Photo by TM

Near North Side holiday rentals

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.

Holiday rentals with weekly discounts – Near North Side

Showing deals for:25 Dec - 1 Jan

Living area
Terrace/patio
Living area
Private kitchen
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$20,878
for 7 nights, 1 apartment
AU$2,983 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Room
Our downtown Townhouse is in an amazing location
Interior
Dining
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$18,649
for 7 nights, 1 home
AU$2,664 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$10,270
for 7 nights, 1 home
AU$1,467 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Private kitchen
Living area
Exterior
Room
Exceptional
(113 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,619
for 7 nights, 1 home
AU$1,088 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Interior
Interior
Dining
Room
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$10,885
for 7 nights, 1 home
AU$1,555 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Kitchen (upstairs)
Downstairs living area
Upstairs queen bedroom 2
Fun Mirror Wall Upstairs
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$13,147
for 7 nights, 1 apartment
AU$1,878 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Exterior
Room
Private kitchen
Exceptional
(35 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,661
for 7 nights, 1 apartment
AU$1,237 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Private kitchen
Living area
Exterior
Living area
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
AU$4,357
for 7 nights, 1 apartment
AU$622 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

  • 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

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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Near North Side holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Near North Side to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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