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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for North Side holiday rentals

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 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 NZ$247
includes taxes & fees
18 Nov - 19 Nov
Wrigleyville Suites

2. 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 NZ$782
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking

3. 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 NZ$347
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5

4. Wrigley Field MVP Suite 1 Bedroom Apartment

Wrigley Field MVP Suite 1 Bedroom Apartment
Lakeview
9.6 out of 10, Exceptional, (14 reviews)
"Great location. 30 steps to Wrigley field. Clean. Safe. Very clean apt."
United States
Curt M.
The price is NZ$1,150
includes taxes & fees
15 Nov - 16 Nov
Wrigley Field MVP Suite 1 Bedroom Apartment

5. Fully Set Up 3BR w/ Big Kitchen

Fully Set Up 3BR w/ Big Kitchen
Lakeview
10.0 out of 10, Exceptional, (1 review)
"We were in town for my son's procedure. It was a list minute decision for us to come up the day prior to and stay. This spot was such a life saver!! And accommodating for last minute reservations! The place was beautiful! Wonderful spot! The kids even enjoyed the coding to retrieve the key!! Great communication the entire time!! Highly recommend this beautiful spot!!!"
United States
Heather L.
Fully Set Up 3BR w/ Big Kitchen

6. 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.
1BR Fully Equipped & Central

7. 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 NZ$429
includes taxes & fees
23 Nov - 24 Nov
1BR Well-Equipped Apartment

8. 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 NZ$402
includes taxes & fees
15 Nov - 16 Nov
Beautifully Set Up 2BR Space

9. 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
Comfortable 3BR/2BA Haven | Ideal for Families

10. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.8 out of 10, Exceptional, (124 reviews)
"Great place. We would stay here again."
United States
Edward S.
The price is NZ$604
includes taxes & fees
19 Nov - 20 Nov
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

11. Chic & Fully Furnished 2BR Apartment

Chic & Fully Furnished 2BR Apartment
Avondale
9.0 out of 10, Wonderful, (2 reviews)
"Excellent communication with the host and comfortable beds."
United States
Jamila D.
The price is NZ$564
includes taxes & fees
16 Nov - 17 Nov
Chic & Fully Furnished 2BR Apartment

12. 2BR Steps from Wrigley Field

2BR Steps from Wrigley Field
Lakeview
10.0 out of 10, Exceptional, (1 review)
"Great location. Clean, spacious apartment right in Wrigleyville"
United States
Daniel O.
The price is NZ$471
includes taxes & fees
15 Dec - 16 Dec
2BR Steps from Wrigley Field

13. 5 Minutes to Wrigley + Sauna + Games + Free Garage Parking

5 Minutes to Wrigley + Sauna + Games + Free Garage Parking
Lakeview
9.0 out of 10, Wonderful, (4 reviews)
"Great location, great communication, and comfortable."
United States
Doug
The price is NZ$526
includes taxes & fees
23 Nov - 24 Nov
5 Minutes to Wrigley + Sauna + Games + Free Garage Parking

14. 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 NZ$382
includes taxes & fees
14 Dec - 15 Dec
Chic & Fully Furnished Urban Studio Apartment

15. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
The price is NZ$1,004
includes taxes & fees
15 Nov - 16 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

16. Expertly designed 2BR Art Deco sanctuary.

Expertly designed 2BR Art Deco sanctuary.
Lakeview
9.4 out of 10, Exceptional, (21 reviews)
"Great place! Highly recommended!"
United States
Keith N.
The price is NZ$789
includes taxes & fees
16 Nov - 17 Nov
Expertly designed 2BR Art Deco sanctuary.

17. Cozy 3BR Gem in North Center

Cozy 3BR Gem in North Center
North Center
9.2 out of 10, Wonderful, (26 reviews)
"Host was very responsive and helpful with all questions we had."
United States
Tucker W.
The price is NZ$473
includes taxes & fees
17 Nov - 18 Nov
Cozy 3BR Gem in North Center

18. 3BR Apt - Prime & Spacious

3BR Apt - Prime & Spacious
Avondale
The price is NZ$567
includes taxes & fees
15 Dec - 16 Dec
3BR Apt - Prime & Spacious

19. Modern 2BR with Reliable Wi-Fi

Modern 2BR with Reliable Wi-Fi
Lakeview
Modern 2BR with Reliable Wi-Fi

20. Prime Location! 2BR Near Wrigley

Prime Location! 2BR Near Wrigley
Lakeview
The price is NZ$369
includes taxes & fees
15 Nov - 16 Nov
Prime Location! 2BR Near Wrigley
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.

Find holiday rentals that suit your style

Top North Side Hotel Reviews

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 favorite 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 depends 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 NZ$246 per night. Entering your travel dates in the search wizard you might find 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