Near North Side vacation rentals

We found 1,136 vacation rentals — enter your dates for availability

Discover a selection of 463 apartments, 27 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.

Vacation rentals with weekly discounts - Near North Side

Showing deals for:Dec 26 - Jan 2

Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town

Room
10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Luxury SOHO Styled Two-Level Townhouse - Old Town

Chicago, IL

9% off
Price is $949
$6,643 for 7 nights
All fees included
Luxury SOHO Styled Two-Level Townhouse - Old Town

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Find out more about Near North Side

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 33 available in vibrant neighborhoods close to attractions like the Magnificent Mile and Oak Street Beach. These apartments typically feature modern amenities, including fully equipped kitchens, comfortable living areas, and often in-unit laundry facilities. For those seeking a bit more space, there are around 12 vacation houses that cater to families or groups. These homes generally offer multiple bedrooms, private outdoor spaces, and convenient parking options, making them ideal for longer stays.
Are there any beach house rentals in Near North Side?
In Near North Side, Illinois, there are about 10 beach house vacation rentals available. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups. Many rentals offer outdoor spaces, such as patios or balconies, to enjoy the views of Lake Michigan and the vibrant city atmosphere.
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 cater to travelers looking for comfort and convenience. Many rentals feature fully equipped kitchens, allowing guests to prepare meals at their leisure. Additional amenities often include coffee and tea makers for those who enjoy a morning brew, kitchen islands for extra workspace, and blenders for making smoothies or cocktails. For families traveling with young children, many properties also provide travel cribs, ensuring a comfortable stay for little ones.
Are there any family house rentals in Near North Side?
In the Near North Side of Chicago, there are numerous family-friendly house rentals available, with around 32 options to choose from. This vibrant area is known for its mix of cultural attractions, dining, and parks, making it ideal for families. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor spaces, superb for gathering after a day of exploring the city.

Amenities such as Wi-Fi, air conditioning, and laundry facilities are often included, ensuring a comfortable stay for visitors. Families can enjoy easy access to nearby points of interest, like Lincoln Park Zoo, where kids can marvel at the animals, and the beaches along Lake Michigan, which offer sand and sun activities.
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 come equipped with pools and hot tubs. This vibrant neighborhood is known for its proximity to the beautiful shores of Lake Michigan and a variety of cultural attractions. Travelers can find properties that often feature private pools, hot tubs, and outdoor spaces superb for relaxation and entertainment. Many rentals are also equipped with modern kitchens, spacious living areas, and amenities like Wi-Fi and air conditioning, ensuring a comfortable stay.
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.
Are there pet-friendly vacation rentals in Near North Side?
In the Near North Side of Chicago, travelers can find a variety of pet-friendly vacation rentals to suit their needs, with around 17 options available. This vibrant area is known for its proximity to iconic attractions and lush parks, making it an ideal spot for those traveling with pets. Many of the rentals here offer modern amenities, such as fully equipped kitchens, comfortable living spaces, and sometimes even outdoor patios or balconies where pets can enjoy fresh air.

Notably, the Lincoln Park area is nearby, featuring expansive green spaces where pets can roam freely. The park includes walking trails and gardens, providing a great environment for leisurely strolls with your furry companions. Additionally, the neighborhood is home to pet-friendly cafes, shops, and even the Lincoln Park Zoo, which can be a delightful outing for both pets and their owners.

Moreover, the proximity to Lake Michigan offers scenic waterfront paths superb for longer walks or jogs with pets.
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?
March is the most popular time to visit Near North Side, Illinois, as the city begins to awaken from winter and welcomes a vibrant array of activities. The peak season extends from February to April, attracting travelers eager to experience the area's cultural events and lively atmosphere. This period is marked by comfortable spring temperatures, typically ranging from the upper 30s to low 60s Fahrenheit, making it ideal for outdoor sightseeing and exploring the unique neighborhoods.

During this peak season, visitors can enjoy a variety of events, including art fairs, food festivals, and the excitement of St. Patrick's Day celebrations. The blossoming parks and gardens provide an inviting backdrop for leisurely strolls, while the close proximity to attractions like the Magnificent Mile and Navy Pier ensures plenty of options for adventure and relaxation.

If you're looking for a more budget-friendly time to visit, consider planning your trip in November. This month offers a quieter atmosphere and a chance to experience the city's charm without the hustle and bustle of peak tourist season. You can explore local shops, indulge in seasonal cuisine, and soak in the sights at a more leisurely pace.

Ultimately, the best time to book a vacation rental in Near North Side depends on your preferences for vibrant energy and cultural experiences in the spring or the peaceful exploration of the fall.
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 around 34 options available. This vibrant neighborhood is known for its proximity to Lake Michigan, cultural attractions, and bustling city life. Many of these rentals cater specifically to remote workers, offering amenities such as high-speed WiFi, dedicated office spaces with desks and chairs, and even additional features like computer monitors and safes for secure storage.

Travelers can expect to find modern apartments and condos that often include comfortable living areas, fully equipped kitchens, and access to fitness centers or rooftop lounges. The area boasts easy access to public transportation, making it convenient for those who may want to explore downtown Chicago during breaks. Additionally, local coffee shops and co-working spaces are just a stone's throw away, providing alternative work environments and networking opportunities. 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?
In Near North Side, visitors can enjoy a variety of top attractions. The iconic Magnificent Mile, known for its shopping, dining, and entertainment options, runs through this vibrant neighborhood. Here, travelers can find luxury boutiques, popular department stores, and a selection of restaurants offering diverse cuisines.

The area is also home to Navy Pier, where guests can partake in a range of activities, including rides, exhibitions, and dining with waterfront views. For art enthusiasts, the Museum of Contemporary Art is located nearby, showcasing innovative works and hosting engaging events.

Further along, the historic Chicago Water Tower provides a glimpse into the city's past and is a popular photo spot. Additionally, the beautiful Oak Street Beach offers a relaxing retreat by the lake, ideal for sunbathing and enjoying water sports during warmer months.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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