Discover Your Perfect The Loop Resorts

The Loop Resorts

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8.6 (1378 Reviews)
Hotel
Sports Illustrated Resorts Chicago
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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More Top-Rated Resorts in The Loop Area

Why Choose Rent By Owner for your The Loop Resorts?

What makes our Resorts 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 The Loop Resorts

Where are the best neighborhoods to stay in The Loop?

Staying in the The Loop neighborhood offers you convenient access to Chicago's vibrant downtown area, making it ideal for exploring cultural landmarks and city attractions. This central location provides a perfect base for experiencing the energy of Chicago while enjoying comfortable surroundings. When booking your stay, consider accommodations in this lively district for easy transportation and proximity to major highlights.

Downtown Chicago

Staying in this vibrant area places you at the heart of the city’s most iconic attractions and bustling commercial district, offering easy access to premier resorts. It’s the perfect choice for travelers seeking a central location with unparalleled convenience.

View 1539+ Rentals in Downtown Chicago

River North

Known for its lively art scene and upscale dining options, this neighborhood provides an ideal setting for visitors looking to enjoy a chic and energetic atmosphere close to high-quality resorts. The region combines modern urban appeal with excellent connectivity.

View 326+ Rentals in River North

South Loop

This dynamic neighborhood offers proximity to cultural institutions and scenic parks, making it a desirable spot to stay while exploring the city’s vibrant lifestyle from comfortable resorts nearby. It’s well-suited for those wanting a blend of relaxation and city adventures.

View 369+ Rentals in South Loop

West Loop

Famous for its trendy eateries and historic industrial architecture, this area is ideal for guests who appreciate a hip, modern vibe along with easy access to top resorts and local hotspots. It’s a great base for experiencing Chicago’s culinary scene.

View 221+ Rentals in West Loop

Near North Side

Offering proximity to lakeside parks and upscale shopping, this neighborhood is a prime choice for travelers who desire a combination of scenic views and luxury resorts. Here, comfort and style come together seamlessly.

View 613+ Rentals in Near North Side

Lakeshore East

Nestled along the waterfront, this area boasts modern residential spaces and resort-style amenities, perfect for visitors seeking tranquility with convenient access to downtown attractions. It’s an excellent peaceful retreat within the city.

View 3659+ Rentals in Lakeshore East

Near East Side

This neighborhood features contemporary developments and easy access to major transportation routes, making it a practical choice for travelers aiming to stay close to stylish resorts and the region’s sights. Its strategic location enhances your visit.

View 735+ Rentals in Near East Side

Printers Row

With its historic charm and literary roots, this locale offers a unique ambiance for those wanting a distinctive experience near boutique resorts. It’s ideal for guests looking to immerse themselves in Chicago’s creative spirit.

View 3802+ Rentals in Printers Row

Best Times to Visit The Loop

When should you plan your Resorts stay?

To make the most of your stay, consider visiting during off-peak seasons when this destination offers fewer crowds and better deals, allowing you to enjoy the area’s vibrant atmosphere and attractions at a more relaxed pace.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, you'll experience warm weather ideal for exploring the vibrant city life and enjoying outdoor activities. This is when demand for accommodations in Chicago's downtown area, including nearby resorts, is at its highest.

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

Autumn brings mild temperatures and colorful scenery, making it a popular time for visitors seeking pleasant weather and cultural events. The region’s resorts tend to be busier during these months as travelers take advantage of the comfortable climate.

Average Temperature Daytime: - Nighttime:

Off-Season Highlights

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Winter (December to February)

In the winter months, the area quiets down, offering a more tranquil experience and often better rates on resorts. The cold weather attracts fewer tourists, making it an ideal time for those seeking a peaceful retreat.

Average Temperature Daytime: around 35°F - Nighttime: near 20°F
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Early Spring (March to May)

As the region transitions into spring, you’ll find less crowding and more affordable resort options. The weather gradually warms, providing a comfortable environment to enjoy the city's sights without the peak season crowds.

Average Temperature Daytime: - Nighttime:

Weekly Weather Forecast for The Loop

How to Book Your The Loop Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. 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 The Loop

More Top-Rated Resorts in The Loop Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts 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

  • Access to scenic outdoor lounge areas where you can relax and take in the city views.
  • Enjoyable outdoor seating and dining spaces perfect for al fresco meals or social gatherings.
  • Well-maintained walking or jogging paths for outdoor exercise amidst urban scenery.
  • Beautifully landscaped gardens that offer a peaceful retreat within the bustling city center.
  • Modern community BBQ grills for outdoor cooking and casual get-togethers.
  • Patio or terrace areas ideal for reading, sunbathing, or simply unwinding after exploring nearby attractions.
  • Outdoor swimming pools or rooftop decks to enjoy the region's pleasant weather during your stay.

Top Attractions Around The Loop

What attractions are nearby?

In this vibrant part of Chicago, you can explore a variety of nearby activities such as cultural museums, iconic landmarks, and diverse dining options that showcase the city's rich history and modern flair.

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Family Activities

  • Millennium Park: You can explore this iconic park that offers engaging outdoor art installations and family-friendly activities right in the heart of the city.
  • Chicago Children's Museum: Located at Navy Pier, this museum provides hands-on exhibits and interactive learning experiences tailored for children of all ages.
  • Shedd Aquarium: Discover a diverse array of marine life and enjoy captivating shows that make it a perfect day out for families seeking an educational adventure.
  • Adler Planetarium: Engage with space displays and enjoy stunning skyline views as you explore the wonders of our universe together as a family.
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Adult Activities

  • Architectural River Cruise: Experience stunning views of the city’s iconic skyline on a guided boat tour along the Chicago River, offering both relaxation and captivating scenery.
  • Art Institute of Chicago: Explore world-class art collections and exhibitions at one of the most renowned cultural institutions in the region, perfect for enriching your visit.
  • Millennium Park: Enjoy a leisurely stroll or outdoor activities amidst contemporary art installations and beautifully landscaped gardens in this must-visit urban space.
  • Theatre District: Catch a captivating live performance or musical in the vibrant theatre scene that celebrates the area's rich entertainment heritage.

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The Loop Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit Strategically: Schedule your activities to make the most of the vibrant urban scene while allowing time to explore nearby attractions and enjoy local events in the area.
  • Utilize Public Transportation: Take advantage of the extensive transit options to conveniently navigate the region, saving time and avoiding parking hassles during your stay.
  • Explore Local Dining: Indulge in the area's diverse culinary scene by seeking out popular restaurants and cafes that showcase the region's unique flavors.
  • Book Nearby Activities Early: Secure reservations or tickets for popular tours and experiences ahead of time to ensure availability and maximize your visit here.

Transportation Options

  • Chicago Transit Authority (CTA) L System: Conveniently connect to various parts of the city through the extensive elevated and subway train network, making it easy to explore this vibrant destination.
  • Bus Services: Local buses operated by the CTA provide flexible options for getting around the area, offering routes that reach many popular neighborhoods and attractions.
  • Taxis and Rideshare Services: Professional taxi and rideshare options like Uber and Lyft offer door-to-door transportation within this hub of activity, ensuring a quick and comfortable journey.
  • Bike-Sharing Programs: Public bike-share systems allow you to enjoy scenic rides across this urban region, perfect for those seeking an eco-friendly and active way to see the sights.

Local Customs Options

  • Greektown Customs: Embrace the area's rich Greek heritage by participating in local festivals and dining at authentic Greek restaurants that celebrate this vibrant culture.
  • Jazz Tradition: Experience the deep-rooted jazz history here by visiting live music venues that showcase the region's influential musical legacy.
  • Architectural Appreciation: Appreciate the unique architectural styles that define this destination, with many tours highlighting the historic and modern structures that line the city streets.
  • Foodie Culture: Indulge in the local culinary customs by trying signature dishes at established eateries, reflecting the diverse food scene that makes this area a culinary hub.

Frequently Asked Questions About The Loop Resorts

1. What are the top Resorts in The Loop?

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

2. How many Resorts are available in The Loop?

Currently, the total number of properties listed by RBO in 2026 is over 26 in the The Loop area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in The Loop. 

3. What is the cancellation policy for resorts in this area?

The cancellation policy varies between properties; please review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

4. Are there any additional fees I should be aware of when booking a resort here?

Additional fees, such as resort fees, cleaning charges, or taxes, are typically outlined on the property listing. To ensure clarity, check the detailed description or reach out to the host before completing your reservation.

5. What amenities are generally included with resorts in this destination?

Resorts often offer amenities like Wi-Fi, fitness centers, pools, and on-site dining. For exact amenities available at your chosen property, refer to the listing details or contact the owner directly.

6. Is it possible to request special accommodations or upgrades for my stay?

Many resorts accommodate special requests such as room upgrades or accessibility needs. Contact the property owner beforehand to discuss any specific requirements to enhance your experience.

7. How do I secure the best rates for a stay at a resort in this region?

To find competitive rates, consider booking in advance, checking for promotional offers, or reaching out directly to the owner for any current discounts or packages.

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