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Discover Your Perfect Chicago Resorts

Chicago Resorts

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8.6 (1376 Reviews)
Hotel
Sports Illustrated Resorts Chicago
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
View Availability
More Top-Rated Resorts in Chicago Area

Why Choose Rent By Owner for your Chicago 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 Chicago Resorts

Where are the best neighborhoods to stay in Chicago?

When visiting Chicago, Illinois, exploring neighborhoods like the Magnificent Mile offers you easy access to luxury shopping and vibrant city life, perfect for a lively getaway. If you prefer a more historic and artsy atmosphere, consider staying near Lincoln Park, where charming streets and cultural attractions provide a relaxing yet engaging experience. For those seeking an authentic local vibe combined with excellent dining options, the West Loop neighborhood is an ideal choice that captures the essence of Chicago's dynamic spirit.

Downtown Chicago

In the heart of the city, this area offers easy access to major business districts and vibrant entertainment options, making it ideal for travelers seeking convenience and excitement. Staying here places you close to iconic landmarks and a bustling urban atmosphere.

View 1548+ Rentals in Downtown Chicago

Magnificent Mile

Known for its luxury shopping, fine dining, and stunning architecture, this neighborhood provides a glamorous setting for visitors wanting to experience the best of the region. It’s perfect for those looking to indulge in urban sophistication near premier attractions.

View 3906+ Rentals in Magnificent Mile

The Loop

This central district is the cultural and commercial hub, offering convenient access to theaters, museums, and corporate offices. It's an excellent choice for travelers who want to immerse themselves in the city's dynamic downtown scene.

View 717+ Rentals in The Loop

River North

Famous for its vibrant arts scene and lively nightlife, this neighborhood boasts a mix of trendy galleries and upscale restaurants. It appeals to visitors seeking an energetic atmosphere within close proximity to downtown attractions.

View 332+ Rentals in River North

Hyde Park

Home to renowned universities and cultural institutions, this area's serene environment offers a unique blend of academic charm and historical significance. It’s perfect for guests interested in exploring the region’s intellectual and cultural heritage.

View 103+ Rentals in Hyde Park

Lincoln Park

Centered around a sprawling park and lush green spaces, the neighborhood delivers a peaceful retreat while still being close to city amenities. It’s an ideal spot for outdoor lovers and families seeking a relaxed yet accessible stay.

View 154+ Rentals in Lincoln Park

O'Hare

Conveniently located near one of the region's busiest airports, this area provides quick transit options for travelers on the go. It’s a practical choice for those prioritizing ease of travel during their visit.

View 50+ Rentals in O'Hare

Lakeview

Known for its vibrant community and diverse entertainment scene, this neighborhood offers a lively atmosphere with plenty of dining, nightlife, and recreational activities. It’s suitable for visitors looking to experience the local culture and lively urban lifestyle.

View 266+ Rentals in Lakeview

Best Times to Visit Chicago

When should you plan your Resorts stay?

Timing your visit to this vibrant destination can greatly enhance your experience, with the region offering ideal conditions during specific seasons when the weather is most favorable for exploring its renowned attractions and enjoying a relaxing stay at trusted resorts.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can expect warm weather and lively city events, making it an ideal time to enjoy outdoor activities in the area.

Average Temperature Daytime: high 80s to low 90s °F - Nighttime: low 60s to mid 70s °F
autumn
Autumn (September to November)

This season offers mild weather and beautiful fall foliage, perfect for exploring the region's scenic spots and enjoying the local cultural scene.

Average Temperature Daytime: mid 70s to low 80s °F - Nighttime: mid 50s to mid 60s °F

Off-Season Highlights

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Winter (December to February)

In winter, the area experiences colder temperatures and fewer tourists, providing a peaceful atmosphere for indoor pursuits and seasonal festivities.

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

Early spring sees gradually warming weather and blooming landscapes, offering a quieter time to explore the region's attractions before the summer rush begins.

Average Temperature Daytime: mid 50s to mid 60s °F - Nighttime: mid 30s to mid 40s °F

Weekly Weather Forecast for Chicago

How to Book Your Chicago 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 Chicago

More Top-Rated Resorts in Chicago 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

  • Enjoy outdoor swimming pools available at many resorts in the area, perfect for relaxing after exploring the city.
  • Take advantage of well-maintained community gardens and green spaces to unwind and connect with nature.
  • Experience outdoor grilling and picnic areas that make dining al fresco easy and enjoyable.
  • Stay active with access to tennis courts or basketball facilities on the property grounds.
  • Discover scenic walking and jogging paths that wind through the resort's outdoor spaces, offering picturesque views of the region.
  • Relax on private patios or balconies with seating areas to enjoy the fresh air and cityscape views.
  • Make use of outdoor fire pits or lounge areas ideal for social gatherings or quiet evenings under the stars.

Top Attractions Around Chicago

What attractions are nearby?

In this vibrant destination, you can enjoy a variety of activities nearby, including exploring world-class museums, strolling through scenic parks, and experiencing diverse culinary options-all conveniently accessible from your professional and dependable resort accommodation here.

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Family Activities

  • Shedd Aquarium: You can explore an impressive array of marine life and interactive exhibits perfect for engaging family members of all ages.
  • Millennium Park: Enjoy outdoor art installations, including the famous Cloud Gate sculpture, and participate in family-friendly events often hosted here.
  • Adler Planetarium: Discover fascinating space exhibits and enjoy breathtaking views of the city skyline, making it a great educational outing for your family.
  • Chicago Children's Museum: Located at Navy Pier, this museum offers hands-on activities and creative play spaces designed to entertain and inspire young visitors.
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Adult Activities

  • Architectural River Cruise: Experience a guided boat tour along the Chicago River to appreciate the city's iconic skyline and innovative architecture firsthand.
  • City Museum Exploration: Delve into the vibrant arts scene by visiting renowned galleries and exhibits that showcase local talent and contemporary works.
  • Fine Dining Experiences: Indulge in world-class cuisine at upscale restaurants offering diverse menus and views of the city’s bustling neighborhoods.
  • Spa and Wellness Centers: Relax and rejuvenate at luxury spas that provide restorative treatments, perfect after exploring the area's attractions.

Other Places to Stay in Chicago, IL

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Chicago Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit: Schedule your trip during the shoulder seasons to enjoy fewer crowds and better rates at local resorts in this vibrant area.
  • Explore Local Attractions: Take advantage of nearby cultural and entertainment venues that showcase the region’s unique heritage and modern appeal.
  • Utilize Public Transit: Use the city’s efficient transit system to easily access major sights and reduce travel hassle during your stay here.
  • Select the Ideal Accommodation: Choose a well-rated resort that offers convenient amenities and comfortable surroundings to enhance your visit in this destination.

Transportation Options

  • Chicago Transit Authority (CTA) Trains and Buses: You can rely on the extensive CTA network to easily navigate this vibrant city and reach your desired destination efficiently.
  • Divvy Bike Sharing System: For an active way to explore, the region offers a bike-sharing program that provides convenient access to bicycles for short trips around here.
  • Taxi and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available, offering flexible transportation tailored to your schedule in this area.
  • Car Rentals: Renting a vehicle gives you the freedom to discover nearby attractions and explore beyond the city with ease.

Local Customs Options

  • Greeting Etiquette: When visiting, you'll notice that locals often greet with a friendly nod or handshake, reflecting the region's warm and welcoming spirit.
  • Dining Customs: Sharing dishes family-style is common here, emphasizing community and togetherness during meals at local eateries.
  • Respect for Neighborhoods: It is customary to be mindful of noise levels and local decorum when exploring the diverse neighborhoods in the area.
  • Celebration Traditions: Attending seasonal parades and festivals highlights the area's vibrant cultural heritage and community pride.

Frequently Asked Questions About Chicago Resorts

1. How many Resorts are available in Chicago?

Currently, the total number of properties listed by RBO in 2026 is over 17 in the Chicago area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Chicago. 

2. What is the cancellation policy for resorts in this destination?

The cancellation policy varies depending on the specific resort you choose. You should review the cancellation terms listed on the booking page or contact the property owner directly for detailed information.

3. Are there any additional fees or charges when booking a resort here?

Additional fees, such as resort fees, cleaning charges, or taxes, are typically outlined during the booking process. It's advisable to read the full listing details or contact the owner for clarification.

4. How do I know if my reservation is confirmed and secure?

Reservation confirmation is provided once your booking is successfully completed and payment is processed. For added security, verify the confirmation email and contact the property owner if you have any concerns.

5. Can I make special requests or customize my stay at a resort in this region?

Many resorts accommodate special requests, but these depend on availability and the property's policies. To ensure your needs are met, communicate your preferences directly with the property owner before finalizing your reservation.

6. What amenities are included with the resort booking?

Amenities vary by property but typically include essentials such as Wi-Fi, parking, and access to recreational facilities. Check the individual listing for a detailed list of what's included or contact the owner for specific inquiries.

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More Top-Rated Resorts in Chicago Area