • Plan Your Transportation: Utilize the region’s public transit options or consider walking to easily access popular attractions without the hassle of parking.
  • Book in Advance: Secure your rental early to enjoy a wider selection of owner-managed properties and ensure availability during busy seasons.
  • Engage with Hosts: Communicate directly with property owners for personalized recommendations and insider tips about the best spots nearby.

Transportation Options

  • CTA Bus Service: You can rely on the CTA bus network to navigate the area efficiently while exploring nearby neighborhoods and attractions.
  • Chicago Transit Authority (CTA) Trains: The local train system provides quick and convenient access across the city, making it easy to reach popular destinations from your rental.
  • Divvy Bike-Sharing Program: This eco-friendly transportation option allows you to explore the region at your own pace with easily accessible bike stations throughout the area.
  • Ride-Sharing Services: Popular options like Uber and Lyft offer flexible, door-to-door transportation, ideal for getting around comfortably during your stay here.

Local Customs Options

  • Local Art and Music Celebrations: Participate in the area's vibrant art and music festivals that showcase the region's creative spirit.
  • Neighborhood Dining Etiquette: Respect local dining customs by trying signature dishes and engaging with small, independently owned restaurants.
  • Historical Preservation Practices: Appreciate the effort to maintain historic buildings and landmarks that reflect this destination’s rich heritage.
  • Community Events and Markets: Engage with community markets and outdoor events that highlight the region’s cultural diversity and local craftsmanship.

Frequently Asked Questions About West Town Rentals by Owner

1. What are the top vacation rentals in West Town?

There are a lot of options in West Town. If you plan on staying in the West Town 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 Town:

2. How many Rentbyowner vacation rentals are available in West Town?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 451 in the West Town 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 Town. 

3. What is the cancellation policy for rental properties in West Town, Chicago?

The cancellation policies vary by individual owner and listing. To understand the specific terms, it’s best to review the cancellation details provided on the listing or contact the owner directly before booking.

4. How do I communicate with the owner of a rental in West Town during my stay?

Communication typically takes place through the messaging system on the booking platform. For any special requests or questions, reaching out directly to the owner via the platform ensures a smooth experience.

5. Are there any additional fees I should be aware of when booking a rental in the area?

Some listings may include extra charges such as cleaning fees or service fees. These details are usually outlined during the booking process, so please review the total price before confirming your reservation.

6. What amenities should I expect in a typical rental by owner in this destination?

Properties often feature essential amenities like Wi-Fi, kitchen facilities, and laundry options. For a complete list of amenities, refer to the specific listing details or contact the owner to confirm your needs.

7. Is there a minimum stay requirement for rentals in West Town, Chicago?

Minimum stay requirements can differ depending on the owner and property. Check the listing description or contact the owner directly to verify any specific stay duration before making a reservation.

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More Top-Rated Rentals by Owner in West Town Area