Chicago Rentals by Owner
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Why Choose Rent By Owner for your Chicago vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Chicago Rentals by Owner
Where are the best neighborhoods to stay in Chicago?
When planning your stay in Chicago, Illinois, choosing the right neighborhood can significantly enhance your experience. Whether you're looking to explore vibrant city life, enjoy cultural attractions, or relax in a quieter setting, each area offers unique charm and convenience. Chicago's neighborhoods provide a diverse range of rental options, making it easy to find a rental by owner that suits your preferences. With trusted vacation rentals available through Rent By Owner, you can discover the perfect place to stay within this dynamic city, ensuring a seamless and enjoyable visit to the Windy City.
Downtown Chicago
Staying in this central area places you close to Chicago's vibrant city life and iconic skyline, offering convenient access to a variety of local amenities and entertainment options. It's an ideal choice for those seeking a lively atmosphere combined with easy access to transportation and business districts.
View 1739+ Rentals in Downtown ChicagoMagnificent Mile
This renowned shopping and cultural district provides a prime location for exploring upscale retail, fine dining, and stunning architecture. Choosing accommodations here ensures you're at the heart of the region's most stylish and energetic neighborhood.
View 4128+ Rentals in Magnificent MileThe Loop
The bustling core of the city's downtown, this neighborhood is perfect for immersing yourself in Chicago’s arts, theater, and business scenes, all within walking distance of major attractions and transit hubs that make exploring effortless.
View 755+ Rentals in The LoopRiver North
Known for its vibrant art galleries, trendy restaurants, and nightlife, this district offers an exciting stay for visitors looking to experience Chicago's creative spirit and urban energy while remaining centrally located.
View 445+ Rentals in River NorthHyde Park
This historic neighborhood blends academic excellence with cultural diversity, providing a peaceful yet stimulating environment that is perfect for visitors interested in exploring Chicago’s rich intellectual and artistic history.
View 120+ Rentals in Hyde ParkLincoln Park
Set against the scenic backdrop of a large public park, this neighborhood offers a relaxed atmosphere with easy access to outdoor activities, local museums, and charming shops, making it an excellent choice for those seeking a more laid-back stay.
View 161+ Rentals in Lincoln ParkO'Hare
Conveniently situated near one of the world’s busiest airports, this area is ideal if proximity to travel hubs is your priority, providing quick transit options and comfortable accommodations for jet-setting visitors.
View 65+ Rentals in O'HareLakeview
A lively neighborhood known for its diverse entertainment options and vibrant community, here you will find plenty of local eateries, music venues, and sports venues, perfect for experiencing Chicago’s dynamic urban culture.
View 267+ Rentals in LakeviewBest Times to Visit Chicago
When should you plan your Rentals by Owner stay?
Understanding the optimal times to visit ensures you can enjoy all that this vibrant city has to offer while making the most of your rental by owner experience here.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you will experience lively events and a bustling atmosphere in the region, making it ideal for exploring local attractions.
Fall (September to November)
Autumn offers mild weather and vibrant foliage, perfect for enjoying outdoor activities and taking advantage of the area's cultural festivals.
Off-Season Highlights
Winter (December to February)
The winter season brings colder temperatures and fewer tourists, providing a more relaxed atmosphere for exploring the city's indoor attractions.
Early Spring (March to April)
As the region transitions out of winter, you can enjoy fewer crowds and lower rates while experiencing the early signs of spring's arrival.
Weekly Weather Forecast for Chicago
How to Book Your Chicago vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chicago
Common Rentals by Owner Amenities
What amenities can you expect?
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 seating areas such as patios or balconies perfect for relaxing or dining al fresco.
- Take advantage of landscaped gardens or green spaces that provide a peaceful retreat right at your rental.
- Make use of private or shared courtyards ideal for socializing or unwinding in the fresh air.
- Benefit from access to nearby parks or walking trails to explore the region’s natural beauty.
- Utilize outdoor recreational amenities like grills, picnic areas, or fire pits available on the property.
- Experience scenic views through large windows or outdoor terraces that showcase the vibrant surroundings.
- Stay fit and active with outdoor fitness equipment or designated sports courts often found in the area.
Top Attractions Around Chicago
What attractions are nearby?
Within the vibrant region, you can explore a variety of activities, from cultural attractions to outdoor adventures, all conveniently close to your rental by owner in Chicago, Illinois, ensuring an engaging and memorable stay.
Family Activities
- Shedd Aquarium: Discover fascinating marine life exhibits that captivate children and adults alike, making it a must-visit in the area.
- Museum of Science and Industry: Engage with interactive displays and hands-on activities that make learning fun for the entire family here.
- : Enjoy free admission at this historic zoo, where a diverse array of animals provides entertainment for all ages within scenic surroundings.
- : Experience family-friendly attractions, rides, and entertainment along the iconic waterfront, perfect for creating lasting memories.
Adult Activities
- Visit Millennium Park: Enjoy outdoor art installations and live performances in the iconic space right in the heart of the city, perfect for experiencing local culture.
- Explore Navy Pier: Discover a variety of entertainment options, including rides, restaurants, and stunning views of the lake, all within a short distance from your rental.
- Tour the Art Institute of Chicago: Immerse yourself in world-renowned artworks and innovative exhibits housed in one of the region's top cultural institutions.
- Experience the Architecture River Cruise: See the area's celebrated skyline from the water while learning about its historic and modern architectural marvels, an ideal activity for those staying nearby.
Other Places to Stay in Chicago, IL
Chicago Travel Tips
How Can You Make the Most of Your Stay?
- Explore local neighborhoods: Take time to discover the distinct neighborhoods that make this destination unique, offering authentic experiences and convenient access to your rental by owner accommodations.
- Plan your transportation in advance: Utilize public transit options or arrange reliable car rentals to navigate efficiently through this region's popular sights and hidden gems.
- Make the most of cultural events: Check the local event calendar to attend festivals, markets, or performances that showcase the area's vibrant arts scene during your stay.
- Prioritize safety and comfort: Select a well-reviewed rental by owner that provides essential amenities, ensuring a secure and enjoyable experience throughout your visit here.
Transportation Options
- Chicago Transit Authority (CTA) trains: This fast and reliable subway system connects key neighborhoods, making it easy for you to explore the area efficiently.
- Metra commuter trains: Designed for longer trips across the region, they offer convenient connections from your rental to suburban destinations.
- Bus services: Extensive bus networks provide flexible transportation options within the region, ideal for reaching places not accessible by train.
- Taxis and ride-sharing services: Easily hailed or booked via apps, offering door-to-door convenience throughout the city and surrounding areas.
Local Customs Options
- Greeting Etiquette: When visiting here, it’s customary to greet locals with a friendly smile and a handshake, reflecting the region’s welcoming spirit.
- Dining Customs: Sharing meals family-style is common, and tipping around 15-20% at local eateries shows appreciation for service in this area.
- Public Behavior: Maintaining a polite and respectful demeanor is appreciated, especially during festivals and community events typical of this destination.
- Sports Loyalty: Showing enthusiasm for local sports teams can be a great way to connect with residents and embrace the regional culture.
Frequently Asked Questions About Chicago Rentals by Owner
What are the top rated 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:
- 52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55-56 Mag Mile Penthouse
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- Magic Factory Loft 2West
- 51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
Which is the best family rental in Chicago?
Can we get self-catering vacation rentals in Chicago?
What are the best luxury vacation rentals near Chicago?
Can we bring our dog to our vacation rental in Chicago?
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