Magnificent Mile - River North featuring street scenes, night scenes and signage

Near North Side holiday rentals

We found 1,142 holiday rentals — enter your dates for availability

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September 2025

October 2025

Discover a selection of 529 apartments, 29 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:5 Dec - 12 Dec

Loft Living Space with Deep, Comfortable Sofa, Smart Flat Screen TV & Fireplace

Exceptional

(50 reviews)

Luxury House in the heart of Old Town with Parking

Chicago, IL

11% off

for 7 nights, 1 home

S$2,546 nightly

Includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(58 reviews)

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

S$627 nightly

Includes taxes & fees

Huge, well designed condo that provides plenty of space and comfort!

Exceptional

(16 reviews)

River North 3BR/2BA: HUGE, Parking, Center Chicago

Chicago, IL

7% off

for 7 nights, 1 apartment

S$1,123 nightly

Includes taxes & fees

Enter into our large 1800 sq. ft. condo, featuring a game room. Perfect for you!

Exceptional

(29 reviews)

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, IL

11% off

for 7 nights, 1 apartment

S$1,028 nightly

Includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(30 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

S$468 nightly

Includes taxes & fees

Wonderful

(35 reviews)

Spectacular Corner 2BR Penthouse in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

S$662 nightly

Includes taxes & fees

Living Room / Dining Room with Fully stocked kitchen

Living Room has pullout couch (denim colored sofa)

Wonderful

(5 reviews)

Historic and Unique Brownstone in Gold Coast - 3

Chicago, IL

13% off

for 7 nights, 1 apartment

S$175 nightly

Includes taxes & fees

Exceptional

(6 reviews)

East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.

Chicago, IL

6% off

for 7 nights, 1 apartment

S$718 nightly

Includes taxes & fees

Exceptional

(7 reviews)

Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Chicago, IL

7% off

for 7 nights, 1 apartment

S$619 nightly

Includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Near North Side

Navy Pier

Find the best place to stay - Near North Side

Kasa Magnificent Mile Chicago

Sleeps 3 · 1 bedroom

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Sleeps 22 · 5 bedrooms · 3+ bathrooms

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

What is the most popular type of holiday rental accommodation in Near North Side?

Apartments are the most popular style of holiday rental in Near North Side, according to our data. Even if you have something different in mind, Vrbo has properties in all sizes and shapes. Explore our options to find your perfect match.

How much does it cost to rent a holiday rental 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 Vrbo holiday rentals 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 Vrbo 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 rentals in Near North Side?

Yes, there are. You'll have your pick of 429 holiday rentals that cater to pets in Near North Side. Some of our pet-friendly holiday rentals 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 Vrbo.

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 Vrbo, then spend your downtime frolicking in a swimming pool that's all your own.

What are popular rental amenities in Near North Side?

A lake view, a fireplace and a water view are rated the most popular rental amenities in Near North Side. Whether you're heading away on your own, with your sweetheart or as a family group, Vrbo can help you find a holiday rental that matches your tastes with all the extras you're looking for.

Are there large group holiday rentals in Near North Side?

With 42 holiday rentals 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, Vrbo will help you find a large group rental to suit the occasion.

Are there holiday rentals 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 rentals 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 rentals 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 Vrbo.

Are there holiday rentals with WiFi in Near North Side?

Near North Side has 64 holiday rentals 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 Vrbo homes make it easy to go online.

How can I find holiday rentals with air conditioning in Near North Side?

Pick your travel dates and then make use of the filters to locate holiday rentals with ac in Near North Side on Vrbo. 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 rental in Near North Side?

You should check with the Near North Side holiday home you'd like on Vrbo as age restrictions differ. However, it's typically 16, 18 or 21.

How long can I rent a holiday rental in Near North Side for?

How long you can book a holiday rental 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.