Discover Your Perfect West Loop Vacation Homes

West Loop Luxury Rentals

See More West Loop Luxury Vacation Rentals
Find More West Loop Villas, Resorts, & Rentals on BedroomVillas

West Loop Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in West Loop on PetFriendly.io

West Loop Large Vacation Homes

See More Family Vacation Rentals in West Loop on FVR

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

What makes our Vacation Rentals special?

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

Popular Areas for West Loop Vacation Rentals

Where are the best neighborhoods to stay in West Loop?

When choosing where to stay in Chicago, the West Loop neighborhood offers an ideal blend of vibrant city life and convenient access to key attractions. This dynamic area is known for its modern urban atmosphere, making it a popular choice for travelers seeking an authentic Chicago experience. Staying in the West Loop means you’ll be close to trendy dining spots, cultural venues, and easily accessible transportation options. Whether you're looking for stylish apartments or comfortable homes, this neighborhood provides a range of vacation rentals that combine comfort with the convenience of city living. Experience the best of Chicago from your home base in West Loop, where vibrant energy and lively neighborhoods create the perfect setting for your trip.

Downtown Chicago

This bustling area offers convenient access to many of the city's key attractions, making it an ideal choice for visitors seeking to explore the vibrant urban landscape from their vacation rentals. Staying here places you close to major business districts and entertainment options within the region.

View 1791+ Rentals in Downtown Chicago

The Loop

Known as Chicago's cultural and commercial heart, this neighborhood provides a dynamic backdrop for your stay, with easy access to renowned theaters, museums, and parks. Your vacation rentals here offer a perfect base to immerse yourself in the city's lively atmosphere.

View 775+ Rentals in The Loop

River North

Famous for its thriving arts scene and vibrant nightlife, this district is ideal for those wanting to experience Chicago’s creative energy from their vacation rentals. The area's trendy restaurants and galleries make it a popular spot for exploring local culture.

View 484+ Rentals in River North

Near North Side

Offering a blend of luxury accommodations and scenic views, this neighborhood is perfect for travelers looking for upscale vacation rentals within close reach of major city attractions. It provides a sophisticated setting for exploring the region's prominent landmarks.

View 818+ Rentals in Near North Side

Chinatown

Rich in cultural heritage, this area features diverse dining and shopping options, making it a unique place to stay while discovering authentic local traditions. Vacation rentals here serve as a peaceful retreat amid the vibrant community life.

View 3053+ Rentals in Chinatown

Near West Side

This diverse neighborhood offers a mix of historic charm and modern development, giving you a well-rounded experience during your stay. Its proximity to various attractions makes it a practical choice for travelers exploring the city.

View 331+ Rentals in Near West Side

West Town

Known for its eclectic character and vibrant neighborhoods, this area provides a variety of stylish vacation rentals that enable you to enjoy the region’s artistic and cultural offerings firsthand. It’s an inviting place to experience local life.

View 283+ Rentals in West Town

University Village / Little Italy

Boasting a rich academic and culinary heritage, this neighborhood makes an excellent base for those interested in exploring the region’s educational institutions and authentic Italian cuisine. Vacation rentals here offer a cozy, culturally immersive experience.

View 89+ Rentals in University Village / Little Italy

Best Times to Visit West Loop

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you make the most of your stay in this vibrant destination, allowing you to experience its unique charm and enjoy your preferred vacation rentals in West Loop, Chicago.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll experience the peak of the area’s lively atmosphere, making it ideal for exploring all that the region offers.

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

The early fall offers pleasant weather and vibrant cityscapes, attracting visitors who want to enjoy outdoor activities and local events.

Average Temperature Daytime: about 70°F to 75°F - Nighttime: 55°F to 60°F

Off-Season Highlights

image
Winter (December to February)

The colder months bring fewer tourists, providing a quieter experience, perfect for those seeking a more relaxed visit with lower accommodation costs.

Average Temperature Daytime: around 30°F to 40°F - Nighttime: 20°F to 30°F
image
Early Spring (March to April)

As the city begins to thaw, you can enjoy less crowded attractions and better deals, though the weather may still be unpredictable.

Average Temperature Daytime: about 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for West Loop

How to Book Your West Loop 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 West Loop

More Top-Rated Vacation Rentals in West Loop 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 access to a private outdoor patio or balcony to relax outdoors in the heart of the city.
  • Take advantage of communal rooftop terraces offering panoramic views of the Chicago skyline.
  • Benefit from on-site outdoor parking for convenient and secure vehicle storage.
  • Access landscaped courtyards or garden areas designed for outdoor leisure and gatherings.
  • Make use of outdoor grilling stations available within shared outdoor spaces.
  • Explore nearby parks or green spaces that are easily accessible from your rental here.
  • Utilize outdoor fitness setups or designated walking paths integrated into the property amenities.

Top Attractions Around West Loop

What attractions are nearby?

In this vibrant area, you can explore a variety of dining options, enjoy nearby art galleries, and experience live entertainment, all within easy reach from your vacation rentals in West Loop, Chicago.

image
image

Family Activities

  • Children's Museum Chicago: Engage the whole family with interactive exhibits and hands-on activities designed to spark creativity in this renowned museum just a short drive from your accommodation.
  • Downtown Riverwalk: Take a leisurely stroll along the scenic riverfront where families can enjoy views of the city skyline, boat tours, and outdoor spaces perfect for picnics.
  • Ping Tom Memorial Park: Relax and play in this waterfront park featuring playgrounds, open green spaces, and breathtaking views of the Chicago River, ideal for family outings.
  • Perseverance Park: Discover this family-friendly park nestled in the heart of downtown that offers open areas for games and space for children to explore safely while soaking in the vibrant city atmosphere.
image

Adult Activities

  • Dining Experience: Indulge in the renowned culinary scene with a visit to some of the area's best restaurants offering diverse and innovative cuisines.
  • Art Galleries and Exhibitions: Explore vibrant art galleries showcasing contemporary masterpieces that highlight the region’s thriving creative community.
  • Nightlife Adventures: Enjoy lively bars and music venues where you can experience the dynamic nightlife that makes this destination unique.
  • Fitness and Wellness Centers: Take advantage of upscale gyms and wellness studios to relax and stay active during your stay here.

Other Places to Stay in West Loop, 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
Mary Bartelme Park
Mary Bartelme Park Vacation Rentals
Batcolumn
Batcolumn Vacation Rentals
Greektown
Greektown Vacation Rentals
Old St Patrick’s Church
Old St Patrick’s Church Vacation Rentals
Union Station
Union Station Vacation Rentals
West Loop Gate
West Loop Gate Vacation Rentals
More Places to Stay Near West Loop

West Loop Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the vibrant culinary scene right here by seeking out neighborhood eateries and cafes to enjoy authentic regional flavors.
  • Plan Your Transportation: Utilize nearby public transit or consider walking to easily access popular spots in this destination without the hassle of parking.
  • Discover Unique Neighborhoods: Use your stay as an opportunity to explore surrounding areas, each offering its own character and hidden gems that truly showcase the region’s diversity.
  • Attend Area Events: Check local schedules for events or markets happening nearby to immerse yourself in the culture and make your visit memorable.

Transportation Options

  • Chicago Transit Authority (CTA) Trains: You can easily access the city's downtown and beyond via the CTA train system, with nearby stations connecting you to key areas throughout the region.
  • Bus Services: Local bus routes serve this neighborhood well, offering a convenient way to explore the city without needing to rent a car.
  • Divvy Bike Share: The area is well-connected with bike-sharing stations, allowing you to enjoy scenic rides and quick trips within the city’s vibrant neighborhoods.
  • Taxi and Rideshare Services: Taxis and popular ride-sharing options provide on-demand transportation for comfortable, door-to-door travel here in the city center.

Local Customs Options

  • Chicago-style Deep Dish Pizza: You’ll find that sharing a slice of this iconic pizza is a cherished local tradition here in the region.
  • First Fridays Art Walks: Participating in the monthly art events is a wonderful way to experience the vibrant creative scene of this destination.
  • Foodie Culture and Farm-to-Table Dining: Embracing locally sourced ingredients, residents and visitors alike enjoy the region’s emphasis on fresh, innovative cuisine.
  • Celebration of Architectural Heritage: Appreciating the area's renowned modern and historic architecture deepens your connection with the unique character of this locale.

Frequently Asked Questions About West Loop?

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

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

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

There are 4 vacation rentals with private pools near West Loop. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in West Loop, 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 Loop:

4. How many Rentbyowner vacation rentals are available in West Loop?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 265 in the West Loop 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 Loop. 

5. What is the cancellation policy for vacation rentals in West Loop, Chicago?

Cancellation policies vary by listing; you should review the specific property details or contact the property owner directly to understand the applicable refund and cancellation terms.

6. How do I find out if a rental in this area allows pets?

Pet policies depend on each individual property; please check the listing details or reach out to the host for information on pet allowances and any associated fees.

7. Are there specific check-in and check-out times I should be aware of when booking in this destination?

Check-in and check-out times are set by each property owner; consult the listing or communicate with the host to confirm your arrival and departure schedule.

8. What amenities are typically included in vacation rentals here?

Amenities vary between properties but often include essentials like Wi-Fi, kitchen facilities, and laundry options. For specifics, see the detailed listing or contact the owner directly.

9. Is there a minimum stay requirement for booking here?

Minimum stay policies differ among listings; please review the property description or contact the owner to confirm any stay length restrictions.