Near North Side holiday homes

We found 1,155 holiday rentals — enter your dates for availability

Discover a selection of 468 apartments, 27 flats and other holiday rentals in Near North Side that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Near North Side

Showing deals for:19 Dec - 26 Dec
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Why visit Near North Side

  • Stunning skyline views: Experience breathtaking vistas of the iconic Chicago skyline from various vantage points, including observation decks.
  • Family-friendly activities: Enjoy a range of cultural experiences and outdoor adventures suitable for all ages.
  • Vibrant nightlife: Explore the lively streets of Near North Side, filled with bustling bars, restaurants, and entertainment options.
  • Urban parks: Relax in scenic urban parks that offer green spaces for picnics and play.
  • Welcoming atmosphere: Experience the warmth of friendly locals who make you feel right at home.

Top attractions near Near North Side

Near North Side in Chicago is perfect for a family getaway, offering a mix of urban parks, towering skyscrapers, and vibrant streets. You'll find plenty of cultural experiences and activities suitable for the whole family. Explore nearby neighbourhoods, take in the stunning Chicago skyline, enjoy events along the Chicago River, and visit the observation deck for breathtaking views. This area promises unforgettable adventures for every traveller.

  • Navy Pier: A vibrant jetty offering stunning views of Lake Michigan, diverse dining options, and a lively atmosphere perfect for a leisurely stroll or enjoying local events.
  • John Hancock Center: This iconic skyscraper features a breathtaking observation deck with panoramic views of the city skyline and Lake Michigan, providing a unique perspective of Chicago.
  • North Avenue Beach: A beautiful stretch of sandy beach ideal for sunbathing, swimming, and beach sports, with a relaxed vibe and scenic views of the city.

Things to do recommended for couples

For a romantic getaway in Near North Side, Chicago, explore the lively House of Blues for a concert, indulge in a meal at the charming Historic Michael Jordan Restaurant, or catch a show at the Aragon Ballroom. Each offers a unique vibe for couples to enjoy together.

Things to do recommended for families

Families can catch a game at Wrigley Field or Soldier Field, both offering a vibrant sports atmosphere. For a more relaxing outing, head to the Northerly Island Natural Area, where you can enjoy nature and unwind just a stone's throw from Near North Side.

Things to do recommended for groups

Enjoy a night out at the Chicago Theatre, just 1.6km away, for a dose of culture and entertainment. For some laughs, head to Second City, 1.3km away, or shop at Chicago Place Mall, only 966m from your base. Perfect for a fun group outing.

*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 heading off on a trip with a group, family, or pets, or if you're in search of extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Near North Side with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Near North Side with young kids: Traveling with young kids can be quite the task. You'll want to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. It's also wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Near North Side: For many families, a holiday isn’t quite right without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with 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 holiday rentals with special offers 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 accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Near North Side

Near North Side, Chicago, offers a vibrant mix of urban charm and scenic beauty, perfect for families and outdoor enthusiasts. Explore the lively downtown area, stroll along Chicago Avenue, and soak up the bustling nightlife. This neighbourhood is not just about the city buzz; it’s also a welcoming spot where friendly locals create a warm atmosphere. Discover the best of urban living while enjoying picturesque views and unique experiences just a stone’s throw from the city centre.

  • Chicago: As the third-largest city in the United States, Chicago is a vibrant urban hub that perfectly blends culture, history, and modern attractions. Located in the heart of the Midwest, the Near North Side is a prime location for exploring the city's famous skyline, diverse neighborhoods, and stunning waterfront along Lake Michigan. Visitors can indulge in world-class shopping, experience live performances at renowned theatres, or cheer for their favourite teams at iconic sports facilities. With a variety of family-friendly activities and outdoor spaces, Chicago provides an unforgettable experience for all types of travellers.
  • Downtown Chicago: just 1.6km from Near North Side, Downtown Chicago pulsates with energy and excitement. This dynamic neighbourhood is the city's commercial and cultural centre, where tourists can enjoy a wealth of attractions, from the magnificent Art Institute to the lively Millennium Park. Downtown is also home to an array of shopping options and dining experiences, catering to every palate. The area's stunning architecture, bustling streets, and vibrant nightlife make it an ideal spot for families and urban explorers alike.
  • Magnificent Mile: Located a mere 966m from Near North Side, the Magnificent Mile is Chicago's premier shopping and entertainment district. This iconic stretch along Michigan Avenue boasts an impressive array of high-end shops, department stores, and dining establishments. Visitors can also explore cultural landmarks, such as the historic Water Tower and the John Hancock Center. With its lively atmosphere and stunning views, the Magnificent Mile offers a perfect blend of family-friendly activities and city-themed attractions for an enjoyable day out.

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.

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

Booking with Vrbo is simple

Are you keen to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to narrow down options by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy space for you to plan new getaways, continue from where you last stopped, or manage your travel arrangements. You can easily find the properties you’ve saved or booked, sorted into Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Near North Side?
Apartments are the most popular style of holiday home in Near North Side, according to our data. Even if you have something different in mind, Bookabach has properties in all sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday home in Near North Side?
Length of stay, property type and time of year are some factors that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From cosy chalets to sprawling luxury villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Near North Side?
Prices for beach houses in Near North Side can vary depending on the size and style of the property and time of year you're travelling. Just enter your travel dates into Bookabach and how many guests to view available options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Near North Side?
Yes, there are. You'll have your pick of 429 holiday homes that cater to pets in Near North Side. Some of our pet-friendly holiday homes come with an outdoor space for your fur child to run around in, complimentary treats, doggie beds and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Bookabach.
Can I rent a house with a pool in Near North Side?
Add a whole other level of fun to your getaway by staying in one of the 103 houses with a private pool in Near North Side. Use our search filter to find properties with pools on Bookabach, then spend your downtime frolicking in a swimming pool that's all your own.
What are popular home amenities in Near North Side?
A lake view, a fireplace and a water view are rated the most popular home amenities in Near North Side. Whether you're heading away on your own, with your sweetheart or as a family group, Bookabach can help you find a holiday home that matches your tastes with all the extras you're looking for.
Are there large group holiday homes in Near North Side?
With 42 holiday homes that can host 10 guests or more in Near North Side, there's no need to cross anyone off the invite list. From extended family holidays to special events like Christmas and birthday parties, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes in Near North Side that welcome kids?
With 428 family-friendly holiday properties to choose from in Near North Side, now is an awesome time to introduce the kiddos to the wonders of travel. Simply check our "Properties good for families" filter box to search for stays loaded with amenities perfect for travelling families, such as dining rooms, backyards, hot tubs and entertainment areas.
What are the top attractions for families in Near North Side?
Keep your kids occupied at these top family-friendly attractions in Near North Side:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Near North Side?
Yes, there are 169 one-bedroom properties in Near North Side to pick from. A one-bedroom holiday home is a great choice if it's just the two of you or if you're travelling solo. Throw in more privacy, convenience and space compared to a standard hotel, and you're sure to have a break to remember.
Can I find two-bedroom holiday homes in Near North Side?
Near North Side has 100 two-bedroom holiday properties for you to select from. Experience a holiday home with all the privacy and comfort you're looking for at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Near North Side?
Near North Side has 64 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Near North Side?
Pick your travel dates and then make use of the filters to locate holiday homes with ac in Near North Side on Bookabach. With 418 air-conditioned properties to choose from here, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday home in Near North Side?
You should check with the Near North Side holiday home you'd like on Bookabach as age restrictions differ. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Near North Side for?
How long you can book a holiday home in Near North Side is up to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With loads of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover a terrific place to call your home away from home in Near North Side.

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