North Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in North Side

Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is ￥10,595
￥19,797 total
includes taxes & fees
Oct 5 - Oct 6
Wrigleyville Suites
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (25)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
The price is ￥11,481
￥27,385 total
includes taxes & fees
Nov 3 - Nov 4
Clean & Equipped 1BR Apt
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
The price is ￥12,953
￥31,316 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR in Vibrant Lakeview
Bright & Modern Lakeview Studio
WiFi, bed sheets

Bright & Modern Lakeview Studio

9.6 out of 10, Exceptional, (8)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is ￥13,247
￥28,166 total
includes taxes & fees
Nov 3 - Nov 4
Bright & Modern Lakeview Studio
Stylish 1BR in Lakeview Chicago
Fridge, microwave, oven, stovetop

Stylish 1BR in Lakeview Chicago

8.8 out of 10, Excellent, (18)
"Terrific overall stay. Great location and nice place. Highly recommend."
The price is ￥13,247
￥29,454 total
includes taxes & fees
Nov 3 - Nov 4
Stylish 1BR in Lakeview Chicago
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (16)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is ￥13,247
￥31,662 total
includes taxes & fees
Oct 28 - Oct 29
Lakeview 2BR Apartment
Sleek Style 3BR Haven - Free Parking
3 bedrooms, iron/ironing board, travel crib, WiFi

Sleek Style 3BR Haven - Free Parking

9.6 out of 10, Exceptional, (15)
"Lived our stay here. 3 big bedrooms, clean environment. Close to things we wanted to visit. We will stay here again for sure!"
The price is ￥15,161
￥42,341 total
includes taxes & fees
Oct 6 - Oct 7
Sleek Style 3BR Haven - Free Parking
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (108)
"This was a great house, location, host....made our weekend easy and enjoyable!!"
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Boystown Chic 2BR Escape
2 bedrooms, iron/ironing board, travel crib, WiFi

Boystown Chic 2BR Escape

10.0 out of 10, Exceptional, (8)
The price is ￥13,836
￥32,715 total
includes taxes & fees
Nov 3 - Nov 4
Boystown Chic 2BR Escape
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (43)
"Great place to stay when you’re in town for the Cubbies! "
The price is ￥21,063
￥49,600 total
includes taxes & fees
Oct 15 - Oct 16
2-bedroom apartment just 2 minutes drive to Wrigley Field
Wrigley Field/Lakeview -Entire Home- Large Groups!
Property grounds

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (84)
"We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!"
Wrigley Field/Lakeview -Entire Home- Large Groups!
Walk to Wrigley Field/Monthly Discounts Available
Fridge, microwave, oven, stovetop

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (160)
"Great property and location! Host very good at responding and was extremely helpful!"
Walk to Wrigley Field/Monthly Discounts Available
Charming Wrigleyville Home Close to the Cubs!
Exterior detail

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (36)
"Great stay"
Charming Wrigleyville Home Close to the Cubs!
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
3 bedrooms, WiFi, bed sheets

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

8.8 out of 10, Excellent, (102)
"This property location is perfect. Exactly as advertised. It is on a quiet street right around the corner from Wrigley Field. It was perfect for my husband and I and our two kids with my parents. We would for sure stay here again!! "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Beautifully Set Up 2BR Space
Fridge, microwave, oven, stovetop

Beautifully Set Up 2BR Space

9.8 out of 10, Exceptional, (9)
"Great apartment, plenty of room for 4 after a Cubs game, right by Wrigley. Would definitely stay here again for a ballgame."
The price is ￥12,953
￥31,316 total
includes taxes & fees
Oct 6 - Oct 7
Beautifully Set Up 2BR Space
Cozy, Fully Set-Up 1BR Space
Fridge, microwave, oven, stovetop

Cozy, Fully Set-Up 1BR Space

9.2 out of 10, Wonderful, (24)
"We are very happy with our stay! Big comfy bed with good bed lining, a proper kitchen, a spacious bathroom, and everything was clean and nice. This place has everything you need! And communication with the host was excellent. Truly highly recommend!"
The price is ￥11,481
￥27,385 total
includes taxes & fees
Nov 3 - Nov 4
Cozy, Fully Set-Up 1BR Space
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Fridge, microwave, oven, stovetop

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

8.8 out of 10, Excellent, (42)
"The location of this property could not be beat for us while we were visiting family. We would definitely stay again!"
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Chic Urban Retreat Near Wrigley Field w/Parking
Exterior detail

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (37)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
The price is ￥22,079
￥66,111 total
includes taxes & fees
Oct 5 - Oct 6
Chic Urban Retreat Near Wrigley Field w/Parking
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (116)
"Great location within walking distance to Wrigley Field and countless restaurants. "
Stunning 3 BR in prime Chicago location
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Beach nearby

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

9.8 out of 10, Exceptional, (177)
"The house was spacious and perfect for our large group. "
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top North Side Hotel Reviews

The Villa Toscana

The Villa Toscana

10/10 Excellent
"Beautiful property, very convenient location. Love the neighborhood. "
William 3-night trip
Posted 3 days ago
The Villa Toscana

Find out more about North Side

Find out more about North Side

Search for holiday rentals in North Side on Expedia! You can easily find your home rentals, villas, holiday apartments in North Side using one of the methods below:

  • View our selection of featured holiday rentals in North Side
  • Use the map to find apartments and other holiday homes in the North Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in North Side while they last

Look no further and take a look at our great range of rental properties in North Side!