Discover Your Perfect Near West Side Vacation Homes

Near West Side Luxury Rentals

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Near West Side Pet Friendly Vacation Rentals

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Near West Side Large Vacation Homes

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Why Choose Rent By Owner for your Near West Side Vacation Rental Homes?

What makes our Vacation Rentals 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 Near West Side Vacation Rentals

Where are the best neighborhoods to stay in Near West Side?

When exploring neighborhoods to stay in near West Side, Chicago, Illinois, you’ll find a vibrant area rich in history and culture. This location offers convenient access to some of the city’s most exciting attractions, making it an ideal choice for travelers seeking an authentic Chicago experience. Whether you're looking for lively surroundings or a quieter retreat, the neighborhood provides a variety of vacation rentals that cater to your preferences. Booking your stay here ensures you’re well-positioned to enjoy all that the West Side has to offer, with seamless and reliable accommodation options that make your trip memorable and stress-free.

Downtown Chicago

The heart of the city offers easy access to iconic landmarks and vibrant urban life, making it an ideal choice for those seeking the lively pace of downtown. Staying here places you in close proximity to premier dining, shopping, and cultural experiences throughout the region.

View 1791+ Rentals in Downtown Chicago

West Loop

Known for its trendy restaurants and modern ambiance, this neighborhood offers a dynamic atmosphere perfect for exploring the culinary scene while enjoying convenient access to the nearby attractions of the area. It’s an excellent base for travelers looking to experience Chicago's innovative spirit.

View 198+ Rentals in West Loop

Pilsen

Rich in cultural heritage and artistic expression, this neighborhood invites you to immerse yourself in vibrant murals, local galleries, and authentic cuisine. Choosing accommodations here grants a unique perspective of the city's diverse community.

View 3300+ Rentals in Pilsen

North Lawndale

This historically significant area offers a quieter, more residential setting with easy access to transportation routes. Staying here provides an authentic experience of the local lifestyle while remaining connected to the broader city.

View 443+ Rentals in North Lawndale

University Village / Little Italy

Boasting a charming blend of academic influence and Italian heritage, this neighborhood is perfect for visitors seeking cultural richness and flavorful cuisine. Your stay here places you near educational institutions and lively neighborhood festivals.

View 89+ Rentals in University Village / Little Italy

Illinois Medical District

A hub for healthcare and innovation, this district combines practical accessibility with proximity to some of the city's key medical facilities. It's a strategic location for those traveling for work or medical purposes.

View 3502+ Rentals in Illinois Medical District

Greektown

Famous for its authentic Greek eateries and lively atmosphere, staying here offers a taste of Mediterranean culture right in the city. It’s an ideal neighborhood for food enthusiasts and nightlife seekers alike.

View 4320+ Rentals in Greektown

Heart of Chicago

Centered in the city's core, this area offers unmatched convenience to major attractions, entertainment venues, and public transit. It’s the perfect place to stay if you want to experience everything the city has to offer from a central location.

View 27+ Rentals in Heart of Chicago

Best Times to Visit Near West Side

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as seasonal variations in this destination influence everything from weather to local events, making it important to consider when planning your stay in the area.

Peak Season Highlights

summer
Summer (June - August)

During the warm summer months, this destination experiences high visitor traffic, making it an ideal time to explore popular attractions and enjoy outdoor activities.

Average Temperature Daytime: around 85°F - Nighttime: about 70°F
autumn
Fall (September - November)

The vibrant fall foliage and pleasant weather attract visitors seeking a quieter yet lively atmosphere in the region.

Average Temperature Daytime: roughly 75°F - Nighttime: around 55°F

Off-Season Highlights

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Winter (December - February)

The colder winter months bring fewer tourists, offering a more peaceful experience and better opportunities for budget-friendly bookings.

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

Early spring sees fewer visitors, with mild temperatures and blooming scenery providing a serene setting for your visit.

Average Temperature Daytime: around 60°F - Nighttime: about 45°F

Weekly Weather Forecast for Near West Side

How to Book Your Near West Side Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Near West Side

More Top-Rated Vacation Rentals in Near West Side Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 private patios or balconies where you can relax and take in the surroundings.
  • Benefit from access to communal gardens or green spaces, perfect for outdoor gatherings or leisurely strolls.
  • Take advantage of on-site grilling facilities to prepare meals outdoors during your stay.
  • Make the most of nearby parks or open areas ideal for outdoor activities like jogging, biking, or picnicking.
  • Experience secure, dedicated parking spaces that allow easy outdoor vehicle management.
  • If available, utilize outdoor fitness zones or sport courts located within the property grounds.
  • Discover scenic walking paths or bike trails conveniently accessible from the accommodation for exploring the area.

Top Attractions Around Near West Side

What attractions are nearby?

Within this vibrant neighborhood, you can enjoy a variety of activities ranging from exploring cultural landmarks to visiting entertainment venues, all conveniently accessible during your stay in the area.

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Family Activities

  • Lincoln Park Zoo: Enjoy a day exploring one of the oldest zoos in the country, perfect for family members of all ages seeking wildlife encounters close to here.
  • Millennium Park: Experience outdoor art installations and open spaces where your family can relax, take photos, and enjoy free public concerts in the nearby region.
  • The Chicago Children's Museum: Engage with interactive exhibits designed for young explorers, offering educational fun just a short distance from your accommodation.
  • Shedd Aquarium: Discover marine life through immersive exhibits and live shows that make for an exciting family outing near this destination.
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Adult Activities

  • Explore the United Center: Experience world-class sports and entertainment events in this iconic venue, right at your doorstep during your stay.
  • Visit the Whitney M. Young Jr. Pool: Relax and unwind by enjoying recreational swimming sessions at this popular community pool close to your accommodation.
  • Discover local art at the Chicago Innovative Design Studio: Engage with contemporary artworks and participate in creative workshops within this vibrant art space nearby.
  • Enjoy the culinary scene at nearby restaurants: Savor diverse dining options that showcase the region’s unique flavors, perfect for food enthusiasts exploring here.

Other Places to Stay in Near West Side, IL

Mars Gallery
Mars Gallery Vacation Rentals
Fulton Market
Fulton Market Vacation Rentals
Packer Schopf Gallery
Packer Schopf Gallery Vacation Rentals
Union Park
Union Park Vacation Rentals
threewalls
threewalls Vacation Rentals
Pitchfork Music Festival
Pitchfork Music Festival Vacation Rentals
Greektown
Greektown Vacation Rentals
Illinois Medical District
Illinois Medical District Vacation Rentals
West Loop
West Loop Vacation Rentals
University Village / Little Italy
University Village / Little Italy Vacation Rentals
Tri-Taylor
Tri-Taylor Vacation Rentals
West Loop Gate
West Loop Gate Vacation Rentals
More Places to Stay Near Near West Side

Near West Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the unique cultural and entertainment venues in the area to enrich your stay and discover more about this vibrant destination.
  • Plan Your Transportation: Familiarize yourself with public transit options or nearby bike rentals to conveniently navigate the region without stress.
  • Check Out Dining Options: Savor the diverse culinary scene by exploring popular eateries, ensuring you experience the flavors that make this neighborhood special.
  • Book in Advance: Secure your vacation rentals early to access the best selection of comfortable accommodations close to key attractions here.

Transportation Options

  • Chicago Transit Authority (CTA) L System: The extensive train and bus network offers you convenient access to the city's key attractions right from your vacation rental in the area.
  • Divvy Bike Sharing: With bike stations scattered throughout this destination, you can explore the neighborhood at your own pace using the city's popular bike-sharing service.
  • Metra Commuter Rail: For easy day trips outside the city, the Metra trains connect nearby suburbs and provide reliable transportation options.
  • Taxi and Rideshare Services: Uber, Lyft, and local taxi services are readily available here, offering flexible transportation at any time of day or night.

Local Customs Options

  • Deep-Dish Pizza Tradition: Embrace the local custom of enjoying hearty deep-dish pizza, a signature culinary experience you can find in many eateries here.
  • Jazz Music Appreciation: Experience the area’s rich jazz heritage by visiting venues that celebrate this soulful musical tradition prevalent in the region.
  • Street Art and Murals: Discover the vibrant street art scene that reflects the area's cultural diversity and creative spirit, often showcased in accessible outdoor spaces.
  • Indigenous and Local Celebrations: Participate in community festivals and events that highlight the region's historical roots and diverse cultural expressions.

Frequently Asked Questions About Near West Side?

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:

2. How many vacation rentals have private pools in Near West Side?

There are 6 vacation rentals with private pools near Near West Side. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Near West Side are best for families?

If you are looking for a family-friendly vacation home in Near 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 Near West Side:

4. 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 515 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. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the specific listing. It is recommended to review the cancellation details listed on the property page or contact the owner directly for the most accurate information.

6. How do I confirm my booking in this region?

You can secure your reservation by completing the booking process on the listing page, where you'll find detailed instructions. It's always best to verify your booking confirmation with the property owner if you have any questions.

7. Are there any house rules I should be aware of before booking?

House rules are typically provided within the property listing. To ensure a smooth stay, read these rules carefully and reach out to the host if you need clarification about any specific policies.

8. Is there availability during my preferred dates in this destination?

Availability depends on current bookings. You can check real-time availability directly through the listing, or contact the owner for further assistance to ensure your preferred dates are open.

9. What amenities are included with vacation rentals in this part of the city?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. Review the listing details thoroughly or ask the owner for specifics to make sure all your needs are met during your stay.

Near West Side Top Rated Vacation Rentals

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9.4 (715 Reviews)
Hotel
Nobu Hotel Chicago
  • Air Conditioner
  • Parking
  • Pool
View Availability
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