Photo by Scott Kleinschmidt

Wrigleyville holiday rentals

We found 350 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Wrigleyville that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Wrigleyville

Showing deals for:13 Nov - 20 Nov

Private kitchen
Living area
Terrace/patio
Living area
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
S$3,452
for 7 nights, 1 apartment
S$493 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Heritage Outpost cafe in lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Rooftop lounge leads to roof deck with 360 degree skyline views
Doorman building with grand lobby
Exceptional
(14 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago

7% off
S$2,563
for 7 nights, 1 apartment
S$366 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Exterior
Belmont Harbor
Living area
Private kitchen
Exceptional
(190 reviews)

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

Chicago

14% off
S$5,148
for 7 nights, 1 home
S$735 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private Patio
Neighborhood Photo
Interior
Private kitchen
Exceptional
(35 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off
S$1,988
for 7 nights, 1 apartment
S$284 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Living area
Interior
Living area
Living area
Exceptional
(63 reviews)

EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!

Chicago

10% off
S$4,199
for 7 nights, 1 apartment
S$600 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Private kitchen
Exterior
Dining
Room
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
S$7,839
for 7 nights, 1 apartment
S$1,120 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Living area
Property grounds
Living area
Exterior
Exceptional
(91 reviews)

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

Chicago

7% off
S$2,586
for 7 nights, 1 apartment
S$369 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Dining
Exterior detail
Outdoor dining
Interior
Exceptional
(37 reviews)

Stylish Two Bedroom - A block from Wrigley Field

Chicago

7% off
S$2,492
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
Stylish Two Bedroom - A block from Wrigley Field
Room
Interior
Bathroom
Living area
Exceptional
(20 reviews)

Chicago Bear Den

Chicago

7% off
S$2,253
for 7 nights, 1 apartment
S$322 per night
includes taxes & fees
Chicago Bear Den
Private kitchen
Living area
Room
Exterior
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
S$4,012
for 7 nights, 1 apartment
S$573 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
Room
Living area
Outdoor dining
Dining
Exceptional
(31 reviews)

The Roscoe Village Brownstone

Chicago

7% off
S$2,454
for 7 nights, 1 apartment
S$351 per night
includes taxes & fees
The Roscoe Village Brownstone
Interior
Living area
Dining
Room
Wonderful
(147 reviews)

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Chicago

7% off
S$2,811
for 7 nights, 1 apartment
S$402 per night
includes taxes & fees
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Wrigleyville?
The most in-demand types of holiday rentals in Wrigleyville are apartments. Want something different? Vrbo has numerous options to match our guests' diverse needs, so you'll see holiday homes in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — discover yours today.
How much does it cost to rent a holiday rental in Wrigleyville?
Several things can affect what you'll pay for your holiday rental in Wrigleyville, including the length of stay, season and type of property. But, all of our holiday homes have one thing in common — exceptional value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Wrigleyville?
When you travel and the style and size of the property will influence the cost of your beachside escape. Put in your Wrigleyville travel dates to see your options on Vrbo. Can't live without a private pool? Use the filters to select the features and amenities you want in your rental.
Are there pet-friendly holiday rentals in Wrigleyville?
Pack a squeezy toy and a bone for your beloved pooch because Wrigleyville has 16 holiday homes that put out the welcome mat to pets. Let your happy hound enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates and destination, then check the "Pets allowed" filter box.
What are popular rental amenities in Wrigleyville?
When it comes to rental amenities that people are looking for in Wrigleyville, a fireplace, nearby museums and a chef rank the highest. With Vrbo holiday homes, you'll have options to match your taste and style, whether you're taking a trip with friends, relatives or even pets.
Are there large group holiday rentals in Wrigleyville?
With three holiday rentals that can sleep 10 guests or more in Wrigleyville, you don't have to cross anyone off the invite list. From extended family holidays to events like Christmas or New Year's Eve parties, Vrbo will help you find a large group rental that fits the occasion.
Are there holiday rentals in Wrigleyville that welcome kids?
With 16 family-friendly holiday properties available in Wrigleyville, now is a fantastic time to introduce your kids to the pleasures of travel. Check our "Properties good for families" filter to search for stays loaded with amenities perfect for holidaying families, such as full kitchens, private pools, bunk beds and entertainment areas.
What are the top attractions for families in Wrigleyville?
Keep the kids entertained at these top family-friendly attractions in Wrigleyville:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Can I find two-bedroom holiday rentals in Wrigleyville?
Take your pick of six two-bedroom properties in Wrigleyville. Give the kids the second room or maybe fill it with a couple of your favourite people. There's enough space for whoever's fortunate enough to be coming along.
Are there holiday rentals with WiFi in Wrigleyville?
Wrigleyville has three holiday rentals with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to scrolling social media, these Vrbo homes make it a breeze to go online.
How can I find holiday rentals with air conditioning in Wrigleyville?
Wrigleyville has 15 holiday rentals where you'll be able to wind down in air-conditioned comfort. To book a property on Vrbo that offers this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Wrigleyville?
The minimum required age is usually 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your chosen Wrigleyville holiday rental before booking your stay.
How long can I rent a holiday rental in Wrigleyville for?
The amount of time you can stay in a Wrigleyville holiday rental for varies depending on the property. Simply tap in your preferred travel dates to browse available options offering longer term stays. They have the things you need to make your extended holiday more comfortable and enjoyable, such as air conditioning and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stick around for longer for less.

More holiday ideas