Discover Your Perfect Tri-Taylor Vacation Homes

Tri-Taylor Luxury Rentals

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8.0 (3 Reviews)
Apartment
The Upscale Getaway Near Downtown
  • Air Conditioner
  • Parking
  • Security/Safety
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Why Choose Rent By Owner for your Tri-Taylor 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 Tri-Taylor Vacation Rentals

Where are the best neighborhoods to stay in Tri-Taylor?

When exploring neighborhoods to stay in Tri-Taylor, Chicago, Illinois, you’ll find a vibrant community that offers easy access to many of the city’s top attractions. This area provides a comfortable and convenient location for those seeking an authentic Chicago experience. Whether you're looking for proximity to local amenities or a peaceful retreat within the city, staying in Tri-Taylor allows you to enjoy the best of what Chicago has to offer while benefiting from a welcoming neighborhood atmosphere. Booking your vacation rentals here ensures a seamless and reliable experience, making your trip memorable and stress-free.

Near West Side

This area offers a vibrant atmosphere with convenient access to the city's attractions, making it an ideal choice for travelers seeking a lively neighborhood with seamless transit options. Here, you can enjoy the energetic vibe while staying close to Chicago’s cultural and entertainment hubs.

View 330+ Rentals in Near West Side

North Lawndale

Located just west of the city center, this community provides a quieter environment with easy access to local parks and amenities. It’s a great spot to explore authentic Chicago living while enjoying the comfort of nearby transportation links.

View 443+ Rentals in North Lawndale

Illinois Medical District

Strategically situated in the heart of the region, this area is perfect for visitors wanting to stay close to medical facilities or academic institutions, offering convenience without sacrificing accessibility to downtown attractions. The neighborhood blends professional pursuits with easy transit connectivity.

View 3502+ Rentals in Illinois Medical District

Lawndale

This historic neighborhood provides an authentic Chicago experience with a welcoming community vibe, all within reach of the city’s major sites. It’s an excellent base for discovering the diverse culture and local flavor that the city has to offer.

View 435+ Rentals in Lawndale

Best Times to Visit Tri-Taylor

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience with the local climate and events, making your stay in Tri-Taylor, Chicago, Illinois, USA, truly memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May - June)

During these months, you can experience warm weather and lively city events, making it ideal for exploring the area’s cultural and outdoor attractions.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Early Fall (September - October)

This period offers pleasant temperatures and smaller crowds, providing a comfortable setting for sightseeing and enjoying local festivals in this vibrant destination.

Average Temperature Daytime: 70°F to 78°F - Nighttime: 55°F to 62°F

Off-Season Highlights

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Winter (December - February)

With colder temperatures and fewer visitors, this time allows you to find more affordable rates and a quieter atmosphere while still enjoying the city’s indoor attractions.

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

As temperatures gradually rise, this off-peak period provides a tranquil environment for exploring the region’s less crowded streets and cozy accommodations.

Average Temperature Daytime: 45°F to 58°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Tri-Taylor

How to Book Your Tri-Taylor 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 Tri-Taylor

More Top-Rated Vacation Rentals in Tri-Taylor 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 a private outdoor patio or balcony to relax and take in the fresh air.
  • Make use of shared garden spaces or courtyards available at many properties.
  • Take advantage of nearby parks or green areas ideal for picnics or outdoor activities.
  • Access outdoor seating areas perfect for dining al fresco with family or friends.
  • Benefit from on-site barbecue grills for outdoor cooking and gatherings.
  • Explore bicycle-friendly paths or bike rentals to discover the local neighborhood.
  • Utilize outdoor pools or splash areas often found at select vacation rentals in the region.

Top Attractions Around Tri-Taylor

What attractions are nearby?

Within the vibrant region, you can enjoy a variety of cultural experiences and outdoor activities that showcase the best of what this area has to offer, making it an ideal choice for your next getaway.

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Family Activities

  • Hugo Wolf Memorial Park: Enjoy family picnics and outdoor activities at this peaceful green space nestled within the neighborhood, perfect for relaxing after exploring the area.
  • Chicago History Museum in the Region: Discover engaging exhibits and interactive displays that bring local history to life, providing educational fun for children and adults alike.
  • Near West Side Playgrounds: Experience the community atmosphere and let the kids burn off energy at these well-maintained playgrounds close to your vacation rental.
  • Local Food Tours in the Area: Savor diverse culinary delights on guided family-friendly tours that showcase the region’s unique flavors and local eateries.
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Adult Activities

  • Explore the University of Illinois at Chicago Campus: Take a leisurely stroll through the vibrant grounds of this renowned university, soaking in the lively academic atmosphere right in the heart of the city.
  • Visit the Cook County Hospital Heritage Museum: Discover the rich medical history of the region with exhibits that highlight Chicago's pioneering healthcare achievements.
  • Enjoy Culinary Delights at Local Eateries: Savor diverse and authentic cuisines from nearby restaurants, offering a taste of the area's multicultural culinary scene.
  • Experience Cultural Events at Nearby Venues: Attend art exhibitions, live performances, or festivals held within easy reach, showcasing the region’s vibrant arts community.

Tri-Taylor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Cultural Spots: Take advantage of the area's diverse culinary scene and cultural venues to immerse yourself in the authentic local atmosphere during your stay.
  • Plan Convenient Transportation: Utilize nearby public transit options or walkable routes within the neighborhood to easily access iconic Chicago attractions without hassle.
  • Book Early for Popular Activities: Secure reservations ahead of time for popular restaurants and entertainment venues in this part of the city to ensure a smooth and enjoyable experience.
  • Choose Strategic Accommodation Locations: Select vacation rentals close to major transit lines or main streets to maximize your convenience and explore more efficiently here.

Transportation Options

  • Chicago Transit Authority (CTA) L Service: The CTA trains provide quick and reliable transportation connecting you to downtown Chicago and beyond within the area.
  • Bus Services: Local bus routes serve various neighborhoods and destinations, making getting around here convenient and budget-friendly.
  • Divvy Bike Share: Bike sharing stations offer an eco-friendly way to explore the region at your own pace and enjoy the scenic streets nearby.
  • Taxis and Rideshare Options: Rideshare services like Uber and Lyft operate extensively, providing flexible transportation directly from your vacation rentals to key points in this destination.

Local Customs Options

  • Respect for Local Cuisine: In this area, sharing traditional dishes and dining customs reflects the region’s rich culinary heritage and community spirit.
  • Celebration of Community Festivals: Participating in neighborhood festivals highlights the area's vibrant cultural traditions and strong social bonds.
  • Greeting Etiquette: Friendly nods or handshakes are common here, emphasizing the welcoming nature of the local residents.
  • Preservation of Historical Customs: Honoring age-old practices and storytelling maintains the unique character and history of this destination’s community.

Frequently Asked Questions About Tri-Taylor?

1. What are the top vacation rentals in Tri-Taylor?

There are a lot of options in Tri-Taylor. If you plan on staying in the Tri-Taylor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Tri-Taylor:

2. Which vacation homes in Tri-Taylor are best for families?

If you are looking for a family-friendly vacation home in Tri-Taylor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Tri-Taylor:

3. How many Rentbyowner vacation rentals are available in Tri-Taylor?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 53 in the Tri-Taylor 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 Tri-Taylor. 

4. What is the cancellation policy for vacation rentals in Tri-Taylor, Chicago?

Cancellation policies vary by listing. You should review the specific rental’s terms on the property page or contact the owner directly to understand the cancellation window and any applicable fees.

5. How do I ensure my booking in this area is secure and reliable?

Look for listings with verified owners and reviews from previous guests. The platform provides secure payment options and detailed host profiles to help you make a trustworthy reservation.

6. Are there any additional fees I should be aware of when booking vacation rentals in Chicago’s Tri-Taylor neighborhood?

Additional fees such as cleaning fees, service charges, or taxes are often outlined in the listing details. Always read the full description and contact the host for clarification before confirming your reservation.

7. What amenities can I expect in vacation rentals here?

Amenities vary but commonly include essentials like Wi-Fi, kitchen facilities, and laundry. Check each listing’s description for specific features and confirm with the owner if you have special requirements.

8. How close are these vacation rentals to local attractions and transportation in the region?

Many vacation rentals are conveniently located near public transit and key points of interest. Review the property location map and ask the host about nearby transportation options to plan your stay effectively.