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Discover Your Perfect Chicago Rentals by Owner

Chicago Rentals by Owner

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10.0 (21 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
View Availability
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10.0 (12 Reviews)
Apartment
Uptown Gem
  • Air Conditioner
  • Parking
  • Pool
View Availability
More Top-Rated Rentals by Owner in Chicago Area

Why Choose Rent By Owner for your Chicago vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner

Where are the best neighborhoods to stay in Chicago?

When planning your stay in Chicago, Illinois, exploring the neighborhoods to stay in can greatly enhance your experience. Each area offers its own unique charm and convenient access to key attractions, making it easier to enjoy the city like a local. Whether you prefer the vibrant energy of downtown Chicago or the historic character of neighborhoods further afield, finding the right rental by owner through Rent By Owner ensures a trustworthy and seamless booking process. By selecting an area that suits your interests, you'll have a more authentic and comfortable visit to this dynamic city in Illinois.

Downtown Chicago

Staying in the heart of the city offers immediate access to the area's vibrant business district and cultural landmarks, making it an ideal choice for travelers seeking convenience and excitement. Here, you'll find your rental by owner close to premier shopping, dining, and entertainment options.

View 2288+ Rentals in Downtown Chicago

Magnificent Mile

This bustling neighborhood is perfect if you want to immerse yourself in high-end retail, luxury accommodations, and stunning city views. The area ensures a memorable stay with easy access to some of the most iconic shopping streets nearby.

View 4128+ Rentals in Magnificent Mile

The Loop

Situated in the city's central business district, the region is ideal for exploring Chicago's financial core and cultural institutions, all within walking distance. Your rental here allows convenient access to theaters, museums, and distinctive architecture.

View 1324+ Rentals in The Loop

River North

Known for its vibrant arts scene and lively nightlife, this neighborhood is great for visitors wanting an energetic atmosphere combined with stylish dining and boutique shops. Staying here places you close to some of the area's most popular entertainment venues.

View 384+ Rentals in River North

Hyde Park

This historic neighborhood provides a peaceful and scholarly ambiance, perfect for those interested in cultural attractions and educational institutions. It’s an excellent choice for a more relaxed yet enriching experience during your visit.

View 110+ Rentals in Hyde Park

Lincoln Park

Offering a blend of lush green spaces and trendy neighborhoods, this area is suitable for travelers seeking outdoor activities along with vibrant dining options. Your rental here puts you close to scenic parks and lively streets.

View 186+ Rentals in Lincoln Park

O'Hare

Ideal for travelers prioritizing proximity to the airport, this area provides convenient access for easy arrivals and departures. It’s a practical choice for those who prefer quick transfers without sacrificing comfort.

View 76+ Rentals in O'Hare

Lakeview

This lively neighborhood is perfect for visitors looking for a mix of entertainment, local bars, and diverse dining experiences, all within a friendly community setting. Staying here offers easy access to lakeside parks and vibrant nightlife.

View 319+ Rentals in Lakeview

Best Times to Visit Chicago

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here can enhance your experience, allowing you to enjoy the region's unique atmosphere while making the most of your rental by owner in Chicago.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather ideal for outdoor exploration and events, making it a lively time to visit.

Average Temperature Daytime: Approximately 85°F (29°C) - Nighttime: Around 70°F (21°C)
autumn
Fall (September to November)

The fall season offers vibrant foliage and mild temperatures, creating a scenic backdrop that enhances your stay in this destination.

Average Temperature Daytime: Roughly 70°F (21°C) - Nighttime: Approximately 55°F (13°C)

Off-Season Highlights

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Winter (December to February)

In winter, the region cools down substantially, offering a quieter experience for those seeking fewer crowds and cozy accommodations.

Average Temperature Daytime: Around 35°F (1.5°C) - Nighttime: Close to 20°F (-6°C)
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Early Spring (March to April)

As the area transitions into spring, temperatures remain relatively cool, providing a peaceful escape before the busy tourist season begins.

Average Temperature Daytime: Approximately 50°F (10°C) - Nighttime: About 35°F (2°C)

Weekly Weather Forecast for Chicago

How to Book Your Chicago vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Chicago Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

  • You can enjoy access to outdoor seating areas, perfect for relaxing or dining al fresco in the region.
  • Many rentals offer private patios or decks where you can unwind while taking in the surrounding city views.
  • Look for properties with shared or private gardens that provide a peaceful outdoor retreat within the area.
  • Some listings feature outdoor grills or barbecue setups, ideal for hosting gatherings here in the region.
  • Experience the convenience of designated parking spaces often available alongside outdoor amenities in this destination.
  • Neighborhoods frequently include access to nearby parks or green spaces, perfect for outdoor activities.
  • Outdoor recreational facilities such as pools or sports courts are common features in select vacation rentals in this region.

Top Attractions Around Chicago

What attractions are nearby?

While staying in this vibrant destination, you can enjoy a variety of nearby activities such as exploring cultural landmarks, indulging in exceptional dining experiences, and experiencing the lively arts scene that truly captures the essence of the region.

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Family Activities

  • Lincoln Park Zoo: Enjoy a free and family-friendly visit to this renowned zoo, where you can see a variety of animals in naturalistic habitats within the city’s scenic park setting.
  • Museum of Science and Industry: Explore interactive exhibits and hands-on activities that make learning fun for children and adults alike at this top science museum in the region.
  • Shedd Aquarium: Discover marine life through engaging displays and exciting animal encounters at this beloved aquarium located along the lakefront.
  • Millennium Park: Experience outdoor art installations, open green spaces, and family-friendly events in this iconic destination situated downtown.
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Adult Activities

  • Visit Millennium Park: Experience the region's vibrant arts and culture scene while exploring iconic landmarks like the Cloud Gate sculpture in this downtown Chicago destination.
  • Enjoy a river architecture cruise: Discover the impressive skyline and innovative design of this area through an engaging boat tour that showcases the city’s renowned architectural heritage.
  • Explore the Art Institute of Chicago: Immerse yourself in world-class art collections at this cultural hub, conveniently located near many rental accommodations in the city.
  • Dine along the Chicago Riverwalk: Savor diverse culinary offerings and scenic views as you stroll this popular waterfront promenade in the region.

Other Places to Stay in Chicago, IL

Chicago
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The Loop
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Near North Side
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North Side
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Far North Side
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South Side
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South Loop
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River North
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Near South Side
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More Places to Stay Near Chicago

Chicago Travel Tips

How Can You Make the Most of Your Stay?

  • Explore iconic neighborhoods: Take the time to stroll through local districts to experience authentic vibes and discover hidden gems that truly define the area's unique character.
  • Utilize transportation options efficiently: Leverage public transit or ride-share services to navigate easily, saving time and enjoying affordable travel within the city.
  • Plan ahead for popular attractions: Book tickets in advance for must-see spots to avoid long lines and guarantee your access during peak times.
  • Choose a rental in a central location: Opt for accommodations near key transport hubs and vibrant neighborhoods to maximize your sightseeing opportunities with ease.

Transportation Options

  • CTA Bus System: The area is well-served by the Chicago Transit Authority, offering extensive bus routes that make exploring the city and beyond convenient for visitors staying in rental accommodations here.
  • Chicago 'L' Train Network: This rapid transit system provides quick access to key neighborhoods and attractions, making it an efficient way for you to navigate your stay in this vibrant region.
  • Divvy Bike Share: For an eco-friendly and flexible transportation option, the bike-sharing program allows you to explore the city’s scenic spots at your own pace without leaving the neighborhood.
  • Taxi and Rideshare Services: Reliable taxi cabs and rideshare options like Uber and Lyft are readily available, providing direct and comfortable travel throughout the area.

Local Customs Options

  • Greeting and Personal Space: When visiting locals, you’ll notice that informal greetings like a handshake or a friendly nod are common in the area.
  • Food Etiquette: Sharing a meal often involves casual dining with an emphasis on hearty, traditional dishes that reflect the region’s culinary heritage.
  • Respect for Architecture: Appreciating the historic architecture and skyline is a key part of the local customs, so be mindful when exploring urban neighborhoods here.
  • Attire and Dress Code: In this destination, dressing comfortably yet stylishly is appreciated, especially when attending cultural events or dining out in popular districts.

Chicago Rentals by Owner Frequently Asked Questions

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 Rentbyowner vacation rentals are available in Chicago?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 5607 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. 

3. How can I find detailed information about the cancellation policy for a rental by owner in Chicago?

You should review the specific listing details on the Rent By Owner platform, as cancellation policies vary by property. For further clarification, contact the property owner directly before finalizing your booking.

4. What should I know about checking in and check-out times when renting directly from an owner here?

Check the individual listing for the designated check-in and check-out procedures, as these can differ between properties. Confirm these times with the owner to ensure a smooth arrival and departure.

5. Are there any specific rules or requirements I need to be aware of when booking an owner-operated rental in this area?

Yes, each property may have its own set of house rules and requirements. These are usually outlined in the listing description; if not, reach out to the owner for details to ensure compliance during your stay.

6. How do I handle potential issues or emergencies during my stay at a rental by owner in this destination?

Contact the property owner immediately through the communication channels provided on the platform. It's advisable to clarify emergency procedures and contact information prior to your arrival.

7. What steps should I take to confirm the reservation and secure my stay in this region?

Complete all required booking steps on the Rent By Owner website, including payment verification and communication with the owner. Reading the listing carefully and asking questions beforehand helps ensure your reservation is confirmed smoothly.

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More Top-Rated Rentals by Owner in Chicago Area