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North Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for North Side vacation rentals

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
$164 nightly
The price is $192
Nov 10 - Nov 11
Total with taxes and fees
Wrigleyville Suites
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.
$166 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

3. 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
$407 nightly
The price is $416
Nov 11 - Nov 12
Total with taxes and fees
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.

4. 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.
$192 nightly
The price is $205
Nov 8 - Nov 9
Total with taxes and fees
1BR Well-Equipped Apartment
A living room with a sofa, a coffee table, a chair, a radiator, and a painting on the wall.

5. 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.
$201 nightly
The price is $215
Nov 9 - Nov 10
Total with taxes and fees
1BR Fully Equipped & Central
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
$183 nightly
The price is $203
Nov 10 - Nov 11
Total with taxes and fees
Fun Logan Sq Apt - PacMan - Sleeps 5 Pet Friendly
A living room with a sofa, a coffee table, a television displaying the Hulu logo, a plant, and a cactus on a side table.

7. 1BR Unit w/ 2 Comfy Beds

1BR Unit w/ 2 Comfy Beds
Lakeview
10.0 out of 10, Exceptional, (1 review)
$201 nightly
The price is $215
Nov 9 - Nov 10
Total with taxes and fees
1BR Unit w/ 2 Comfy Beds
A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a dining table with chairs.

8. Cozy & Modern Getaway 1BR Apt

Cozy & Modern Getaway 1BR Apt
Lakeview
$196 nightly
The price is $209
Nov 9 - Nov 10
Total with taxes and fees
Cozy & Modern Getaway 1BR Apt
A neatly made bed with a black throw blanket, a bedside lamp, and a framed abstract artwork on the wall.

9. 3BR Apt - Prime & Spacious

3BR Apt - Prime & Spacious
Avondale
$212 nightly
The price is $232
Nov 10 - Nov 11
Total with taxes and fees
3BR Apt - Prime & Spacious
A kitchen with a stainless steel range hood, a microwave, a gas stove, and an oven.

10. Vibrant 1BR Apartment in Ideal Location

Vibrant 1BR Apartment in Ideal Location
Lakeview
$195 nightly
The price is $208
Nov 8 - Nov 9
Total with taxes and fees
Vibrant 1BR Apartment in Ideal Location
A compact kitchen with a gas stove, wooden cabinets, a sink, and a door with blinds.

11. Relaxing 1BR | King Bed & Homey Feel

Relaxing 1BR | King Bed & Homey Feel
Lakeview
$199 nightly
The price is $213
Nov 9 - Nov 10
Total with taxes and fees
Relaxing 1BR | King Bed & Homey Feel
A neatly made bed with white linens, a patterned pillow, and folded towels.

12. 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.
$191 nightly
The price is $206
Nov 11 - Nov 12
Total with taxes and fees
Lush Studio Apartment
A modern bedroom with a large bed, bedside tables, a window with blinds, and two wall-mounted artworks.

13. 1BR Modern Apartment near City Center

1BR Modern Apartment near City Center
Lakeview
$215 nightly
The price is $232
Nov 16 - Nov 17
Total with taxes and fees
1BR Modern Apartment near City Center
A neatly made bed with a black frame, white bedding, and two black pillows. There is a bedside table with a lamp and a folded towel. A large mirror is on the wall to the right.

14. 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.
$183 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
2BR Steps from Wrigley Field
Interior

15. 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
$191 nightly
The price is $206
Nov 11 - Nov 12
Total with taxes and fees
Chic & Fully Furnished Urban Studio Apartment
A modern kitchen with a stainless steel stove, white cabinets, a microwave, and a dishwasher.

16. Ideal 1-Bedroom Stay

Ideal 1-Bedroom Stay
Lakeview
$212 nightly
The price is $228
Nov 29 - Nov 30
Total with taxes and fees
Ideal 1-Bedroom Stay
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.

17. 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.
$223 nightly
The price is $247
Nov 16 - Nov 17
Total with taxes and fees
Beautifully Set Up 2BR Space
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a sink, and a stove.

18. Chic & Fully Furnished 2BR Apartment

Chic & Fully Furnished 2BR Apartment
Avondale
$286 nightly
The price is $304
Nov 11 - Nov 12
Total with taxes and fees
Chic & Fully Furnished 2BR Apartment
Living area

19. Avodale 2BR Apartment | Near Logan Square

Avodale 2BR Apartment | Near Logan Square
Avondale
$163 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
Avodale 2BR Apartment | Near Logan Square
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.

20. Stylish 1BR Apt in Lakeview

Stylish 1BR Apt in Lakeview
Lakeview
$190 nightly
The price is $202
Nov 9 - Nov 10
Total with taxes and fees
Stylish 1BR Apt in Lakeview
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

The Den Hotel

The Den Hotel

10/10 Excellent
"Love staying here"
Kassandra 1-night trip
Posted 20 hours ago
The Den Hotel

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 $192 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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