North Side Vacation 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 vacation rentals

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (53 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 CA $166
CA $195 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $145
CA $619 total
includes taxes & fees
Nov 30 - Dec 1
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 CA $86
CA $274 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $255
CA $916 total
includes taxes & fees
Nov 16 - Nov 17
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.
The price is CA $140
CA $333 total
includes taxes & fees
Nov 16 - Nov 17
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.
The price is CA $98
CA $311 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $124
CA $348 total
includes taxes & fees
Nov 23 - Nov 24
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 CA $136
CA $303 total
includes taxes & fees
Nov 16 - Nov 17
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
The price is CA $116
CA $301 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $216
CA $481 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $103
CA $423 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $108
CA $269 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $170
CA $422 total
includes taxes & fees
Nov 23 - Nov 24
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 CA $96
CA $292 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $371
CA $803 total
includes taxes & fees
Nov 18 - Nov 19
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 CA $142
CA $638 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $173
CA $378 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 3BR Gem in North Center

18. 3BR Apt - Prime & Spacious

3BR Apt - Prime & Spacious
Avondale
The price is CA $116
CA $301 total
includes taxes & fees
Nov 16 - Nov 17
3BR Apt - Prime & Spacious

19. Modern 2BR with Reliable Wi-Fi

Modern 2BR with Reliable Wi-Fi
Lakeview
The price is CA $143
CA $313 total
includes taxes & fees
Nov 16 - Nov 17
Modern 2BR with Reliable Wi-Fi

20. Prime Location! 2BR Near Wrigley

Prime Location! 2BR Near Wrigley
Lakeview
The price is CA $116
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
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 vacation rentals that suit your style

Top North Side Hotel Reviews

Find out more about North Side

Everything you need to know about North Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Side vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Side vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Side vacation rentals we have selected for you start as low as CA $166 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 vacation 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 vacation.

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