Discover Your Perfect Chicago Vacation Homes

Chicago Pet Friendly Vacation Rentals

10.0 (6 Reviews)
House
Stunning home in Skokie
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Chicago 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 Chicago Vacation Rentals

Where are the best neighborhoods to stay in Chicago?

Discover the diverse neighborhoods to stay in Chicago, Illinois, each offering a unique atmosphere and convenient access to the city’s top attractions. Whether you're looking for the vibrant energy of downtown Chicago or the historic charm of surrounding districts, you'll find that choosing the right neighborhood enhances your overall experience. From trendy areas filled with local eateries and boutique shops to more relaxed communities perfect for exploring on foot, Chicago's neighborhoods provide an ideal setting for your vacation rental stay. Trust in reliable vacation rentals that make your booking process seamless, ensuring you enjoy a comfortable and memorable visit to this dynamic city.

Downtown Chicago

Stay in the heart of the city where you'll find easy access to cultural attractions, dining, and entertainment. This area offers a vibrant urban environment perfect for exploring the region's dynamic atmosphere.

View 1791+ Rentals in Downtown Chicago

Magnificent Mile

This renowned shopping district combines luxury retail, upscale restaurants, and stunning architecture, making it an ideal choice for those seeking a lively and stylish stay in the region.

View 4128+ Rentals in Magnificent Mile

The Loop

Located at the core of the city’s business and arts districts, this neighborhood provides convenient access to theaters, museums, and major transportation hubs for effortless exploration.

View 775+ Rentals in The Loop

River North

Known for its thriving art galleries, trendy restaurants, and modern lofts, this dynamic neighborhood offers an energetic vibe close to the city’s entertainment options.

View 484+ Rentals in River North

Hyde Park

This culturally rich area is perfect for visitors interested in academic institutions and historical sites, offering a tranquil escape with easy city access.

View 84+ Rentals in Hyde Park

Lincoln Park

Famous for its scenic park and vibrant neighborhood scene, this area combines outdoor beauty with boutique shopping and diverse dining options.

View 143+ Rentals in Lincoln Park

O'Hare

Conveniently situated near the major airport, staying here allows for easy travel connections and quick access to the city's attractions.

View 66+ Rentals in O'Hare

Lakeview

A lively neighborhood known for its nightlife, lakeside parks, and eclectic vibe, perfect for travelers looking for energetic entertainment and outdoor activities.

View 236+ Rentals in Lakeview

Best Times to Visit Chicago

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here ensures you can fully enjoy the local atmosphere and events, making your stay in Chicago's vibrant area truly memorable.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather and vibrant outdoor events, making it an ideal time for exploring the city’s attractions.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 65°F (18°C)
autumn
Fall (September to November)

Autumn brings crisp air and colorful foliage, creating a picturesque setting that enhances your visit to this destination during its most lively season.

Average Temperature Daytime: approximately 70°F (21°C) - Nighttime: roughly 50°F (10°C)

Off-Season Highlights

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Winter (December to February)

The winter months feature cold weather and fewer crowds, offering a quieter experience while still allowing you to enjoy indoor cultural venues.

Average Temperature Daytime: around 35°F (2°C) - Nighttime: close to 20°F (-6°C)
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Early Spring (March to April)

In early spring, the region begins to awaken with milder weather and fewer visitors, providing a peaceful time to explore without the peak-season crowds.

Average Temperature Daytime: about 50°F (10°C) - Nighttime: roughly 35°F (2°C)

Weekly Weather Forecast for Chicago

How to Book Your Chicago 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 Chicago

More Top-Rated Vacation Rentals in Chicago 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 outdoor seating areas such as patios or balconies for relaxing in the fresh air.
  • Take advantage of shared or private gardens where you can unwind amidst greenery.
  • Make the most of nearby parks and green spaces perfect for outdoor activities and picnics.
  • Look for rentals with outdoor grills or barbecue facilities to host cookouts during your stay.
  • Some properties may offer outdoor pools or hot tubs for a refreshing dip on warm days.
  • Explore outdoor recreational amenities like tennis courts or sports courts available nearby or on-site.
  • Check for convenient access to walking or biking trails that showcase the area's scenic views.

Top Attractions Around Chicago

What attractions are nearby?

In the vibrant area surrounding your vacation rental, you can enjoy a variety of activities including exploring world-class museums, strolling through scenic parks, and experiencing the lively local dining scene that make this destination truly unforgettable.

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Family Activities

  • Shedd Aquarium: Discover the wonders of marine life at this popular Chicago attraction, perfect for family exploration in the area.
  • Millennium Park: Enjoy outdoor art installations, wide-open spaces, and iconic sights like Cloud Gate, making it a great spot for family picnics and activities in the city center.
  • Lincoln Park Zoo: Visit one of the oldest free zoos in the country, offering engaging exhibits and animal encounters for all ages within the region.
  • Field Museum of Natural History: Immerse your family in fascinating exhibits about natural history and culture that are both educational and entertaining here in Chicago.
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Adult Activities

  • Visit Millennium Park: Explore this iconic urban space featuring stunning public art, including the famous Cloud Gate sculpture, perfect for leisurely strolls and photo opportunities in the heart of downtown.
  • Experience the Art Institute of Chicago: Immerse yourself in world-renowned artworks and exhibitions at this cultural hub, just a short distance from your comfortable vacation rentals here.
  • Take an Architectural River Cruise: Discover the stunning skyline and architectural history of the city on a guided boat tour along the Chicago River, offering breathtaking views from unique perspectives.
  • Dine in the Fulton Market District: Indulge in diverse culinary experiences at trendy restaurants within this vibrant neighborhood, making it an ideal spot for food enthusiasts staying in nearby vacation rentals.

Other Places to Stay in Chicago, IL

Cook County
Cook County Vacation Rentals
Chicago
Chicago Vacation Rentals
Central Chicago
Central Chicago Vacation Rentals
Downtown Chicago
Downtown Chicago Vacation Rentals
Near North Side
Near North Side Vacation Rentals
The Loop
The Loop Vacation Rentals
West Side
West Side Vacation Rentals
North Side
North Side Vacation Rentals
Lake County
Lake County Vacation Rentals
DuPage County
DuPage County Vacation Rentals
River North
River North Vacation Rentals
South Side
South Side Vacation Rentals
More Places to Stay Near Chicago

Chicago Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Neighborhoods: Discover the diverse neighborhoods in the area to experience authentic local culture and find hidden gems close to your vacation rentals.
  • Plan Your Transportation: Utilize the region’s public transit options or consider renting a bike to conveniently explore popular attractions from your Chicago accommodation.
  • Visit Iconic Landmarks: Make time for must-see landmarks nearby to get a true sense of the city’s history and architecture during your stay.
  • Sample Regional Cuisine: Indulge in the area's renowned culinary scene by visiting local eateries near your rental for an authentic taste experience.

Transportation Options

  • CTA Bus Service: This affordable and extensive bus network efficiently connects you to key neighborhoods and attractions throughout the area, making public transit a convenient choice for exploring.
  • CTA 'L' Trains: The elevated train system offers quick and reliable transportation across the region, ideal for navigating here without the hassle of parking or traffic.
  • Divvy Bike Sharing System: With numerous stations around the area, renting a bike provides an eco-friendly and flexible way to discover local sights at your own pace.
  • Rideshare Options: Popular services like Uber and Lyft operate extensively here, offering a comfortable and hassle-free way to get around, especially during busy times.

Local Customs Options

  • Chicago-style Deep Dish Pizza: You should definitely try the iconic deep-dish pizza here, which is a culinary tradition that locals take pride in sharing with visitors.
  • Blues Music Roots: Embrace the soulful sounds of blues, a vital part of the area's musical heritage, often celebrated in local venues and festivals.
  • Street Art and Murals: Explore the vibrant street art scene that boasts colorful murals reflecting the city's diverse culture and history.
  • Festive Parades and Events: Participate in lively parades such as the annual St. Patrick’s Day parade, which showcases the region's community spirit and local traditions.

Frequently Asked Questions About Chicago?

1. What are the top vacation rentals in Chicago?

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

2. How many vacation rentals have private pools in Chicago?

There are 319 vacation rentals with private pools near Chicago. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chicago are best for families?

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

4. How many Rentbyowner vacation rentals are available in Chicago?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 10426 in the Chicago 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 Chicago. 

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

Cancellation policies vary by property, so it’s important to review the specific listing details when booking here. Policies may include free cancellations within a certain period or restrictions on refunds, depending on the owner’s preferences.

6. How do I contact the property owner or manager before booking my stay?

You can reach out directly to the owner or property manager through the messaging system provided on the listing page. This allows you to ask questions about the rental, amenities, or any specific needs related to your visit.

7. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the property's listing. Be sure to review these details carefully before confirming your reservation to understand the total cost.

8. What amenities should I look for in vacation rentals here to ensure a comfortable stay?

Look for key amenities such as Wi-Fi, air conditioning, kitchen facilities, and secure parking. These features help enhance your comfort and convenience during your visit to the region.

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

Minimum stay requirements can differ between properties, especially during peak seasons or special events. Check each listing’s policy to confirm the duration needed for your stay before making a reservation.