Near North Side vacation rentals

We found 1,146 vacation rentals — enter your dates for availability

Discover a selection of 499 apartments, 28 condos, and other vacation rentals in Near North Side that are perfect for your trip. Vacation rentals provide the best amenities for your family, friends, or furry companion, like air conditioning and WiFi. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.

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Find out more about Near North Side

Why visit Near North Side

  • Iconic Skyscrapers: Marvel at the stunning architecture of Chicago's famous skyscrapers that define the city skyline.
  • Vibrant Riverfront: Enjoy leisurely strolls along the scenic riverfront, perfect for relaxation and people-watching.
  • Diverse Shopping Districts: Explore a variety of shopping options, from high-end boutiques to unique local shops.
  • Family-Friendly Activities: Engage in numerous activities suitable for all ages, ensuring fun for the whole family.
  • Lively Nightlife: Experience the energetic nightlife with a plethora of bars, clubs, and entertainment venues.

Popular types of accommodation around Near North Side

If you’re exploring vacation rentals in Near North Side, you’ll find a variety of popular accommodations to suit your needs. From stylish downtown Chicago apartments to cozy studio apartments, there’s something for everyone. Whether you prefer a private vacation home or a modern condo, our selection includes options like Cicero and Lincolnwood apartments for those seeking a unique experience. Enjoy transparency, savings, and reassurance as you plan your stay.

  • Apartments: These are the top choice for vacation rentals in Near North Side, offering a comfortable and convenient stay in urban settings.
  • Houses: Ideal for families or groups, these homes provide a homely atmosphere with plenty of space and amenities.
  • Condos: A popular option that combines the benefits of apartment living with resort-style amenities for a delightful experience.
  • Cottages: Perfect for a quaint getaway, these charming spaces offer a cozy retreat from the bustling city.
  • Villas: Luxurious and spacious, villas offer an upscale experience for travelers seeking comfort and elegance.**

Top attractions near Near North Side

Near North Side in Chicago is perfect for family vacations and outdoor adventures, offering a vibrant city atmosphere. Explore iconic skyscrapers, bustling streets, and beautiful urban parks. This area caters to travelers seeking cultural experiences and family-friendly activities, ensuring there’s something for everyone to enjoy during your visit. Don't miss out on the diverse attractions that make Near North Side a must-see destination.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street is lined with upscale shops, restaurants, and iconic architecture, offering a quintessential Chicago experience just 0.8 miles from Near North Side.
  • Navy Pier: A bustling entertainment hub located 2 miles away, Navy Pier features stunning waterfront views, amusement rides, dining options, and seasonal activities, all in a friendly atmosphere.
  • Millennium Park: Just 1 mile from Near North Side, this urban oasis boasts beautiful gardens, public art installations, and concert venues, making it perfect for families and outdoor enthusiasts.

Things to do recommended for couples

Embark on a romantic getaway in Near North Side, Chicago. Enjoy live music at House of Blues, savor a meal at the charming Historic Michael Jordan Restaurant, or catch a concert at the Aragon Ballroom. Each experience promises unforgettable moments for couples.

Things to do recommended for families

Families will love the excitement at Wrigley Field, just 4 miles away, while Northerly Island Natural Area offers a serene escape 3 miles from Near North Side. For relaxation, The East Bank Club is conveniently located only 0.8 miles away, perfect for unwinding together.

Things to do recommended for groups

Groups visiting Near North Side can enjoy a captivating show at the historic Chicago Theatre, share laughs at the famous Second City comedy club, and indulge in shopping at Chicago Place Mall, all within a short distance, creating memorable experiences for everyone in the group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Near North Side

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Near North Side with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Near North Side with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Near North Side: For many, a family vacation isn't truly a vacation without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Near North Side: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Near North Side

Near North Side offers an exciting blend of urban charm and family-friendly attractions. Explore the vibrant downtown Chicago, stroll along the scenic riverfront, and dive into diverse shopping districts. Enjoy the lively nightlife scenes and discover distinct neighborhoods, each with its unique vibe. Whether you're seeking adventure or relaxation, Near North Side is the perfect base for a memorable vacation experience.

  • Chicago: Chicago is a bustling metropolis that serves as the heart of the Near North Side. Known for its rich cultural scene and vibrant neighborhoods, the city offers a plethora of family-friendly activities and outdoor experiences. Visitors can explore renowned shopping areas, catch a game at local sports facilities, and enjoy a variety of arena entertainment options. The city's landmarks, including iconic stadiums and tourist precincts, make it a must-visit destination for anyone looking to immerse themselves in urban life.
  • Downtown Chicago: Located just 1 mile from Near North Side, Downtown Chicago is a vibrant neighborhood that encapsulates the city's dynamic spirit. Ideal for families and outdoor enthusiasts, Downtown boasts a mix of shopping areas, theaters, and arena entertainment. Visitors can enjoy stunning views of the skyline, partake in cultural events, and explore local attractions like sports facilities and tourist precincts. With its convenient location and lively atmosphere, Downtown Chicago is perfect for those looking to experience the best the city has to offer.
  • Magnificent Mile: Just 0.6 miles away from Near North Side, the Magnificent Mile is a world-renowned shopping district that combines luxury with a vibrant city experience. Families and city explorers will delight in the array of shopping options, educational attractions, and outdoor spaces. This iconic neighborhood features stunning architecture, bustling streets, and easy access to arena entertainment, making it a prime location for visitors. With its close proximity to tourist precincts and sports facilities, the Magnificent Mile is an essential stop for anyone looking to experience Chicago's charm.

Best time to go to Near North Side

If you're planning a trip to Near North Side, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in February to March and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately HighSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyModerately HighSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyModerately LowAverage
November42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in even greater savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your total booking. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash on eligible bookings. Sign up today and start enjoying the savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is designed to help you plan your travels with ease. You can create new trips, manage your ongoing plans, or review and organize your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Near North Side?
In Near North Side, apartments are the most popular type of vacation rental, with about 38 available in this vibrant area. These apartments are typically situated close to key attractions like the Magnificent Mile and Lake Michigan, providing easy access to shopping, dining, and entertainment. Most units come equipped with fully functional kitchens, comfortable living spaces, and often feature amenities such as fitness centers and rooftop terraces for enjoying city views. For those seeking more space, there are around 12 vacation houses available, which usually offer multiple bedrooms, private outdoor areas, and additional comforts, making them ideal for families or groups traveling together.
Are there any beach house rentals in Near North Side?
In Near North Side, Illinois, there are several beach house rentals available, primarily concentrated along the shoreline of Lake Michigan. These properties often feature spacious living areas, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor patios for enjoying the lakeside atmosphere. Many rentals are located near popular attractions like Oak Street Beach and the vibrant shops and restaurants of the Magnificent Mile, making them ideal for travelers looking to experience both relaxation and urban excitement.
How much does it cost to rent a vacation home in Near North Side?
Prices for vacation rentals in Near North Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Near North Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Near North Side vacation house rentals?
You can find great discounts on house rentals in Near North Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Near North Side?
In Near North Side, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy the convenience of home dining. Many rentals also feature coffee and tea makers for a quick morning brew. Pet-friendly options are available, accommodating travelers with furry companions, while service animals are permitted as well. Additionally, fitness facilities are offered in several properties, suiting those who want to maintain their workout routines during their stay.
Can I find family house rentals in Near North Side?
In the Near North Side of Chicago, there are around 20 family-friendly house rentals available, making it an excellent choice for groups traveling together. This vibrant neighborhood is known for its proximity to popular attractions such as Lincoln Park, the Chicago Riverwalk, and the bustling Magnificent Mile.

Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play or families can gather. Amenities like Wi-Fi, air conditioning, and laundry facilities are commonly included, ensuring a comfortable and convenient stay for visitors.

With its rich cultural offerings, including museums and theaters, as well as easy access to public transportation, families can enjoy both relaxation and exploration in this dynamic area of the city.
Can I rent a vacation home with a pool or hot tub in Near North Side?
In the Near North Side of Chicago, there are several vacation homes available for rent that feature both pools and hot tubs. This vibrant neighborhood, known for its proximity to Lake Michigan and the bustling city life, offers a variety of accommodations suitable for travelers seeking relaxation and luxury. Many of these rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for entertaining or unwinding after a day of exploration.
Are there any Near North Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Near North Side with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Near North Side?
In the Near North Side of Chicago, there are numerous pet-friendly vacation rentals available, with a total of 26 options to choose from. This vibrant area features a variety of accommodations, including modern apartments and spacious condos, often equipped with amenities such as full kitchens, high-speed internet, and access to fitness centers or rooftop terraces.

Pet owners will appreciate the proximity to several parks, including the expansive Lincoln Park, which offers walking trails, gardens, and even the Lincoln Park Zoo, providing plenty of outdoor space for pets to enjoy. Additionally, the neighborhood is home to various pet-friendly cafes and shops, ensuring that both you and your furry companions can have a delightful stay. See all pet-friendly rentals in Near North Side.
Can I find long-stay vacation rentals in Near North Side?
A long-stay vacation rental in Near North Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Near North Side for a vacation rental?
The best time to visit Near North Side is during the peak season from February to April, with March being particularly popular. This vibrant period attracts travelers eager to experience the lively option of the city as winter transitions to spring. Visitors can enjoy a number of outdoor activities, including leisurely strolls along the scenic lakefront and engaging in cultural experiences at nearby museums and galleries.

During this time, temperatures typically range from the low 40s to mid-60s Fahrenheit, creating a comfortable climate for sightseeing and exploring the charming neighborhoods. The blooming flowers in parks and gardens add to the area's appeal, making it an ideal setting for photography and relaxation.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to enjoy the local culture without the hustle and bustle of peak tourist activity. The cooler temperatures in the 30s to 50s Fahrenheit create a cozy atmosphere, superb for indulging in the city's renowned coffee shops and cozy eateries.
Are there any remote work vacation rentals in Near North Side?
In the Near North Side of Chicago, there are numerous vacation rentals suitable for remote work, with about 26 options available. This vibrant neighborhood, known for its proximity to Lake Michigan and bustling cultural attractions, offers a variety of accommodations that cater to professionals looking to combine work and leisure. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace with desks and ergonomic chairs, and comfortable living areas conducive to productivity.

Travelers can expect easy access to popular points of interest like the Magnificent Mile, the Lincoln Park Zoo, and various dining and shopping options, making it an ideal location for both work and relaxation. Additionally, some properties may include features like kitchen facilities for convenient meal preparation and areas to unwind after a busy day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Near North Side vacation rental?
Book your Near North Side vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Near North Side, Illinois, United States of America?
In the Near North Side of Chicago, visitors can explore a variety of attractions that reflect the vibrant culture and history of the area. The Magnificent Mile, a famous shopping district along Michigan Avenue, offers an array of upscale shops, restaurants, and iconic buildings such as the John Hancock Center, where travelers can enjoy panoramic views of the city from its observation deck.

Just south of the Magnificent Mile, River North is known for its art galleries and nightlife, making it a popular destination for those looking to experience Chicago's dynamic art scene. The Museum of Contemporary Art is located nearby, showcasing thought-provoking exhibitions and performances.

For those interested in history and architecture, the historic Water Tower and the Chicago Riverwalk provide picturesque settings for leisurely strolls and photography. Additionally, the Near North Side is home to the beautiful Oak Street Beach along Lake Michigan, where visitors can relax and enjoy the waterfront.
Can I change or cancel my Near North Side home rental booking on Vrbo?
To find Near North Side vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Near North Side vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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