
Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the North Side offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Chicago
- ·
- Wrightwood Neighbors
- 0.25 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Security/Safety
-
Parking
-
Air Conditioner
-
Internet
-
Security/Safety
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Chicago
- ·
- Old Town Triangle
- 0.18 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Chicago
- ·
- Wrightwood Neighbors
- 0.25 mi to center
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Air Conditioner
-
Internet
-
Child Friendly
-
Security/Safety
-
Air Conditioner
-
Internet
-
Child Friendly
-
Security/Safety
- Chicago
- ·
- Lake View East
- 0.15 mi to center
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
- Chicago
- ·
- Lincoln Park
- 0.23 mi to center
-
Hot Tub
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Hot Tub
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Chicago
- ·
- Logan Square
- 0.48 mi to center
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Balcony/Terrace
-
Child Friendly
-
Laundry
-
Security/Safety
-
Balcony/Terrace
-
Child Friendly
-
Laundry
-
Security/Safety
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Chicago
- ·
- Logan Square
- 0.48 mi to center
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Balcony/Terrace
-
Child Friendly
-
Laundry
-
Security/Safety
-
Balcony/Terrace
-
Child Friendly
-
Laundry
-
Security/Safety
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Chicago
- ·
- Sheffield Neighbors
- 0.27 mi to center
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
-
Internet
-
Child Friendly
-
Laundry
-
Security/Safety
-
Internet
-
Child Friendly
-
Laundry
-
Security/Safety
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Chicago
- ·
- Mid-North District
- 0.17 mi to center
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
Find the Perfect Resort Vacation in the North Side
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the North Side
What are the Top Resort Locations Across the North Side?
Discover resorts in the most sought-after travel destinations nationwide:
Lakeview
Lakeview VACATION RENTALSLincoln Park
Lincoln Park VACATION RENTALSNorth Center
North Center VACATION RENTALSLogan Square
Logan Square VACATION RENTALSWrigleyville
Wrigleyville VACATION RENTALSLake View East
Lake View East VACATION RENTALSOld Town
Old Town VACATION RENTALSOld Town Triangle
Old Town Triangle VACATION RENTALSAvondale
Avondale VACATION RENTALSSheffield and DePaul
Sheffield and DePaul VACATION RENTALSWest Bucktown
West Bucktown VACATION RENTALSWrightwood Neighbors
Wrightwood Neighbors VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the North Side. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the North Side
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the North Side, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the North Side? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
Resorts Vacations FAQs
What are the top vacation rentals in North Side?
There are a lot of options in North Side. If you plan on staying in the North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in North Side:
Which vacation homes in North Side are best for families?
If you are looking for a family-friendly vacation home in North Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in North Side:
How many vacation rentals are available in North Side?
Currently, the total number of properties listed in 2026 is over 1 in the North Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in North Side.
More Resorts Vacations to Explore
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool