Logan Square holiday lettings

We found 843 holiday rentals — enter your dates for availability

Discover a selection of 17 homes, 57 apartments and other holiday rentals in Logan Square that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Why visit Logan Square

  • Cultural attractions: Discover local gems like the Logan Theatre and the scenic Logan Square Park, perfect for families and culture enthusiasts.
  • Outdoor activities: Enjoy the vibrant boulevards and numerous urban parks, ideal for leisurely strolls and outdoor adventures.
  • Local cuisine: Indulge in a variety of delightful eateries that showcase the neighbourhood's culinary diversity.
  • Lively atmosphere: Experience the energetic vibe at Emporium Logan Square, a hub for entertainment and socialising.
  • Accommodation options: Choose from a range of holiday rentals, from cosy flats to spacious apartments, tailored for your stay.

Popular types of accommodation around Logan Square

Vrbo offers a variety of vacation rentals in Logan Square, including apartments, private holiday homes, and condos. Whether you're seeking a spacious bedroom apartment in Logan or a cosy flat, you’ll find the perfect accommodation to suit your needs. With options like apartment rentals in Logan Square, your ideal getaway is just a click away. Choose the right place for your stay and enjoy all that this vibrant area has to offer.

  • Flats: The most sought-after option for holiday rentals in Logan Square is flats, offering a comfortable and convenient stay.
  • Private Holiday Homes: Coming in second, private holiday homes provide a homely atmosphere perfect for families or groups.
  • Condos: In third place, condos present modern amenities and spacious living for a relaxing getaway.
  • Cottages: Rounding out the list, cottages offer a quaint and charming retreat for a peaceful escape.**

Top attractions near Logan Square

Logan Square is an ideal destination for families and those seeking a vibrant city experience. Visitors can explore local attractions such as the Logan Theatre and Logan Square Park, alongside notable sites like urban parks, skyscrapers, and churches. This area beautifully caters to those interested in culture and outdoor activities, ensuring a memorable holiday for all.

  • Michigan Avenue: A vibrant street known for its bustling atmosphere, Michigan Avenue boasts a mix of high-end shops, dining, and cultural attractions, making it a must-visit for those seeking the quintessential Chicago experience.
  • Chicago Riverwalk: This picturesque promenade along the Chicago River offers a delightful outdoor experience, perfect for families. Enjoy scenic views, charming eateries, and opportunities for leisurely strolls or boat tours.
  • Willis Tower: Once the tallest building in the world, Willis Tower features an observation deck with stunning city views. Its impressive architecture and iconic presence add to Chicago's city vibes.

Things to do recommended for couples

For a memorable couple's retreat in Logan Square, enjoy a concert at the vibrant Aragon Ballroom, dine at the charming Historic Michael Jordan Restaurant, or indulge in exquisite wines at Lynfred Winery. Each experience promises romance and entertainment, perfect for creating lasting memories together.

Things to do recommended for families

Families visiting Logan Square can experience the excitement of a Chicago Cubs game at Wrigley Field, enjoy the serenity of Northerly Island Natural Area, and unwind at Norridge Park District, offering plenty of space for relaxation and leisure activities.

Things to do recommended for groups

Enjoy a night out at the Vic Theatre, just 1.9km from Logan Square, for a blend of entertainment and culture. Alternatively, share some laughs at The Second City, 2.5km away, or explore the vibrant Logan Square Farmers Market for a taste of local life.

What do I need to keep in mind when booking a vacation around Logan Square

If you’re travelling with a group, as a family, bringing your pets, or seeking longer stays, be sure to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Logan Square with a group: Think about how many bedrooms you require, along with additional features like a fully-equipped kitchen or outdoor space for group gatherings. Fortunately, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Logan Square with young kids: Journeying with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities for their age, such as a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Logan Square: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Logan Square: If you’re in search of holiday rentals with discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly locate and save on monthly accommodations. You might also want to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Logan Square

Logan Square, a vibrant neighbourhood in Chicago, offers a delightful blend of urban charm and family-friendly attractions. Visitors can explore the scenic boulevards, indulge in local eateries, and enjoy the lively atmosphere at Emporium Logan Square. With its rich cultural vibe, Logan Square is perfect for those seeking a mix of outdoor adventures and romantic spots, making it an ideal destination for a memorable holiday.

  • Chicago: Chicago is a vibrant metropolis located approximately 3.1km from Logan Square. Known for its dynamic atmosphere, visitors flock to the city for a family-friendly experience filled with outdoor activities and urban exploration. Key highlights include an array of shopping areas, arena entertainment facilities, and educational venues. Don't miss iconic landmarks such as the local stadiums and the bustling tourist precinct, which offer a rich taste of the city's culture and excitement.
  • Downtown Chicago: Just 3.1km from Logan Square, Downtown Chicago is a lively neighbourhood that encapsulates the essence of city life. It's a popular destination for families and outdoor enthusiasts, offering a plethora of shopping areas, arena entertainment, and theatrical performances. The area is dotted with significant landmarks, including stadiums and a vibrant tourist precinct, making it an ideal spot to immerse yourself in the energetic atmosphere and diverse offerings of the Windy City.
  • Palmer Square: Located a mere 373m from Logan Square, Palmer Square is a charming neighbourhood perfect for families and city lovers alike. The area boasts lovely shopping spots, a picturesque recreation park, and frequent music concerts, providing a delightful urban experience. Key attractions include lush urban parks and nearby stadiums, ensuring that visitors can enjoy both relaxation and entertainment in this inviting locale.

Best time to go to Logan Square

If you're planning a trip to Logan Square, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you keen to save on your upcoming getaway? It might be worthwhile to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that suits your budget, take advantage of our filters to organise by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your travels, allowing you to initiate new trips, refine your existing plans, and manage your bookings with ease. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Logan Square?
Prices for holiday rentals in Logan Square vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Logan Square to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Logan Square holiday house rentals?
You can find great discounts on house rentals in Logan Square on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Logan Square holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Logan Square with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Logan Square?
A long-stay holiday rental in Logan Square is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Logan Square for a holiday rental?
July is the most popular time to visit Logan Square, Illinois, where the vibrant setting is at its peak during the summer months from June to August. This lively neighbourhood comes alive with outdoor festivals, street fairs, and a number of dining options, making it an ideal destination for those seeking both adventure and unique cultural experiences.

During this peak season, visitors can enjoy comfortable temperatures, typically ranging from the mid-teens to low 30s Celsius, which makes it superb for outdoor activities such as exploring the local parks or enjoying al fresco dining at one of the many trendy eateries. The lively streets are filled with people enjoying the sunshine, which adds to the overall charm of the area.

For those looking for a more budget-friendly experience, consider visiting in November. This month offers a quieter atmosphere, allowing you to enjoy the local art scene and the beautiful autumn foliage without the summer crowds. It's also a great time to explore the unique architecture and history of Logan Square at a more leisurely pace.

Ultimately, the best time to visit Logan Square for a holiday rental will depend on your preference for vibrant summer activities or a more relaxed, peaceful experience in the fall.
How early should I book a Logan Square holiday rental?
Book your Logan Square holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Logan Square, Illinois, United States of America?
In Logan Square, visitors can enjoy a mix of cultural attractions and vibrant community spaces. The Logan Square Monument, a prominent landmark, is surrounded by beautiful boulevards and parks that often host local events and farmers' markets. The area has a thriving arts scene, with the Logan Theatre showcasing independent films and performances.

For those interested in green spaces, the expansive Logan Square Park offers walking paths, playgrounds, and picnic areas, making it great for families and outdoor enthusiasts. Additionally, the neighbourhood is known for its eclectic dining options along Milwaukee Avenue, where you can find an array of restaurants and cafes that reflect the diverse culinary influences of the area.
Can I change or cancel my Logan Square home rental booking on Vrbo?
To find Logan Square holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Logan Square holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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