Photo by Deano
Near East Side holiday rentals
We found 946 holiday rentals — enter your dates for availability
Discover a selection of 13 apartments and other holiday rentals in Near East Side that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as parking and a TV. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Near East Side
Showing deals for:3 Oct - 10 Oct
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$12,757
AU$12,757
AU$1,822 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is AU$8,200
AU$8,200
AU$1,171 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$6,663
AU$6,663
AU$952 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,856
AU$3,856
AU$551 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is AU$6,189
AU$6,189
AU$884 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
8% off
Price is AU$10,568
AU$10,568
AU$1,510 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is AU$6,417
AU$6,417
AU$917 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is AU$5,908
AU$5,908
AU$844 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is AU$13,468
AU$13,468
AU$1,924 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$6,435
AU$6,435
AU$919 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is AU$11,260
AU$11,260
AU$1,609 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is AU$7,603
AU$7,603
AU$1,086 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is AU$11,253
AU$11,253
AU$1,608 per night
includes taxes & fees
Image gallery for #1901 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(57 reviews)
#1901 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$6,663
AU$6,663
AU$952 per night
includes taxes & fees
Image gallery for #1402 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(25 reviews)
#1402 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$6,663
AU$6,663
AU$952 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse North - Pool - Gold Coast
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxury Designer Penthouse North - Pool - Gold Coast
Chicago, Illinois
8% off
Price is AU$10,081
AU$10,081
AU$1,440 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$4,581
AU$4,581
AU$654 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(18 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is AU$12,318
AU$12,318
AU$1,760 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(17 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$4,581
AU$4,581
AU$654 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$6,018
AU$6,018
AU$860 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$5,762
AU$5,762
AU$823 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$4,581
AU$4,581
AU$654 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$12,121
AU$12,121
AU$1,732 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,856
AU$3,856
AU$551 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Near East Side
Showing deals for: 3 Oct - 6 Oct
Group Vacation! 2 Spacious Units Near Oak Street Beach! Onsite Parking!
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$3,749
AU$3,749
for 3 nights, 1 home
AU$1,250 per night
includes taxes & fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sleeps 2 · 1 bedroom
8.28.2 out of 10
Very goodvery good
167 reviews(167 reviews)
The current price is AU$1,196
AU$1,196
for 3 nights, 1 room
AU$399 per night
includes taxes & fees
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
77 reviews(77 reviews)
The current price is AU$1,538
AU$1,538
for 3 nights, 1 room
AU$513 per night
includes taxes & fees
Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is AU$1,649
AU$1,649
for 3 nights, 1 home
AU$550 per night
includes taxes & fees
Downtown Retreat: 2BR, Balcony, Resort Comfort
Sleeps 7 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is AU$3,780
AU$3,780
for 3 nights, 1 apartment
AU$1,260 per night
includes taxes & fees
Beautiful Unit CHI in Prime River North - 2
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
The current price is AU$3,837
AU$3,837
for 3 nights, 1 apartment
AU$1,279 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Near East Side?
Apartments are the most popular type of holiday home in Near East Side, according to our data. Even if you have a different idea about what you want, Stayz has properties in many sizes and shapes. Compare our options to find your perfect Near East Side pad.
How much does it cost to rent a holiday home in Near East Side?
A number of factors determine how much you pay for a holiday home in Near East Side, including the time of year, property type and length of stay. But, all Stayz homes have something in common --- unbeatable value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Near East Side?
The average price for a holiday home by the beach in Near East Side will depend on when you'll be there and the size and style of property you're looking for. Find prices quickly and easily on Stayz by entering your dates of travel. Then use our filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Near East Side?
Pack a travel bag and a bone for your pooch because Near East Side has five holiday homes that throw open their doors to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Near East Side?
Add an extra layer of fun to your getaway by booking one of the five houses with a private pool in Near East Side. Use our search filter to find the kind of property you want on Stayz, and then spend lazy days splashing and playing in a swimming pool that's for your exclusive use.
What are popular home amenities in Near East Side?
When it comes to home amenities that people search for in Near East Side, a lake view, a swimming pool and a sauna are at the top of the list. With Stayz holiday homes, you'll find options to fit your style and taste, whether you're holidaying with relatives, friends or even pets.
Are there large group holiday homes in Near East Side?
Take your pick of five Stayz holiday homes in Near East Side that can accommodate five or more people. You'll get all the privacy and room you need to have fun with your loved ones --- and no one else.
Are there holiday homes in Near East Side that welcome kids?
Gather your entire family for a fun-packed adventure in Near East Side at one of our five family-friendly holiday homes. These stays provide amenities that are just perfect for trips with the kids, like laundry facilities, living rooms and patios. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Near East Side?
Keeping the kids amused during your Near East Side holiday is a breeze with these awesome family-friendly attractions:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there holiday homes with WiFi in Near East Side?
Near East Side has five holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a cinch to get online.
How can I find holiday homes with air conditioning in Near East Side?
You can choose from five Stayz holiday homes with air conditioning in Near East Side providing that cool, cool breeze and extra bit of comfort. Enter your desired travel dates and then use our handy filters to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Near East Side?
The minimum age is normally 16, 18 or 21. It can change between properties on Stayz, so look at the rules of your preferred Near East Side holiday home before booking.
How long can I rent a holiday home in Near East Side for?
It's really down to the Near East Side property. To look at a list of options offering extended stays, simply type your dates and number of people into Stayz. Enjoy having the place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space to run around in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.