Near North Side Rentals by Owner
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- View
- Balcony/Terrace
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Security/Safety
Why Choose Rent By Owner for your Near North Side vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Near North Side Rentals by Owner
Where are the best neighborhoods to stay in Near North Side?
When exploring places to stay near North Side in Chicago, Illinois, you’ll find a vibrant neighborhood offering a variety of rental options perfect for different travel preferences. Staying in this area provides convenient access to the city’s dynamic attractions while enjoying the comfort and privacy of a rental by owner. Whether you're seeking a lively atmosphere or a more relaxed environment, choosing accommodations in this sought-after part of Chicago ensures a memorable stay. Trust Rent By Owner for a seamless booking experience, connecting you with dependable vacation rentals in Near North Side that meet your specific needs.
Downtown Chicago
Staying in the heart of the city offers easy access to iconic landmarks and vibrant urban adventures, making it an ideal choice for travelers seeking convenience and city excitement.
View 1791+ Rentals in Downtown ChicagoMagnificent Mile
Known for its upscale shopping and stunning skyline views, this area provides a sophisticated backdrop for your stay while remaining close to top attractions and dining options.
View 4128+ Rentals in Magnificent MileThe Loop
This central neighborhood is perfect for exploring Chicago’s cultural scene, with a variety of theaters, museums, and business hubs within walking distance.
View 775+ Rentals in The LoopRiver North
Renowned for its vibrant arts district and lively nightlife, here you can enjoy an energetic atmosphere combined with easy access to downtown sights.
View 484+ Rentals in River NorthLincoln Park
A picturesque neighborhood offering lush green spaces and historic architecture, ideal for those who want a quieter retreat with proximity to city attractions.
View 143+ Rentals in Lincoln ParkWest Loop
Famous for its innovative culinary scene and trendy boutiques, this region blends modern charm with convenient access to downtown conveniences.
View 198+ Rentals in West LoopGold Coast
Elegant streets and luxury accommodations define this upscale neighborhood, providing a refined base for experiencing Chicago’s high-end lifestyle.
View 39+ Rentals in Gold CoastOld Town
With its historic charm and eclectic vibe, this neighborhood offers a cozy yet lively environment close to the city’s main attractions.
View 53+ Rentals in Old TownBest Times to Visit Near North Side
When should you plan your Rentals by Owner stay?
Choosing the right time to visit here can enhance your experience, as the area's vibrant seasons offer various opportunities to enjoy its unique attractions and local events throughout the year.
Peak Season Highlights
Summer (June to August)
During the summer months, this area experiences its peak tourist season, with warm weather attracting visitors who want to enjoy outdoor activities and city events.
Fall (September to November)
Early fall is also a bustling time here, as visitors come to experience the vibrant city atmosphere and colorful foliage in the nearby parks.
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors here, offering a quieter stay when you can enjoy the city’s indoor attractions and holiday cheer.
Early Spring (March to April)
In early spring, the region experiences a slowdown in tourism, making it an ideal time for those seeking more peaceful accommodations by owner.
Weekly Weather Forecast for Near North Side
How to Book Your Near North Side vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Near North Side
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 access to a private outdoor patio or balcony, perfect for relaxing and taking in the city views.
- Take advantage of on-site outdoor grilling areas for preparing meals during your stay.
- Make use of the communal rooftop terrace, offering panoramic sights of the skyline and Lake Michigan.
- Benefit from nearby parks and green spaces for jogging, picnicking, or outdoor recreation.
- Utilize secure bike storage if you prefer exploring the area by bicycle.
- Access outdoor swimming pools that provide a refreshing retreat during warmer months.
- Enjoy well-maintained walkways and outdoor seating areas designed for socializing and leisure.
Top Attractions Around Near North Side
What attractions are nearby?
In this vibrant neighborhood, you can enjoy a variety of nearby activities, including exploring cultural attractions, shopping districts, and dining options, all easily accessible from your rental by owner stay in the area.
Family Activities
- Lincoln Park Zoo: Enjoy a day exploring one of the oldest free zoos in the country, perfect for family fun and wildlife education.
- Magnificent Mile Shopping and Sightseeing: Stroll through this iconic stretch to experience shops, landmarks, and engaging street performances suitable for all ages.
- Chicago Children's Museum: Discover interactive exhibits and hands-on activities designed to inspire and entertain young visitors within the nearby Navy Pier area.
- Navy Pier Ferris Wheel: Take a ride on the historic Ferris wheel for breathtaking views of the city skyline and Lake Michigan—an essential family activity during your stay here.
Adult Activities
- Sightseeing and Architectural Tours: Discover the iconic skyline and historic buildings during guided tours that delve into the area's architectural heritage.
- Visit to Art Galleries and Museums: Explore renowned art institutions showcasing contemporary and classic works, perfect for cultural engagement in this vibrant region.
- Dining Experiences at Upscale Restaurants: Indulge in a variety of culinary delights at high-end eateries that reflect the diverse food scene here.
- Nightlife and Entertainment Venues: Enjoy lively bars, theaters, and music venues that offer entertainment options after sunset in this dynamic part of the city.
Other Places to Stay in Near North Side, IL
Near North Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the region’s renowned culinary scene by trying nearby restaurants and cafes to experience authentic flavors.
- Plan your transportation: Use public transit or walk through this vibrant area to maximize convenience and immerse yourself in the local atmosphere.
- Visit popular attractions early: Arrive at key spots during off-peak hours to enjoy a more relaxed experience and make the most of your time here.
- Book your stay with trusted hosts: Choose rentals by owner in the area for personalized service and a comfortable, home-like atmosphere during your visit.
Transportation Options
- Chicago Transit Authority (CTA) Trains: The CTA train system provides quick and reliable transportation throughout the city, making it easy to explore the nearby attractions from your rental.
- Bus Services: Extensive bus routes connect various neighborhoods within this vibrant area, offering an affordable and convenient way to get around without a car.
- Divvy Bicycle Sharing: For a flexible and eco-friendly option, the bike-sharing program allows you to navigate the region at your own pace while enjoying the city views.
- Taxi and Rideshare Services: Taxis and rideshare options such as Uber and Lyft are readily available here, providing comfort and convenience for longer trips or late-night outings.
Local Customs Options
- Respect for Local Dining Etiquette: You’ll notice that dining customs here emphasize politeness and shared communal experiences, reflecting the area's vibrant culinary culture.
- Celebration of Cultural Festivals: Participating in or observing local festivals and events allows you to enjoy this region's rich traditions and community spirit.
- Appreciation for Architectural Styles: The area’s distinctive architecture is appreciated through respectful observation and careful interaction with historic sites and buildings.
- Emphasis on Arts and Music Appreciation: Engaging with local arts scenes and music performances offers a deeper connection to this destination's creative heritage.
Frequently Asked Questions About Near North Side Rentals by Owner
1. What are the top vacation rentals in Near North Side?
There are a lot of options in Near North Side. If you plan on staying in the Near North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Near North Side:
- Magic Factory Loft 2West
- Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
- City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
- Luxury Loft Collection 02 - Terrace - River North
- Luxury Loft Collection 703 - Terrace - River North
- Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
- 53-54 Floor Penthouse
- Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
2. How many Rentbyowner vacation rentals are available in Near North Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 852 in the Near North Side 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 Near North Side.
3. What is the cancellation policy for rental by owner accommodations in this area?
4. How do I communicate with the property owner during my stay?
5. Are there any house rules I should be aware of when staying here?
6. Is the property equipped with amenities like Wi-Fi and parking?
7. What steps should I take if I encounter an issue during my stay?
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