Photo by Scott Kleinschmidt

Wrigleyville holiday rentals

We found 400 holiday rentals — enter your dates for availability
Discover a selection of 51 apartments, 10 flats 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:1 Jan - 8 Jan

Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Bedroom 1 - King Bed
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
S$8,642
for 7 nights, 1 home
S$1,235 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Living area
Belmont Harbor
Exterior
Living area
Exceptional
(193 reviews)

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

Chicago

8% off
S$5,224
for 7 nights, 1 home
S$746 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Room
Dining
Living area
Living area
Exceptional
(7 reviews)

The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.

Chicago

7% off
S$10,052
for 7 nights, 1 apartment
S$1,436 per night
includes taxes & fees
The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.
Games room
Living area
Lobby
Games room
Exceptional
(10 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

7% off
S$8,495
for 7 nights, 1 apartment
S$1,214 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Interior
Exterior
Room
Dining
Exceptional
(37 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
S$6,970
for 7 nights, 1 apartment
S$996 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Living area
Property grounds
Private kitchen
Exterior
Exceptional
(109 reviews)

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

Chicago

14% off
S$2,263
for 7 nights, 1 apartment
S$323 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Room
Living area
Dining
Private kitchen
Exceptional
(114 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
S$7,089
for 7 nights, 1 home
S$1,013 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Private kitchen
Room
Living area
Interior
Exceptional
(63 reviews)

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

Chicago

10% off
S$4,202
for 7 nights, 1 apartment
S$600 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Interior
Interior
Room
Living area
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
S$7,702
for 7 nights, 1 home
S$1,100 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Living area
Property grounds
Outdoor dining
Exterior detail
Exceptional
(30 reviews)

2BD/1 BA with summer patio in quiet Roscoe Village

Chicago

7% off
S$1,866
for 7 nights, 1 apartment
S$267 per night
includes taxes & fees
2BD/1 BA with summer patio in quiet Roscoe Village
Living area
Interior
Private kitchen
Room
Exceptional
(22 reviews)

Chicago Bear Den

Chicago

7% off
S$2,063
for 7 nights, 1 apartment
S$295 per night
includes taxes & fees
Chicago Bear Den
Bedroom 1 (with Desk)
Side stairwell to Entrance of Unit (see red umbrella on deck)
Private Patio
Living Room
Exceptional
(39 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off
S$2,443
for 7 nights, 1 apartment
S$349 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Room
Exterior detail
Dining
Outdoor dining
Exceptional
(39 reviews)

Stylish Two Bedroom - A block from Wrigley Field

Chicago

7% off
S$3,531
for 7 nights, 1 apartment
S$504 per night
includes taxes & fees
Stylish Two Bedroom - A block from Wrigley Field
Living area
Living area
Terrace/patio
Dining
Exceptional
(58 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
S$3,806
for 7 nights, 1 apartment
S$544 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Private kitchen
Living area
Interior
Room
Wonderful
(155 reviews)

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

Chicago

7% off
S$2,769
for 7 nights, 1 apartment
S$396 per night
includes taxes & fees
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Room
Interior
Private kitchen
Interior
Wonderful
(19 reviews)

HIP EAST LAKEVIEW/LINCOLN PARK DESIGNER FLAT

Chicago

6% off
S$1,472
for 7 nights, 1 apartment
S$210 per night
includes taxes & fees
HIP EAST LAKEVIEW/LINCOLN PARK DESIGNER FLAT
Living area
Exterior detail
Dining
Interior
Exceptional
(11 reviews)

The Roscoe Village Guesthouse

Chicago

7% off
S$1,965
for 7 nights, 1 apartment
S$281 per night
includes taxes & fees
The Roscoe Village Guesthouse
Interior
Living area
Room
Outdoor dining
Exceptional
(10 reviews)

Premier 3BR Art Deco retreat with garage.

Chicago

7% off
S$7,746
for 7 nights, 1 apartment
S$1,107 per night
includes taxes & fees
Premier 3BR Art Deco retreat with garage.
Living area
Exterior
Room
Private kitchen
Wonderful
(17 reviews)

Expertly designed 2BR Art Deco sanctuary.

Chicago

7% off
S$3,492
for 7 nights, 1 apartment
S$499 per night
includes taxes & fees
Expertly designed 2BR Art Deco sanctuary.
Living area
Living area
Room
Private kitchen
Exceptional
(14 reviews)

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

Chicago

7% off
S$4,096
for 7 nights, 1 apartment
S$585 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

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    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