A nighttime city skyline reflected in a calm body of water, with illuminated buildings and a bridge.

North Side Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for North Side holiday rentals

A modern living room with a blue sofa, a patterned rug, and a television.

1. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is AU$273
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A living room with a sofa, a coffee table, a chair, a radiator, and a painting on the wall.

2. 1BR Fully Equipped & Central

1BR Fully Equipped & Central
Lakeview
10.0 out of 10, Exceptional, (1 review)
"Look to the right in the entry of building E for lockbox containing the key, not the left."
United States
Trevor F.
The price is AU$423
includes taxes & fees
19 Nov - 20 Nov
1BR Fully Equipped & Central
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (49 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is AU$251
includes taxes & fees
10 Nov - 11 Nov
Wrigleyville Suites
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

4. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is AU$612
includes taxes & fees
11 Nov - 12 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a green sofa, a coffee table, a chair, and a TV. There is a ceiling fan, a window with blinds, and a lamp on a side table.

5. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (12 reviews)
"Very good location "
United States
wendy h.
The price is AU$341
includes taxes & fees
11 Nov - 12 Nov
1BR Well-Equipped Apartment
A modern living room with a blue sofa, a flat-screen TV on a white stand, and a small trash bin.

6. Fun Logan Sq Apt - PacMan - Sleeps 5 Pet Friendly

Fun Logan Sq Apt - PacMan - Sleeps 5 Pet Friendly
Avondale
Fun Logan Sq Apt - PacMan - Sleeps 5 Pet Friendly
A neatly made bed with white linens, a patterned pillow, and folded towels.

7. Lush Studio Apartment

Lush Studio Apartment
Lakeview
8.0 out of 10, Very good, (1 review)
"It’s a great room for a very short stay. Clean and Comfortable bed and the smaller amenities were provided. The neighborhood is awesome. The Check in process requires a picture of you and a picture of your drivers license which we found excessive. The door instructions were complex and not 100% accurate but workable with some patience ."
United States
Brad B.
The price is AU$310
includes taxes & fees
11 Nov - 12 Nov
Lush Studio Apartment
Living area

8. Central 1BR Retreat Apartment

Central 1BR Retreat Apartment
Lakeview
The price is AU$331
includes taxes & fees
15 Nov - 16 Nov
Central 1BR Retreat Apartment
A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a dining table with chairs.

9. Cozy & Modern Getaway 1BR Apt

Cozy & Modern Getaway 1BR Apt
Lakeview
The price is AU$342
includes taxes & fees
15 Nov - 16 Nov
Cozy & Modern Getaway 1BR Apt
Interior

10. Chic & Fully Furnished Urban Studio Apartment

Chic & Fully Furnished Urban Studio Apartment
Lakeview
10.0 out of 10, Exceptional, (1 review)
"Free parking is veryyy limited but beautiful area"
United States
Antje
The price is AU$312
includes taxes & fees
11 Nov - 12 Nov
Chic & Fully Furnished Urban Studio Apartment
A bathroom with a toilet, sink, and mirror.

11. Vibrant 1BR Apartment in Ideal Location

Vibrant 1BR Apartment in Ideal Location
Lakeview
The price is AU$320
includes taxes & fees
15 Nov - 16 Nov
Vibrant 1BR Apartment in Ideal Location
A compact kitchen with a gas stove, wooden cabinets, a sink, and a door with blinds.

12. Relaxing 1BR | King Bed & Homey Feel

Relaxing 1BR | King Bed & Homey Feel
Lakeview
The price is AU$342
includes taxes & fees
15 Nov - 16 Nov
Relaxing 1BR | King Bed & Homey Feel
A teal sofa with a cushion that reads "THIS IS OUR happy place," flanked by two black pillows. Above the sofa, there are two abstract wall art pieces. A glass coffee table with a plant is in front of the sofa.

13. Stylish 1BR Apt in Lakeview

Stylish 1BR Apt in Lakeview
Lakeview
The price is AU$343
includes taxes & fees
16 Nov - 17 Nov
Stylish 1BR Apt in Lakeview
A modern kitchen with dark cabinetry, a microwave, a stove, and a coffee maker.

14. Comfortable 3BR/2BA Haven | Ideal for Families

Comfortable 3BR/2BA Haven | Ideal for Families
Avondale
9.6 out of 10, Exceptional, (19 reviews)
"Great neighborhood - excellent communication - large space for family."
United States
Marc
The price is AU$315
includes taxes & fees
11 Nov - 12 Nov
Comfortable 3BR/2BA Haven | Ideal for Families
A living room with a brick wall, a large abstract painting, a beige sofa, a dark sofa, a coffee table with a remote control, and a window with a view of trees.

15. Paradise 1BR Apt in Lincoln Park

Paradise 1BR Apt in Lincoln Park
Lincoln Park
4.6 out of 10, (4 reviews)
"Worst experience. My husband paid for my sister and I to have a girls night in Chicago. This host told me last-minute that they don’t accept third party payments. So we sent all the required documentation to fix it and still stay. Check in is at 3pm, I got a message at 2pm saying they had to cancel our reservation for “maintenance issues”. My sister then contacted the same host, same listing minutes after and asked if this place was available for the night and the host said yes. Needless to say...
United States
Meranda M.
The price is AU$402
includes taxes & fees
22 Nov - 23 Nov
Paradise 1BR Apt in Lincoln Park
A living room with a dark blue sofa, a small coffee table, a floor lamp, and a ceiling fan. There are two windows with blinds, a radiator, and a potted plant on the windowsill.

16. Beautifully Set Up 2BR Space

Beautifully Set Up 2BR Space
Lakeview
9.0 out of 10, Wonderful, (2 reviews)
"Approval/check-in process was a little more laborous than expected but great deal for a really nice place and location. Would stay again!"
United States
Tavia S.
The price is AU$375
includes taxes & fees
15 Nov - 16 Nov
Beautifully Set Up 2BR Space
A modern bedroom with a large bed, bedside tables, a window with blinds, and two wall-mounted artworks.

17. 1BR Modern Apartment near City Center

1BR Modern Apartment near City Center
Lakeview
The price is AU$342
includes taxes & fees
16 Nov - 17 Nov
1BR Modern Apartment near City Center
A modern bedroom with a bed, bedside table, lamp, and a grey sofa with a decorative pillow.

18. Stylish Studio near Boystown

Stylish Studio near Boystown
Lakeview
10.0 out of 10, Exceptional, (1 review)
"Very nice cozy space for a night! No complaints at all, and it was very clean. Would definitely stay again "
United States
Dave S.
The price is AU$242
includes taxes & fees
24 Nov - 25 Nov
Stylish Studio near Boystown
A kitchen with a white stove, a kettle, a coffee maker, and a knife block.

19. Prime Location! 2BR Near Wrigley

Prime Location! 2BR Near Wrigley
Lakeview
The price is AU$346
includes taxes & fees
15 Nov - 16 Nov
Prime Location! 2BR Near Wrigley
A modern kitchen with a stainless steel stove, white cabinets, a microwave, and a dishwasher.

20. Ideal 1-Bedroom Stay

Ideal 1-Bedroom Stay
Lakeview
The price is AU$344
includes taxes & fees
29 Nov - 30 Nov
Ideal 1-Bedroom Stay
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 Den Hotel

The Den Hotel

10/10 Excellent
"Room was clean area safe and Convenient"
Steven 1-night trip
Posted less than an hour ago
The Den Hotel

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$251 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. 

Explore a world of travel with Expedia