Apartment
8.4(11 Reviews)
1 Bedroom
2 Guests
Kitchen
Air Conditioner
Internet
Pet Friendly
US $192/Night
7 Nights - US $1,343
North Side, IL Holiday Rentals
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Compare Villas, Resorts, & Rentals in North Side
8.4
Apartment
10.0(14 Reviews)
1 Bedroom
2 Guests
- Internet
Child Friendly
Security/Safety
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0(566 Reviews)
1 Bedroom
Parking
Balcony/Terrace- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,364
Apartment
10.0(161 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $260/Night
7 Nights - US $1,822
Apartment
10.0(4 Reviews)
6 Bedrooms
20 Guests
Private Beach
EV Charge Station- Parking
Ocean View
US $482/Night
7 Nights - US $3,371
House
10.0(152 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,099/Night
7 Nights - US $7,696
Condo
10.0(140 Reviews)
3 Bedrooms
10 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $499/Night
7 Nights - US $3,490
Apartment
10.0(120 Reviews)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $731/Night
7 Nights - US $5,119
Apartment
10.0(105 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $196/Night
7 Nights - US $1,372
Luxury Holiday Rentals in North Side
Over 1270+ Luxury Holiday Rentals in or Near North Side
House
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,672/Night
7 Nights - US $25,705
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
View- Kitchen
US $2,937/Night
7 Nights - US $20,561
House
5 Bedrooms
15 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $2,266/Night
7 Nights - US $15,859
Apartment
10.0(15 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,108/Night
7 Nights - US $14,757
House
9.5(2 Reviews)
4 Bedrooms
12 Guests
- Parking
- View
- Air Conditioner
- Internet
US $2,066/Night
7 Nights - US $14,462
House
10.0(63 Reviews)
6 Bedrooms
17 Guests
- Hot Tub
- Parking
Spa- Ocean View
US $1,969/Night
7 Nights - US $13,782
House
10.0(71 Reviews)
5 Bedrooms
12 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $1,961/Night
7 Nights - US $13,725
New
Apartment
10.0(2 Reviews)
9 Bedrooms
16 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $1,927/Night
7 Nights - US $13,489
House
7.4(3 Reviews)
9 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,877/Night
7 Nights - US $13,138
Top-Rated Holiday Rentals with a Pool in North Side
Over 33+ The Best Private Villas and Holiday Rentals in North Side with a Pool
Hotel
10.0(9 Reviews)
Pool- Kitchen
- Air Conditioner
- Internet
US $276/Night
7 Nights - US $1,930
Bed & Breakfast
9.8(110 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $434/Night
7 Nights - US $3,037
Hotel
9.6(7 Reviews)
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $258/Night
7 Nights - US $1,807
US $473/Night
7 Nights - US $3,314
Resort
8.5(142 Reviews)
6 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $503/Night
7 Nights - US $3,522
Apartment
10.0(3 Reviews)
3 Bedrooms
13 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $913/Night
7 Nights - US $6,392
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,358
Apartment
9.8(45 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $338/Night
7 Nights - US $2,369
House
8.8(6 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $596/Night
7 Nights - US $4,171
Pet-Friendly Holiday Rentals in North Side
Over 526+ Pet-Friendly Holiday Rentals in or Near North Side
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $353/Night
7 Nights - US $2,473
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $832/Night
7 Nights - US $5,827
Bed & Breakfast
8.2(687 Reviews)
1 Bedroom
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $143/Night
7 Nights - US $998
Apartment
10.0(98 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,017
Apartment
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $667/Night
7 Nights - US $4,672
House
10.0(56 Reviews)
6 Bedrooms
20 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $403/Night
7 Nights - US $2,823
Apartment
10.0(56 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $203/Night
7 Nights - US $1,420
House
10.0(38 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $751/Night
7 Nights - US $5,256
House
10.0(38 Reviews)
4 Bedrooms
20 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $329/Night
7 Nights - US $2,306
Large Holiday Rentals and Private Villas in North Side
Over 172+ Large Holiday Rentals and Private Villas in or Near North Side
House
10.0(93 Reviews)
7 Bedrooms
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $905/Night
7 Nights - US $6,335
Apartment
10.0(2 Reviews)
5 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $799/Night
7 Nights - US $5,594
Apartment
10.0(71 Reviews)
5 Bedrooms
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,142/Night
7 Nights - US $7,992
Apartment
10.0(2 Reviews)
3 Bedrooms
20 Guests
- Private Beach
- Parking
- Ocean View
- Balcony/Terrace
US $569/Night
7 Nights - US $3,981
House
10.0(63 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,617/Night
7 Nights - US $11,316
Apartment
10.0(61 Reviews)
4 Bedrooms
20 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $315/Night
7 Nights - US $2,203
House
10.0(39 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $581/Night
7 Nights - US $4,068
Apartment
10.0(35 Reviews)
4 Bedrooms
20 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,107
House
10.0(32 Reviews)
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $672/Night
7 Nights - US $4,707
Wheelchair Accessible Holiday Homes in North Side
Over 123+ Wheelchair Accessible Holiday Homes in or Near North Side
Apartment
10.0(10 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $744/Night
7 Nights - US $5,210
Bed & Breakfast
9.5(161 Reviews)
11 Bedrooms
30 Guests
Breakfast- EV Charge Station
- Parking
- Spa
US $201/Night
7 Nights - US $1,406
Bed & Breakfast
9.4(127 Reviews)
1 Bedroom
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $309/Night
7 Nights - US $2,164
Condo
6.0(1 Review)
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $323/Night
7 Nights - US $2,263
Hotel
9.0(192 Reviews)
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $422/Night
7 Nights - US $2,954
New
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $377/Night
7 Nights - US $2,637
New
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $237/Night
7 Nights - US $1,659
Apartment
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $206/Night
7 Nights - US $1,444
Apartment
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $194/Night
7 Nights - US $1,357
North Side Private Villas and Holiday Homes Under $200
Over 434+ North Side Private Villas and Holiday Homes Under $200
Apartment
10.0(63 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $173/Night
7 Nights - US $1,214
Apartment
10.0(1 Review)
2 Bedrooms
5 Guests
- Air Conditioner
- Internet
- Child Friendly
- Security/Safety
US $90/Night
7 Nights - US $630
Apartment
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,307
House
9.8(11 Reviews)
1 Bedroom
4 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $160/Night
7 Nights - US $1,118
Apartment
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $198/Night
7 Nights - US $1,388
House
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $192/Night
7 Nights - US $1,341
House
10.0(3 Reviews)
2 Bedrooms
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,206
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $962
Instantly Bookable Holiday Homes in North Side
Over 732+ Instantly Bookable Holiday Homes in or Near North Side
Apartment
10.0(89 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,164
Apartment
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $820/Night
7 Nights - US $5,741
Apartment
10.0(81 Reviews)
3 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $212/Night
7 Nights - US $1,486
Condo
10.0(72 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $207/Night
7 Nights - US $1,452
House
10.0(68 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $451/Night
7 Nights - US $3,157
Apartment
10.0(66 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
US $231/Night
7 Nights - US $1,617
Apartment
10.0(62 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $487/Night
7 Nights - US $3,407
Condo
10.0(61 Reviews)
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $453/Night
7 Nights - US $3,173
Apartment
10.0(56 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $592/Night
7 Nights - US $4,142
Book a Last Minute Place to Stay in North Side
About Casai's Private Villas and Holiday Rentals in North Side
Discover more than 1279 vacation rentals available in North Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in North Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in North Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near North Side. On average, places to stay near North Side offer 764.34 ft², with nightly prices averaging US $456.
With Casai, finding and comparing holiday rentals in North Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the North Side, IL
There are 1279 North Side, IL Holiday Rentals
- Prices for a holiday home in North Side start at US $61
- Top rated vacation home in North Side is The Sono Chicago
- Most popular short term in North Side is Hotel Lincoln
- Cheapest place to stay in North Side is FRONTDESK Bright Open 3 BR Apt in West DePaul
- Most expensive holiday rental in North Side is Sleek New 6BR Greystone - Rooftop, In-Law Ste, Walk to Wrigley & Block to Train
Frequently Asked Questions About North Side?
What are the top holiday rentals in North Side?
With numerous options available in North Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in North Side:
- The Sono Chicago
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- ❤️ Trendy 2BR Apartment in Logan Square!
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Stylish, Inviting 2-BR near Logan Square and Wrigley Field
- Stunning Lincoln Park Single-Family House with Fantastic Game Room
- Lincoln Park Light Filled Loft
Which holiday homes in North Side are best for families?
If you're searching for a family-friendly holiday home in North Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in North Side:
How many Casai.com holiday rentals are available in North Side?
As of 2026, Casai boasts over 1279 properties listed in the North Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in North Side.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1429 |
| Near North Side Vacation Rentals in Chicago, Illinois | 592 |
| River North Vacation Rentals in Chicago, Illinois | 356 |
| West Town Vacation Rentals in Chicago, Illinois | 319 |
| Lakeview Vacation Rentals in Chicago, Illinois | 255 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 137 |
| North Center Vacation Rentals in Chicago, Illinois | 60 |
| Irving Park Vacation Rentals in Chicago, Illinois | 60 |
| Logan Square Vacation Rentals in Chicago, Illinois | 58 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 55 |
| Lake View East Vacation Rentals in Chicago, Illinois | 53 |
| Avondale Vacation Rentals in Chicago, Illinois | 46 |
| Old Town Vacation Rentals in Chicago, Illinois | 43 |
| Uptown Vacation Rentals in Chicago, Illinois | 40 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 37 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 37 |
