Discover Your Perfect Wrigleyville Vacation Homes

Wrigleyville Pet Friendly Vacation Rentals

Why Choose Rent By Owner for your Wrigleyville Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Wrigleyville

When should you plan your Vacation Rentals stay?

Timing your visit to this vibrant destination can greatly enhance your experience, so consider planning your stay during the seasons when the region's local events and climate align perfectly with your interests.

Peak Season Highlights

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Summer (June - August)

During the summer months, you can enjoy the lively atmosphere of this destination with warm weather and longer daylight hours, perfect for exploring the area’s vibrant local scene.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
autumn
Fall (September - November)

Visit during the fall when the region's scenery transforms with colorful foliage, making it an ideal time for outdoor activities and experiencing the local culture at its peak.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Winter (December - February)

In winter, the area tends to be quieter, providing a more relaxed experience with cooler temperatures that create a cozy atmosphere for those looking to avoid crowds.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Early Spring (March - April)

During early spring, the region begins to awaken from the colder months, but attractions are less crowded, offering a peaceful stay as nature starts to bloom again.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Wrigleyville

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to a private outdoor patio or balcony to relax while taking in the vibrant neighborhood views.
  • Make use of the on-site outdoor grilling area for a convenient and delicious cookout experience.
  • Take advantage of nearby parks or green spaces ideal for outdoor activities and picnics.
  • Benefit from outdoor seating areas designed for socializing and unwinding after exploring the city.
  • Find options for outdoor fitness equipment or designated workout spaces to stay active during your stay.
  • Discover patios or courtyards that provide a peaceful retreat in the lively local scene.
  • Utilize outdoor storage spaces for bicycles or other recreational gear to enhance your visit here.
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Family Activities

  • Wrigley Field Tour: Experience the historic baseball stadium nearby, where you can explore the iconic ballpark and learn about Chicago sports history.
  • Lakefront Recreation: Enjoy family-friendly activities along Lake Michigan, including picnicking, biking, and walking along the scenic lakefront paths.
  • Chicago Sports Museum: Visit this engaging museum to discover interactive exhibits celebrating Chicago’s rich sports culture, perfect for family outings.
  • Local Dining Experiences: Savor diverse culinary options at family-friendly restaurants within the neighborhood, offering something for everyone's taste buds.
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Adult Activities

  • Catch a Chicago Cubs Game at Wrigley Field: Immerse yourself in the classic American baseball experience by attending a game at this iconic stadium nestled in the heart of the area.
  • Explore the Local Bars and Breweries: Sample craft beers and enjoy lively atmospheres at the neighborhood's renowned bars that showcase the region's vibrant nightlife.
  • Visit the Wrigleyville Trolley Tour: Discover the history and key attractions of this lively neighborhood through guided trolley tours that highlight its unique charm.
  • Enjoy Live Music and Entertainment: Experience diverse live performances at local venues, offering entertainment options that cater to various musical tastes in the region.

Other Places to Stay in Wrigleyville, IL

Wrigleyville Travel Tips

How Can You Make the Most of Your Stay?

  • Visit Local Sports Venues: Make sure to catch a game or tour the iconic stadiums to experience the area's vibrant sports culture firsthand.
  • Explore Neighborhood Eateries and Bars: Take advantage of the diverse dining options and lively bars that showcase the region’s culinary scene and nightlife.
  • Plan Your Transportation in Advance: Use nearby transit options and walkable streets to easily navigate between popular spots and maximize your time here.
  • Check Out Seasonal Events: Align your stay with local festivals or outdoor activities to fully immerse yourself in the destination’s unique community spirit.

Transportation Options

  • CTA Metra Station: The nearby CTA Metra station offers convenient commuter rail options for exploring Chicago and beyond, making it easy to reach popular attractions from your vacation rental in the area.
  • Chicago Transit Authority Bus Services: Extensive bus routes serve this destination, providing accessible transportation throughout Wrigleyville and connecting you effortlessly to other parts of the city.
  • Divvy Bicycle Sharing: For an eco-friendly and flexible way to explore here, Divvy bike rentals provide a cost-effective option directly within the neighborhood.
  • taxis and Rideshare Services: Taxis and popular rideshare apps like Uber and Lyft are readily available, offering quick and reliable transportation around the region for added convenience during your stay.

Local Customs Options

  • Cheering at Wrigley Field: Locals and visitors alike celebrate their favorite teams with passionate cheers during baseball games, creating a lively sports atmosphere in the area.
  • Enjoying Craft Beers: The region boasts a rich tradition of craft beer culture, where sampling local brews is a common custom among those here to unwind and socialize.
  • Participating in Neighborhood Festivals: Community events and festivals are an integral part of life, offering a chance to experience local music, food, and traditions firsthand.
  • Respecting Historic Landmarks: Visitors are encouraged to honor the historic architecture and landmarks that define the area's unique charm and cultural heritage.

Frequently Asked Questions About Wrigleyville?

2. Which vacation homes in Wrigleyville are best for families?

If you are looking for a family-friendly vacation home in Wrigleyville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wrigleyville:

3. How many Rentbyowner vacation rentals are available in Wrigleyville?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 64 in the Wrigleyville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Wrigleyville. 

4. What is the cancellation policy for vacation rentals near Wrigleyville in Chicago?

Cancellation policies vary depending on the property owner or host. You should review the specific listing details or contact the host directly to understand the terms before booking.

5. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or taxes are typically listed on the property details page. Be sure to read the full listing or reach out to the owner for clarification.

6. How do I know if a vacation rental in Wrigleyville has the amenities I need?

All listed amenities are detailed in each property's description. If you have specific requirements, contact the host directly to confirm availability and suitability.

7. What is the process for securing my reservation in this neighborhood?

You can reserve your stay by completing the booking through the platform and following the owner's instructions. For any questions or special requests, contact the host beforehand.

8. Are there any restrictions or house rules I should be aware of before booking?

Yes, each vacation rental has its own house rules and restrictions, which are included in the listing details. Review them carefully and communicate with the owner if you have any concerns.