Discover Your Perfect Logan Square Vacation Homes

Best Vacation Homes in Logan Square

Apartment
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like-icon10.0
Exceptional
(95 Reviews)
2 Bedrooms 1 Bath 5 Guests 850 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R5,394/Night 7 Nights - R37,763
House
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like-icon10.0
Exceptional
(1 Review)
5 Bedrooms 3 Baths 12 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
More amenities
R13,889/Night 7 Nights - R97,225
star-icons-4
House
Map-icon
1 Bedroom 1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,891/Night 7 Nights - R27,239
Apartment
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like-icon10.0
Exceptional
(52 Reviews)
2 Bedrooms 1 Bath 4 Guests 850 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R5,902/Night 7 Nights - R41,308
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Apartment
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like-icon9.7
Exceptional
(3 Reviews)
2 Bedrooms 2 Baths 6 Guests 1001.04 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R4,811/Night 7 Nights - R33,677
Apartment
Map-icon
like-icon10.0
Exceptional
(51 Reviews)
2 Bedrooms 1 Bath 4 Guests 850 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,229/Night 7 Nights - R29,609
Apartment
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like-icon10.0
Exceptional
(50 Reviews)
1 Bedroom 1 Bath 2 Guests 650 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R2,979/Night 7 Nights - R20,850
Apartment
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like-icon10.0
Exceptional
(49 Reviews)
2 Bedrooms 1 Bath 4 Guests 900 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R3,799/Night 7 Nights - R26,586

Logan Square Luxury Rentals

House
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like-icon9.8
Exceptional
(55 Reviews)
6 Bedrooms 2 Baths 16 Guests 5307 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R36,345/Night 7 Nights - R254,419
House
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like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 3 Baths 15 Guests 3200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R28,840/Night 7 Nights - R201,885
House
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like-icon9.6
Exceptional
(5 Reviews)
5 Bedrooms 4 Baths 18 Guests 4500 ft²
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
R24,571/Night 7 Nights - R171,998
House
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like-icon10.0
Exceptional
(8 Reviews)
5 Bedrooms 4 Baths 12 Guests 3000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R22,186/Night 7 Nights - R155,299
House
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like-icon9.6
Exceptional
(36 Reviews)
4 Bedrooms 3 Baths 17 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R18,905/Night 7 Nights - R132,340
Condo
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like-icon9.6
Exceptional
(24 Reviews)
7 Bedrooms 6 Baths 14 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R16,231/Night 7 Nights - R113,614
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House
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like-icon9.4
Exceptional
(15 Reviews)
4 Bedrooms 3 Baths 15 Guests 2497.23 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
R14,706/Night 7 Nights - R102,944
House
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like-icon9.8
Exceptional
(19 Reviews)
4 Bedrooms 3 Baths 10 Guests 3750 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R12,722/Night 7 Nights - R89,055

Logan Square Pet Friendly Vacation Rentals

Apartment
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
2 Bedrooms 2 Baths 6 Guests 1100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R6,573/Night 7 Nights - R46,014
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Apartment
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like-icon9.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests 850.35 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R6,427/Night 7 Nights - R44,985
Apartment
Map-icon
like-icon10.0
Exceptional
(12 Reviews)
2 Bedrooms 2 Baths 6 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R7,008/Night 7 Nights - R49,054
star-icons-3
Apartment
Map-icon
like-icon9.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests 1001.04 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,477/Night 7 Nights - R24,347
Apartment
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
2 Bedrooms 2 Baths 6 Guests 1200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R7,283/Night 7 Nights - R50,982
Apartment
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 4 Guests 900 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R6,596/Night 7 Nights - R46,161
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 3 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,147/Night 7 Nights - R22,027
Apartment
Map-icon
like-icon9.6
Exceptional
(72 Reviews)
2 Bedrooms 1 Bath 5 Guests 1000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R3,953/Night 7 Nights - R27,664

Logan Square Large Vacation Homes

Apartment
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
2 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R9,739/Night 7 Nights - R68,172
House
Map-icon
like-icon10.0
Exceptional
(10 Reviews)
4 Bedrooms 2 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R9,341/Night 7 Nights - R65,394
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
5 Bedrooms 4 Baths 20 Guests 4550 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R34,259/Night 7 Nights - R239,811
House
Map-icon
like-icon9.8
Exceptional
(12 Reviews)
7 Bedrooms 4 Baths 24 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R25,102/Night 7 Nights - R175,708
House
Map-icon
like-icon8.8
Fabulous
(6 Reviews)
3 Bedrooms 1 Bath 10 Guests 1350 ft²
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
R9,737/Night 7 Nights - R68,156
Apartment
Map-icon
like-icon8.0
Excellent
(10 Reviews)
3 Bedrooms 1 Bath 10 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R4,862/Night 7 Nights - R34,037
House
Map-icon
4 Bedrooms 3 Baths 10 Guests 3500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R11,447/Night 7 Nights - R80,133
Condo
Map-icon
like-icon5.0
Average
(5 Reviews)
5 Bedrooms 4 Baths 20 Guests 5600 ft²
  • Hot Tub
    Hot Tub
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R17,762/Night 7 Nights - R124,334

Why Choose Rent By Owner for your Logan 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.

Best Times to Visit Logan Square

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as certain seasons in Logan Square offer more pleasant weather and vibrant local events that make your stay even more memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area experiences warm weather perfect for exploring and enjoying outdoor activities. This is a lively time where local events and festivals attract visitors looking for an energetic atmosphere.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This season offers mild temperatures and vibrant fall foliage, making it an ideal time to immerse yourself in the region's natural beauty and cultural events without the summer crowds.

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

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and quieter streets, providing a peaceful setting to enjoy indoor cultural attractions and cozy accommodations in this destination.

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

As the region transitions from winter, fewer visitors come during this shoulder season, offering a more relaxed experience and affordable rates for your stay in the area.

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

Weekly Weather Forecast for Logan Square

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 a private outdoor patio or deck, perfect for relaxing or dining al fresco amidst the area's vibrant atmosphere.
  • Take advantage of landscaped gardens or green spaces that may be available to enhance your outdoor experience in this destination.
  • Look for properties with outdoor seating areas, ideal for unwinding after exploring the local attractions.
  • Many rentals feature convenient parking spaces for outdoor storage or easy access during your stay here.
  • Some options include shared courtyards or communal outdoor areas to connect with fellow travelers in the region.
  • If you’re into outdoor activities, check for amenities like bike racks or storage to support your adventures around the city.
  • Seek out accommodations with viewing balconies or rooftops offering scenic vistas of the neighborhood’s skyline or surrounding scenery.
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Family Activities

  • Logan Square Farmers Market: Visit this vibrant market to enjoy fresh, local produce and family-friendly activities in the heart of the neighborhood.
  • Six Corners Shopping District: Explore a variety of shops, eateries, and entertainment options perfect for a day out with the entire family.
  • Logan Theatre: Catch a family movie at this historic theatre that offers a cozy atmosphere and classic film screenings.
  • Palmer Square Park: Relax and play at this spacious park featuring playgrounds and open areas ideal for picnics and outdoor fun.
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Adult Activities

  • Visit the Logan Square Farmers Market: Experience fresh local produce and artisanal goods at this popular outdoor market, perfect for a leisurely weekend morning.
  • Explore the Chicago History Museum’s neighborhood exhibits: Dive into the rich history of the area through engaging exhibits that reveal its unique cultural evolution.
  • Enjoy craft brews at local breweries: Savor innovative beers crafted by neighborhood breweries, offering a taste of the area's vibrant brewing scene.
  • Discover eclectic art at local galleries: Browse diverse exhibitions showcasing contemporary and traditional artworks in the region's independent art spaces.

Logan Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Coffee Shops: Take advantage of the area's thriving culinary scene by sampling local restaurants and cafes that showcase Logan Square’s unique flavors.
  • Plan for Neighborhood Walks: Discover its vibrant street art, boutique shops, and green spaces on foot to fully experience the charm of this destination.
  • Visit Community Events: Check out seasonal markets, music festivals, or neighborhood gatherings to immerse yourself in the lively community atmosphere.
  • Utilize Public Transit Options: Make the most of nearby transportation services to easily access other parts of the city and explore the region’s popular attractions.

Transportation Options

  • Chicago Transit Authority (CTA) trains and buses: You can easily access this reliable public transportation network to explore the region from your vacation rental nearby.
  • Lime and Bird e-scooters: These convenient scooters are perfect for quick trips around the neighborhood or short distances in the area.
  • Divvy bike share system: Rent a bike through Divvy to enjoy an eco-friendly and flexible way to see the city at your own pace.
  • Taxi and rideshare services: Professional Uber, Lyft, and taxi options are readily available for direct and comfortable transportation here.

Local Customs Options

  • Chicago-style Pizza Etiquette: When visiting local eateries, you’ll find that sharing a deep-dish pizza is a popular tradition here, reflecting the area's rich culinary heritage.
  • Neighborhood Greetings: It’s customary to exchange friendly nods or waves when strolling through the streets of this vibrant district, showcasing its welcoming community spirit.
  • Local Art Appreciation: Appreciating public murals and street art is part of the area's culture, offering a glimpse into the neighborhood's creative soul.
  • Seasonal Festival Participation: Engaging in seasonal events like summer block parties or fall festivals often involves embracing local customs and celebrating here together.

Frequently Asked Questions About Logan Square?

2. Which vacation homes in Logan Square are best for families?

If you are looking for a family-friendly vacation home in Logan 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 Logan Square:

3. How many Rentbyowner vacation rentals are available in Logan Square?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 177 in the Logan 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 Logan Square. 

4. What is the cancellation policy for vacation rentals in Logan Square, Chicago?

Cancellation policies vary by listing, so it’s important to review the specific terms on the property’s page. For detailed information, refer to the listing details or contact the property owner directly.

5. How do I know if a vacation rental in Logan Square has the amenities I need?

Each property listing includes a comprehensive amenities section. Be sure to review it carefully to ensure the rental meets your needs. You can also reach out to the host for additional questions about the amenities offered.

6. Are there any restrictions or house rules I should be aware of when booking in this area?

Yes, most listings specify house rules and restrictions, including pet policies, noise limitations, and check-in procedures. Always read these details thoroughly before confirming your reservation.

7. What is the process for checking in and checking out of vacation rentals in Logan Square?

The check-in and check-out procedures are listed in each property’s details. Many rentals offer flexible options, but it’s best to confirm the exact times and methods directly with the host prior to your stay.

8. How can I find the most suitable vacation rental in this destination for my travel dates?

To find the ideal property, use the search filters available on the website, such as dates, number of guests, and desired amenities. If needed, contact the host for further assistance to ensure the rental fits your needs.

Logan Square Top Rated Vacation Rentals

Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 4 Guests 1000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,171/Night 7 Nights - R22,190
Apartment
Map-icon
2 Bedrooms 2 Baths 4 Guests 1135 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R2,631/Night 7 Nights - R18,416
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 742 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R2,157/Night 7 Nights - R15,098
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 549 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R1,928/Night 7 Nights - R13,497
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 538 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R1,895/Night 7 Nights - R13,268
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 657 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R1,389/Night 7 Nights - R9,722
Apartment
Map-icon
1 Bedroom 1 Bath 3 Guests
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R817/Night 7 Nights - R5,719