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

North Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for North Side vacation rentals

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

1. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$206 nightly
The price is $212
Oct 13 - Oct 14
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a blue sofa, a patterned rug, and a television.

2. 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.
$193 nightly
The price is $217
Oct 13 - Oct 14
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A bedroom with a large bed, a bedside table, a nightstand, a window with blinds, and a wall-mounted artwork.

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

Comfortable 3BR/2BA Haven | Ideal for Families
Avondale
9.4 out of 10, Exceptional, (15 reviews)
"Great neighborhood - excellent communication - large space for family."
United States
Marc
$231 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
Comfortable 3BR/2BA Haven | Ideal for Families
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

4. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (33 reviews)
"This place was perfect for our quick weekend getaway!"
United States
Kate P.
$886 nightly
The price is $1,093
Oct 12 - Oct 13
Total with taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

5. Expertly designed 2BR Art Deco sanctuary.

Expertly designed 2BR Art Deco sanctuary.
Lakeview
9.4 out of 10, Exceptional, (18 reviews)
"Great place! Highly recommended!"
United States
Keith N.
$385 nightly
The price is $465
Oct 28 - Oct 29
Total with taxes and fees
Expertly designed 2BR Art Deco sanctuary.
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
$165 nightly
The price is $194
Nov 3 - Nov 4
Total with taxes and fees
Wrigleyville Suites
Living area

7. 5 Minutes to Wrigley + Sauna + Games + Free Garage Parking

5 Minutes to Wrigley + Sauna + Games + Free Garage Parking
Lakeview
8.8 out of 10, Excellent, (3 reviews)
"This property was a basement apartment. It was very small and had a musty odor especially in the bathroom. The bedrooms were small as well and did not have adequate room to get in and out of the bed. The kitchen was fine but lacked some essentials like hand towels. There was a lot of things that needed attention (spackle on walls that had to be painted, switch plate covers not fitting properly, unsafe entry way from patio, front gate very difficult to open). Our last day the smoke alarm which...
United States
Joy K.
$297 nightly
The price is $333
Oct 21 - Oct 22
Total with taxes and fees
5 Minutes to Wrigley + Sauna + Games + Free Garage Parking
A room with a brown leather sofa, a glass coffee table, and a bed in the background.

8. Cozy 3BR Gem in North Center

Cozy 3BR Gem in North Center
North Center
9.2 out of 10, Wonderful, (26 reviews)
"Great property for the price."
United States
Matthew R.
$289 nightly
The price is $324
Oct 27 - Oct 28
Total with taxes and fees
Cozy 3BR Gem in North Center
A courtyard with a garden, stone building, and wooden house.

9. 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
9.6 out of 10, Exceptional, (109 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
$278 nightly
The price is $343
Oct 12 - Oct 13
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
A kitchen with white cabinets, a gas stove, a coffee maker, and a toaster.

10. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (11 reviews)
"Clean"
United States
Annette
$259 nightly
The price is $285
Nov 2 - Nov 3
Total with taxes and fees
1BR Well-Equipped Apartment
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

11. Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (28 reviews)
"Location cannot be beat! So close to Wrigley and so fun! "
United States
Celia A
$880 nightly
The price is $1,086
Oct 11 - Oct 12
Total with taxes and fees
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
A modern kitchen with stainless steel appliances, wooden cabinets, and a green tiled backsplash.

12. 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.
$544 nightly
The price is $671
Oct 12 - Oct 13
Total with taxes and fees
Wrigley Field MVP Suite 1 Bedroom Apartment
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

13. 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)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
$761 nightly
The price is $939
Oct 12 - Oct 13
Total with taxes and fees
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

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

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
$823 nightly
The price is $1,016
Oct 12 - Oct 13
Total with taxes and fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A cozy living room with a sofa, a coffee table, and potted plants.

15. Large 3BR /2BA Duplex• King • Parking

Large 3BR /2BA Duplex• King • Parking
Avondale
10.0 out of 10, Exceptional, (8 reviews)
"It was a great space for a ladies reunion."
United States
Kara B.
$710 nightly
The price is $891
Oct 13 - Oct 14
Total with taxes and fees
Large 3BR /2BA Duplex• King • Parking
A living room with a fireplace, a sofa, a television, and a large window with a view of parked cars.

16. Premier 3BR Art Deco retreat with garage.

Premier 3BR Art Deco retreat with garage.
Lakeview
10.0 out of 10, Exceptional, (10 reviews)
"Great spot, location, host and accommodation."
United States
Adam L.
$612 nightly
The price is $747
Nov 3 - Nov 4
Total with taxes and fees
Premier 3BR Art Deco retreat with garage.
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

17. 5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly

5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
Lakeview
9.6 out of 10, Exceptional, (11 reviews)
"Great location. Nice big unit. Very good place for a group. Beds were comfortable Kitchen was big Parking in garage was good. Lots of stuff to walk too… Great transit location."
United States
Jason D.
$540 nightly
The price is $606
Oct 23 - Oct 24
Total with taxes and fees
5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
A kitchen with wooden cabinets, a stainless steel stove, a microwave, and a tiled backsplash.

18. 2BR on N Halsted St: Lakeview Living

2BR on N Halsted St: Lakeview Living
Lakeview
8.4 out of 10, Very good, (27 reviews)
"Great location with an easy walk to Wrigley."
United States
Jedd C.
$279 nightly
The price is $314
Nov 3 - Nov 4
Total with taxes and fees
2BR on N Halsted St: Lakeview Living
A neatly made bed with white linens, a patterned pillow, and folded towels.

19. 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.
$224 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
Lush Studio Apartment
Private kitchen

20. Chic & Fully Furnished Urban Studio Apartment

Chic & Fully Furnished Urban Studio Apartment
Lakeview
$248 nightly
The price is $274
Oct 27 - Oct 28
Total with taxes and fees
Chic & Fully Furnished Urban Studio Apartment
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

Ray's Bucktown B&B

Ray's Bucktown B&B

8/10 Good
"The best part by far was the breakfast. Food was amazing, better than any restaurant, and they had options for dietary restrictions as well. Cleanliness was average. The bathroom we had was dimly lit and the mattress had a noticeable sag to it. The place has a lot of amenities, parking for larger vehicles is street only. Not great for booking last minute. The phone number is not answered, there’s no one on-site, and communication is via text and having to upload documents. Had to set this up once we arrived, and sat outside for a while before being able to get it. Booking ahead of time, I’m sure the experience is better. There were also political activism signs hung up inside which I could do without while on vacation. Staff were friendly and helpful."
Ryan 1-night trip
Posted 2 hours ago
Ray's Bucktown B&B

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit North Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $194 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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