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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
8.0 out of 10, Very good, (56 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
$198 nightly
The price is $232
Sep 23 - Sep 24
Total with taxes and fees
Wrigleyville Suites
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

2. 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
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
A courtyard with a garden, stone building, and wooden house.

3. 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, (103 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
$260 nightly
The price is $321
Sep 27 - Sep 28
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
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, (65 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$226 nightly
The price is $232
Sep 28 - Sep 29
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

5. 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.
$880 nightly
The price is $1,086
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

6. 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.
$393 nightly
The price is $441
Sep 24 - Sep 25
Total with taxes and fees
5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

7. 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, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
$762 nightly
The price is $940
Oct 5 - Oct 6
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 neon sign, a fireplace, a television, and a guitar.

8. 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, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
$496 nightly
The price is $612
Sep 29 - Sep 30
Total with taxes and fees
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A room with a brown leather sofa, a glass coffee table, and a bed in the background.

9. Cozy 3BR Gem in North Center

Cozy 3BR Gem in North Center
North Center
9.2 out of 10, Wonderful, (25 reviews)
"Great property for the price."
United States
Matthew R.
$273 nightly
The price is $304
Sep 29 - Sep 30
Total with taxes and fees
Cozy 3BR Gem in North Center
A balcony with a wooden table and chairs, a potted plant, and a lattice screen.

10. 2R- ❤️ Stylish and Cozy 2BR in Logan Square!

2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (58 reviews)
"Excellent stay. Nice location"
United States
Daniel R.
$295 nightly
The price is $348
Sep 28 - Sep 29
Total with taxes and fees
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
A cozy living room with a sofa, a coffee table, and potted plants.

11. 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.
$548 nightly
The price is $687
Sep 23 - Sep 24
Total with taxes and fees
Large 3BR /2BA Duplex• King • Parking
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.
$540 nightly
The price is $666
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field MVP Suite 1 Bedroom Apartment

13. 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.
$256 nightly
The price is $287
Oct 20 - Oct 21
Total with taxes and fees
2BR on N Halsted St: Lakeview Living
A dining area with a large table, chairs, a fireplace, and a modern chandelier.

14. The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Lakeview
10.0 out of 10, Exceptional, (5 reviews)
"Great hosts that were very attentive to our requests! Loved the design and cleanliness of this place. Location was excellent. The pool table and the spacious deck were great amenities for our group during this stay."
United States
Sam E.
$827 nightly
The price is $1,008
Sep 30 - Oct 1
Total with taxes and fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
A living room with a fireplace, a sofa, a television, and a large window with a view of parked cars.

15. 3BR Art Deco retreat with garage.

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.
$658 nightly
The price is $803
Oct 5 - Oct 6
Total with taxes and fees
3BR Art Deco retreat with garage.
A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

16. Expertly designed 2BR Art Deco sanctuary.

Expertly designed 2BR Art Deco sanctuary.
Lakeview
9.2 out of 10, Wonderful, (16 reviews)
"Awesome place and steps from Wrigley!"
United States
Mark A.
$379 nightly
The price is $457
Sep 30 - Oct 1
Total with taxes and fees
Expertly designed 2BR Art Deco sanctuary.
A living room with a fireplace, a flat-screen TV mounted above it, a round coffee table, a sofa, and a window with blinds.

17. 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
$221 nightly
The price is $243
Sep 28 - Sep 29
Total with taxes and fees
Comfortable 3BR/2BA Haven | Ideal for Families
A modern living room with a flat-screen TV, a green sofa, a coffee table, a sideboard, and a ceiling fan.

18. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (11 reviews)
"Clean"
United States
Annette
$233 nightly
The price is $254
Sep 23 - Sep 24
Total with taxes and fees
1BR Well-Equipped Apartment
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

19. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
$1,701 nightly
The price is $2,074
Sep 30 - Oct 1
Total with taxes and fees
Premier 9BR Art Deco manor with garage.
A modern living room with a blue sofa, a patterned rug, and a television.

20. 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, (1 review)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
$186 nightly
The price is $209
Sep 30 - Oct 1
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
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 Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

10/10 Excellent
"PERFECT place to stay for a visit to Wrigley Field! Great atmosphere! Great location!"
Rob 3-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Wrigleyville

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 $232 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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