Discover Your Perfect Armour Square Vacation Homes

Best Vacation Homes in Armour Square

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8.8 (46 Reviews)
House
Mccormick Place Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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Armour Square Pet Friendly Vacation Rentals

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9.6 (227 Reviews)
Apartment
The Neighborhood Hotel-Little Italy
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
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Why Choose Rent By Owner for your Armour Square 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.

Popular Areas for Armour Square Vacation Rentals

Where are the best neighborhoods to stay in Armour Square?

Choosing the right neighborhood to stay in when visiting Armour Square, Chicago, Illinois, can greatly enhance your travel experience. This vibrant area offers convenient access to local attractions and is well-connected to the city’s main highlights. Whether you're seeking a lively atmosphere or a quieter retreat, the neighborhoods surrounding Armour Square provide diverse options for comfortable and trustworthy vacation rentals. By selecting a property in this region, you'll enjoy the convenience of exploring Chicago from a central location that combines accessibility with authentic local charm.

Chinatown

This vibrant neighborhood offers an authentic cultural experience, making it a great choice for exploring the diverse flavors and traditions of Chicago’s Chinatown while staying close to the city’s main attractions.

View 2948+ Rentals in Chinatown

Bridgeport

Known for its rich history and working-class roots, Bridgeport provides convenient access to sports venues and local dining, ideal for travelers seeking an immersive and authentic Chicago experience.

View 1421+ Rentals in Bridgeport

Douglas

Situated near major transportation routes, Douglas is perfect for those who want easy connectivity to explore the wider region while enjoying a neighborhood with a charming local feel.

View 47+ Rentals in Douglas

Dearborn Homes

Offering affordable options in a lively community setting, Dearborn Homes serves as a practical base for visitors who wish to experience the local culture and access nearby amenities.

View 1673+ Rentals in Dearborn Homes

Ickes Prairie Homes

This residential area provides a peaceful atmosphere, making it suitable for travelers looking for comfortable stays within reach of Chicago’s city sights.

View 1999+ Rentals in Ickes Prairie Homes

Best Times to Visit Armour Square

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience and ensure you enjoy the best weather and local events, making your stay in this vibrant area even more memorable.

Peak Season Highlights

summer
Summer (June to August)

During the warmest months, you can enjoy vibrant local events and sporting activities that attract visitors to this part of Chicago. Expect higher prices and increased demand for vacation rentals as travelers flock here for the lively atmosphere.

Average Temperature Daytime: around 80°F - Nighttime: around 65°F
autumn
Fall (September to November)

This season offers mild weather and colorful foliage, drawing visitors who want to experience the region's scenic beauty. Accommodation rates tend to be higher during this popular time for sightseeing and outdoor activities.

Average Temperature Daytime: around 70°F - Nighttime: around 50°F

Off-Season Highlights

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Winter (December to February)

The colder months see fewer tourists, making it a good time to find more affordable vacation rentals. You can enjoy a quieter atmosphere while exploring the region’s indoor attractions and local culture.

Average Temperature Daytime: around 35°F - Nighttime: around 25°F
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Spring (March to May)

As the weather begins to warm up, visitors start returning, but prices remain moderate. This period offers a pleasant balance of mild temperatures and fewer crowds for your stay in this area.

Average Temperature Daytime: around 55°F - Nighttime: around 40°F

Weekly Weather Forecast for Armour Square

How to Book Your Armour Square Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

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.

Explore and book the perfect rental in Armour Square

More Top-Rated Vacation Rentals in Armour Square Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 garden area for relaxing and socializing.
  • Take advantage of on-site parking facilities to conveniently explore the neighborhood and beyond.
  • Make use of outdoor grilling amenities for delicious meals while enjoying the fresh air.
  • Benefit from nearby parks and green spaces ideal for outdoor activities and leisurely walks.
  • Access bike rentals or storage options to explore the local area actively.
  • Utilize scenic views or rooftop decks that showcase the vibrant surroundings.
  • Stay close to well-maintained walking paths perfect for morning jogs or evening strolls in this destination’s outdoor setting.

Top Attractions Around Armour Square

What attractions are nearby?

In this vibrant area, you can enjoy a variety of activities nearby, from exploring local parks and sporting events to discovering cultural and culinary experiences that showcase the best of the region.

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Family Activities

  • Harrison Park: You can enjoy outdoor activities and sports in this scenic park, perfect for family picnics and casual strolls.
  • Chinatown Plaza: Explore cultural sights and indulge in authentic Asian cuisine that offers a fun and educational experience for all ages.
  • Ping Tom Memorial Park: Relax by the riverfront, where your family can engage in fishing, playground visits, or simply unwind amidst nature.
  • US Cellular Field Tours: Take a guided tour of the nearby stadium to experience Chicago’s vibrant sports culture firsthand with your loved ones.
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Adult Activities

  • Visit Guaranteed Rate Field: Enjoy the thrill of a Chicago White Sox game right in the heart of this neighborhood, offering an authentic sports experience.
  • Explore the Chinatown Historic District: Discover unique cultural attractions, dine at authentic restaurants, and immerse yourself in the vibrant Asian community for a memorable day out.
  • Relax at Ping Tom Memorial Park: Unwind by the Chicago River with scenic views, walking paths, and cultural events that showcase the area's diverse heritage.
  • Experience local cuisine: Savor a variety of delicious dishes from traditional Chinese eateries and other regional specialties within the neighborhood's culinary scene.

Other Places to Stay in Armour Square, IL

Guaranteed Rate Field
Guaranteed Rate Field Vacation Rentals
More Places to Stay Near Armour Square

Armour Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area's renowned eateries to enjoy authentic regional cuisine during your stay.
  • Utilize Public Transportation: Make commuting easier by leveraging nearby transit options to explore Chicago's attractions efficiently.
  • Engage with Community Events: Check out local happenings in the neighborhood to immerse yourself in the vibrant culture of the region.
  • Plan Outdoor Activities: Take advantage of nearby parks and recreational spaces to experience the natural beauty of here while staying active.

Transportation Options

  • Chicago Transit Authority (CTA) Trains: The CTA provides efficient train services that connect the area to downtown Chicago and beyond, making it easy for you to explore the city from your vacation rental.
  • Bus Services: Local bus routes offer convenient transportation within the neighborhood and to nearby attractions, ideal for quick trips around the region.
  • Divvy Bike Sharing: You can rent bikes through Divvy to enjoy a flexible and environmentally friendly way to navigate here at your own pace.
  • Taxis and Ride-Sharing Services: Taxis and popular ride-share options like Uber and Lyft provide door-to-door service, offering comfort and convenience during your stay.

Local Customs Options

  • Community Sports Traditions: Participating in local sports events and supporting the Chicago White Sox at Guaranteed Rate Field are cherished customs here that reflect the area's passionate sports culture.
  • Food and Beverage Etiquette: Sharing hearty, family-style meals featuring Chicago-style hot dogs and deep-dish pizza is a common way visitors embrace the culinary traditions of this region.
  • Celebrating Local Festivals: Engaging in annual neighborhood festivals and public parades highlights the community spirit and vibrant cultural scene unique to the area.
  • Respect for Neighborhood Heritage: Respecting and preserving the historic architecture and local landmarks reflects the community's pride in its rich heritage and longstanding customs.

Frequently Asked Questions About Armour Square?

1. What are the top vacation rentals in Armour Square?

There are a lot of options in Armour Square. If you plan on staying in the Armour Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Armour Square:

2. How many vacation rentals have private pools in Armour Square?

There are 10 vacation rentals with private pools near Armour Square. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Armour Square are best for families?

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

4. How many Rentbyowner vacation rentals are available in Armour Square?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 1370 in the Armour Square 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 Armour Square. 

5. What is the cancellation policy for vacation rentals near Armour Square?

Cancellation policies vary depending on the individual listing. You should review the specific property's terms and conditions before booking or contact the host directly for clarification.

6. How do I confirm the availability of a rental in this area?

Availability is listed on each property page, but it’s best to reach out to the owner or host directly to verify current booking status and ensure your preferred dates are open.

7. Are there any fees when booking a vacation rental in Armour Square?

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the listing details. For exact amounts, review the listing carefully or contact the property owner.

8. What amenities can I expect in a typical vacation rental here?

Amenities vary by property but generally include essentials like Wi-Fi, kitchen facilities, and parking. Specific amenities are detailed on each listing, so be sure to check those before making your reservation.

9. Is it possible to request special arrangements for my stay?

Many hosts accommodate special requests, but you should communicate your needs directly with the property owner prior to booking to confirm availability and acceptance.