Discover Your Perfect Near North Side Vacation Homes

Best Vacation Homes in Near North Side

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Near North Side Luxury Rentals

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Find More Near North Side Villas, Resorts, & Rentals on BedroomVillas

Near North Side Pet Friendly Vacation Rentals

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9.6 (166 Reviews)
Apartment
Kasa River North Chicago
  • Air Conditioner
  • Pet Friendly
  • Pool
View Availability
See More Pet-Friendly Vacation Rentals in Near North Side on PetFriendly.io

Why Choose Rent By Owner for your Near North Side 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 Near North Side Vacation Rentals

Where are the best neighborhoods to stay in Near North Side?

When choosing where to stay near North Side in Chicago, Illinois, you'll find a vibrant neighborhood that offers easy access to the city's iconic attractions and lively urban scene. This area is known for its mix of modern convenience and classic Chicago charm, making it an excellent base for exploring everything the city has to offer. Whether you're looking for stylish apartments or cozy homes, there are plenty of vacation rentals that provide comfort and reliability right in the heart of Near North Side. Booking through trusted vacation rental platforms ensures a seamless experience, so you can focus on enjoying your trip to this dynamic part of Chicago.

Downtown Chicago

Stay in the heart of the city’s vibrant core, where your accommodation offers easy access to iconic landmarks and a lively urban atmosphere. This area provides a perfect base for exploring Chicago’s cultural attractions and bustling streets.

View 1753+ Rentals in Downtown Chicago

Magnificent Mile

Enjoy the luxury and shopping opportunities along this famous corridor, placing you close to high-end boutiques and exquisite dining options. Staying here ensures convenience and excitement right outside your door.

View 4128+ Rentals in Magnificent Mile

The Loop

Situated at the financial and cultural center of the city, accommodations here offer proximity to renowned theaters, museums, and historic architecture. It's an ideal choice for those wanting to immerse themselves in Chicago’s dynamic arts scene.

View 775+ Rentals in The Loop

River North

Known for its vibrant nightlife, art galleries, and trendy restaurants, River North is perfect for travelers seeking an energetic and stylish neighborhood. Your stay here puts you in close proximity to some of the region’s most fashionable venues.

View 450+ Rentals in River North

Lincoln Park

Relax in this lush, park-filled neighborhood that offers a peaceful retreat from the city buzz, while still being near the region’s major attractions. It’s an ideal destination for outdoor enthusiasts and families alike.

View 143+ Rentals in Lincoln Park

West Loop

Experience the culinary renaissance of this trendy area, known for its innovative restaurants and vibrant food scene. Staying in this part of town grants you convenient access to both entertainment and excellent dining experiences.

View 197+ Rentals in West Loop

Gold Coast

This upscale neighborhood features elegant architecture and boutique shopping, offering a luxurious environment for your stay. It’s an excellent choice for those looking to combine comfort with style.

View 39+ Rentals in Gold Coast

Old Town

Step into a neighborhood rich with history and charm, known for its lively community and eclectic shops. Here, your accommodation provides a cozy yet accessible base for exploring local culture.

View 53+ Rentals in Old Town

Best Times to Visit Near North Side

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination can greatly enhance your experience, allowing you to enjoy the vibrant atmosphere and nearby attractions in the region while making the most of your vacation rental here.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this area experiences warm weather and vibrant city events, making it ideal for exploring outdoor attractions and cultural festivals.

Average Temperature Daytime: 80-88°F - Nighttime: 65-70°F
autumn
Fall (September to November)

Autumn brings cooler temperatures and beautiful fall foliage, providing a perfect setting for sightseeing and enjoying the local arts scene.

Average Temperature Daytime: 65-75°F - Nighttime: 50-58°F

Off-Season Highlights

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Winter (December to February)

The winter season offers fewer crowds and some indoor events, with colder weather that is great for cozy stays in your vacation rentals.

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

As nature begins to bloom, you can experience milder weather and fewer tourists, making it an excellent time for sightseeing and exploring the area's cultural offerings.

Average Temperature Daytime: 55-70°F - Nighttime: 40-50°F

Weekly Weather Forecast for Near North Side

How to Book Your Near North Side 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 Near North Side

More Top-Rated Vacation Rentals in Near North Side 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

  • Access to a private or shared outdoor terrace, balcony, or patio to enjoy the city views
  • Outdoor seating areas equipped with tables and chairs for dining al fresco or relaxing outdoors
  • Shared or private rooftop deck offering panoramic vistas of the skyline
  • On-site garden or landscaped courtyard to unwind amidst greenery
  • Fitness facilities including outdoor exercise equipment or running tracks nearby
  • Nearby parks or green spaces perfect for outdoor activities and leisurely strolls
  • Secure bicycle storage or bike-sharing stations for exploring here on two wheels

Top Attractions Around Near North Side

What attractions are nearby?

In this vibrant area, you can enjoy a variety of activities such as exploring world-class shopping, dining at renowned restaurants, or taking in the stunning skyline views—all conveniently located near your vacation rental in Near North Side, Chicago.

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Family Activities

  • Millennium Park: Enjoy family-friendly outdoor activities and stunning public art installations in this iconic park close to your vacation rental.
  • Shedd Aquarium: Explore a diverse array of marine life exhibits, offering an educational and entertaining experience for children and adults alike.
  • The Art Institute of Chicago: Introduce the family to world-renowned art collections, providing engaging exhibits suitable for all ages within walking distance of your stay.
  • Lake Michigan Beaches: Relax and have fun building sandcastles or splashing in the water at nearby beaches along the scenic Lake Michigan shoreline.
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Adult Activities

  • Visit the Art Institute of Chicago: Immerse yourself in world-class art collections right in the heart of the city, offering a culturally enriching experience during your stay.
  • Explore Navy Pier: Enjoy scenic views, dining options, and entertainment at this iconic waterfront destination that is perfect for leisurely adult outings.
  • Experience the Magnificent Mile: Shop at luxury retailers and historic boutiques along this famous stretch, ideal for those seeking upscale retail therapy.
  • Enjoy fine dining and nightlife: Discover a variety of restaurants and bars in the area that cater to sophisticated tastes and provide vibrant evening entertainment.

Other Places to Stay in Near North Side, IL

Goose Island
Goose Island Vacation Rentals
Legacy Motors Automotive Art Gallery
Legacy Motors Automotive Art Gallery Vacation Rentals
Pump It Up Party Zone
Pump It Up Party Zone Vacation Rentals
Cooking & Hospitality Institute of Chicago
Cooking & Hospitality Institute of Chicago Vacation Rentals
Judy A Saslow Gallery
Judy A Saslow Gallery Vacation Rentals
Michigan Avenue
Michigan Avenue Vacation Rentals
Magnificent Mile
Magnificent Mile Vacation Rentals
River North
River North Vacation Rentals
Streeterville
Streeterville Vacation Rentals
Rush and Division
Rush and Division Vacation Rentals
Gold Coast
Gold Coast Vacation Rentals
Killgubbin
Killgubbin Vacation Rentals
More Places to Stay Near Near North Side

Near North Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Neighborhood: Take time to walk around and discover the vibrant local scene, ensuring you experience the area's best dining, shops, and cultural spots during your stay.
  • Plan Your Transit: Utilize the region’s public transportation options or walkable streets to easily access the main attractions without the hassle of parking or traffic.
  • Book Centrally Located Vacation Rentals: Choose accommodations close to popular destinations to maximize your time and enjoy the convenience of nearby amenities.
  • Check for Local Events: Stay updated on events and festivals happening during your visit to immerse yourself in the community's lively atmosphere.

Transportation Options

  • Chicago Transit Authority (CTA) Rail and Bus:** This region is well-connected by the CTA, offering convenient train and bus options to explore the city efficiently from your vacation rental.
  • Divvy Bike Shares: For an active way to see the area, bike-sharing stations provide easy access to bicycles, allowing you to enjoy the neighborhood at your own pace.
  • Taxi and Rideshare Services: Trusted services like Uber and Lyft operate extensively here, providing reliable transportation for quick trips or late-night returns to your rental.
  • Rental Car Services: If independence is a priority, numerous car rental agencies are available nearby, giving you the flexibility to explore beyond the immediate vicinity of your vacation rental.

Local Customs Options

  • Jazz Music Culture: Embrace the area's vibrant jazz scene by visiting local clubs and understanding its significance to the region's musical heritage.
  • Architectural Appreciation: Appreciate the modern and historic architecture that defines this destination, reflecting its innovative spirit and rich history.
  • Lake Michigan Traditions: Observe the customs and activities centered around Lake Michigan, which plays a vital role in the lifestyle here.
  • Food and Dining Etiquette: Experience the culinary culture through local dining traditions that highlight the area's diverse cuisine options.

Frequently Asked Questions About Near North Side?

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:

2. How many vacation rentals have private pools in Near North Side?

There are 27 vacation rentals with private pools near Near North Side. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Near North Side are best for families?

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

4. 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 1132 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. 

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

Cancellation policies vary by listing; you should review the specific property's cancellation terms on the booking page or contact the owner directly to understand the options and any associated fees.

6. How do I ensure my reservation is secure when booking here?

Reservations are secured through a trusted platform that offers secure payment options. Always confirm your booking details directly with the property owner and look for verified listings to ensure safety.

7. Are there any house rules or restrictions I should know before booking?

Yes, each vacation rental will have its own house rules and restrictions. These are typically detailed in the listing description, so be sure to read them carefully or reach out to the host for clarification.

8. What amenities are typically included in vacation rentals in this neighborhood?

Most properties offer amenities such as Wi-Fi, kitchen facilities, and laundry services. For a complete list of what's available, check the specific listing details or contact the owner directly.

9. How do I find the best vacation rental in this region for my stay?

To find the ideal property, filter your search based on your preferences like location, amenities, and budget. Reading reviews and contacting the owner can also help ensure the rental meets your expectations.