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Near North Side holiday homes

We found 1,051 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Near North Side by choosing from 29 houses, 438 apartments and other holiday rentals. 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.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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

When is the best time to visit Near North Side for a holiday rental?
The most popular time to visit Near North Side is from February to April, coinciding with the vibrant energy of spring. This peak season attracts a diverse range of travellers eager to enjoy the city's culture, art, and culinary delights. As the weather warms up, temperatures typically range from about 1 to 15 degrees Celsius, providing a comfortable climate for outdoor activities and sightseeing.March, in particular, stands out as a highlight, with events like St. Patrick's Day parades and various festivals that add to the lively option. Visitors can easily explore the area's iconic attractions, such as the Magnificent Mile, Millennium Park, and the renowned Art Institute of Chicago, all while enjoying the blossoming scenery.For those looking for a more budget-friendly option, November offers a quieter experience with fewer tourists. This month allows you to enjoy the city's charm without the crowds, making it an excellent time for leisurely strolls through local parks or exploring neighbourhood cafes.Ultimately, the best time to book a holiday rental in Near North Side depends on your preference for vibrant events and social experiences in peak season or the tranquil enjoyment of the city in the shoulder months.
What are the top attractions in Near North Side, Illinois, United States of America?
In Near North Side, Chicago, visitors can enjoy a range of attractions that highlight the area's vibrant culture and rich history. The Magnificent Mile is a major draw, offering an array of high-end shops, restaurants, and iconic landmarks like the John Hancock Centre, where guests can take in stunning views from the observation deck.The area is also home to Navy Pier, a popular entertainment destination featuring rides, dining options, and beautiful views of Lake Michigan. For those interested in art and culture, the Museum of Contemporary Art is located nearby, showcasing an impressive collection of modern art and hosting various exhibitions and events.Additionally, the historic Old Town neighbourhood, just a short walk away, is famous for its charming architecture, lively option, and attractions like the Old Town Triangle Historic District, providing a glimpse into Chicago's past.
Are all fees included in the Near North Side holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Near North Side holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Near North Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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 any discounts for Near North Side holiday homes?
You can find great discounts on holiday homes in Near North Side on Bookabach, 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.
Can I change or cancel my Near North Side holiday home booking on Bookabach?
To find Near North Side holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Near North Side?
A long-stay holiday home in Near North Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Near North Side holiday home?
Book your Near North Side holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Near North Side?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Near North Side to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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