North Side Holiday Rentals

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Holiday Rentals in North Side

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is AU$247
includes taxes & fees
1 Sept - 2 Sept
Wrigleyville Suites

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (12)
The price is AU$339
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR in Vibrant Lakeview

Clean & Equipped 1BR Apt

8.6 out of 10, Excellent, (16)
"Good experience. Would stay there again "
The price is AU$313
includes taxes & fees
1 Sept - 2 Sept
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (17)
"Great place! 15 min walk to Wrigley "
The price is AU$304
includes taxes & fees
1 Oct - 2 Oct
Cozy, Fully Set-Up 1BR Space

Stylish 1BR in Lakeview Chicago

8.6 out of 10, Excellent, (12)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is AU$313
includes taxes & fees
1 Oct - 2 Oct
Stylish 1BR in Lakeview Chicago

Lakeview 2BR Apartment

9.2 out of 10, Wonderful, (12)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is AU$336
includes taxes & fees
2 Sept - 3 Sept
Lakeview 2BR Apartment

Sleek Style 3BR Haven - Free Parking

9.6 out of 10, Exceptional, (9)
"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 AU$511
includes taxes & fees
30 Sept - 1 Oct
Sleek Style 3BR Haven - Free Parking

Bright & Modern Lakeview Studio

9.0 out of 10, Wonderful, (2)
"Host communicated great and check in and check out was easy"
The price is AU$306
includes taxes & fees
1 Oct - 2 Oct
Bright & Modern Lakeview Studio

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (33)
"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 AU$707
includes taxes & fees
2 Sept - 3 Sept
Chic Urban Retreat Near Wrigley Field w/Parking

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is AU$511
includes taxes & fees
2 Sept - 3 Sept
2-bedroom apartment just 2 minutes drive to Wrigley Field

Beautifully Set Up 2BR Space

9.8 out of 10, Exceptional, (6)
"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 AU$339
includes taxes & fees
1 Sept - 2 Sept
Beautifully Set Up 2BR Space

2BR Stylishly Apt in Lakeview

10.0 out of 10, Exceptional, (2)
"Stayed overnight for a Cubs game, and it was a great time! Very clean, tons of space, and excellent communication with the owner. Would highly recommend!"
The price is AU$339
includes taxes & fees
2 Sept - 3 Sept
2BR Stylishly Apt in Lakeview

Bright & Spacious Lincoln Park Gem – Sleeps 9!

Bright & Spacious Lincoln Park Gem – Sleeps 9!

2BR Steps from Wrigley Field

10.0 out of 10, Exceptional, (3)
"Loved this place. Beautiful neighborhood and walking distance to great restaurants. I will book this again the next time I come to Chicago. Owners were really easy to work with. "
2BR Steps from Wrigley Field

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.6 out of 10, Exceptional, (42)
"It was a great place to stay and very spacious!"
The price is AU$1,155
includes taxes & fees
18 Sept - 19 Sept
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.6 out of 10, Exceptional, (37)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
3BR Modern Condo near Wrigley/Dwtn +Free Parking

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (34)
"Great stay"
Charming Wrigleyville Home Close to the Cubs!

Spacious 3BR | 2BA Family-Friendly Home

10.0 out of 10, Exceptional, (5)
The price is AU$351
includes taxes & fees
2 Sept - 3 Sept
Spacious 3BR | 2BA Family-Friendly Home

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (53)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK
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.
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Top North Side Hotel Reviews

Find out more about North Side

Find out more about North Side

Everything you need to know about North Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the North Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

North Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Side holiday rentals we have selected for you start as low as AU$247 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on North Side rentals

At Expedia, we put the best North Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top North Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.