Logan Square holiday lettings

We found 833 holiday rentals — enter your dates for availability
Discover a selection of 15 homes, 44 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.

Holiday rentals with weekly discounts – Logan Square

Showing deals for:18 Dec - 25 Dec

Living area
Interior
Exterior
Room
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

7% off
£5,589
for 7 nights, 1 home
£798 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Private kitchen
Dining
Exterior
Interior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
£2,784
for 7 nights, 1 home
£398 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Kitchen on Top Floor
Top floor kitchen and dining area
Bedroom 3 w/ Queen Bed
Dining Area
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
£5,594
for 7 nights, 1 apartment
£799 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Bedroom 1 - King Bed
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
£5,845
for 7 nights, 1 home
£835 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Living room area
3 bedroom unit is top floor of historic greystone
Dining room area
View of Robey Hotel from back deck
Exceptional
(100 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
£3,570
for 7 nights, 1 home
£510 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Kitchen (upstairs)
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
£6,853
for 7 nights, 1 apartment
£979 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Interior
Private kitchen
Interior
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
£1,613
for 7 nights, 1 apartment
£230 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Room
Interior
Private kitchen
Dining
Exceptional
(18 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
£1,350
for 7 nights, 1 apartment
£193 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Interior
Interior
Living area
Room
Wonderful
(91 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
£940
for 7 nights, 1 apartment
£134 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Living area
Belmont Harbor
Private kitchen
Living area
Exceptional
(192 reviews)

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

Chicago

14% off
£3,773
for 7 nights, 1 home
£539 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Exterior detail
Room
Living area
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23

Chicago

7% off
£1,369
for 7 nights, 1 apartment
£196 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23
Exterior
Room
Private kitchen
Living area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
£1,916
for 7 nights, 1 apartment
£274 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Logan Square

  • Picturesque parks: Enjoy leisurely strolls and community events in the scenic Logan Square Park.
  • Rich cultural heritage: Discover striking urban architecture and historic churches that reflect the area's unique character.
  • Eclectic dining: Savor a diverse range of eateries offering delicious and unique culinary experiences.
  • Arts scene: Immerse yourself in local arts and culture, showcasing the vibrant spirit of the community.
  • Charming neighbourhood: Explore historic boulevards and local boutiques for a delightful shopping experience.

Popular types of accommodation around Logan Square

Logan Square, a vibrant neighbourhood in Chicago, Illinois, offers a diverse selection of accommodations for travellers seeking a unique experience. Popular options include stylish apartments, spacious houses, and modern condos, perfect for families or solo explorers. While staying in Logan Square, immerse yourself in the local culture by visiting the picturesque boulevards, enjoying nearby parks, and discovering eclectic dining and shopping options that capture the essence of this lively community.

  • Flats: The most sought-after accommodation in Logan Square, offering a comfortable and modern living space for visitors.
  • Private Holiday Homes: A popular choice for families or groups, providing ample space and a home-like atmosphere.
  • Condos: These stylish units often feature amenities and convenient locations, perfect for a city escape.
  • Cottages: Quaint and charming, cottages offer a unique stay with a homely feel in a picturesque setting.**

Top attractions near Logan Square

Logan Square, Chicago, Illinois, offers a vibrant neighbourhood perfect for family and outdoor vacations. Explore the scenic Logan Square Park, where you can enjoy leisurely strolls and community events. The area is also home to striking urban architecture and historic churches, providing a rich cultural experience. Whether you're seeking relaxation or family-friendly activities, Logan Square has something to captivate every traveller.

  • Logan Square: A vibrant neighbourhood known for its eclectic mix of historic architecture and modern amenities, Logan Square boasts a lively arts scene, charming boutiques, and an array of eateries offering diverse cuisines, perfect for leisurely strolls.
  • Logan Boulevard: This picturesque boulevard features beautiful tree-lined streets and stunning historic homes, ideal for a relaxing walk or bike ride, showcasing the area's charming residential character.
  • Palmer Square Park: A lovely green space where locals gather for community events, picnics, and recreational activities, offering a serene escape amidst the urban hustle.

Things to do recommended for couples

Logan Square offers charming activities for couples, like a leisurely walk through the picturesque boulevards or a romantic dinner at a cosy bistro. Don't miss the vibrant local art scene and a sunset picnic in the park to create lasting memories together.

Things to do recommended for families

Families will delight in exploring the beautiful gardens at the Chicago Botanic Garden, just a short drive away, or enjoy the interactive exhibits at the nearby Science and Industry Museum. Don't miss the vibrant local art scene and parks perfect for picnics and play.

Things to do recommended for groups

Explore the vibrant local art scene at the Logan Square Arts Festival or indulge in a group food tour sampling Chicago's famous deep-dish pizza at local eateries. Don't miss the chance to relax in the scenic Logan Boulevard Park for a delightful picnic.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with a group, family, or pets, or if you're seeking extended accommodation, be sure to sort 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 features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and much more on Vrbo.
  • Traveling to Logan Square with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Logan Square: For many, a family holiday isn’t truly enjoyable without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Logan Square: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Logan Square

Logan Square, a vibrant neighbourhood in Chicago, offers a delightful mix of urban charm and family-friendly experiences. Visitors can enjoy picturesque parks, eclectic eateries, and a rich arts scene that captures the essence of city life. Stroll along the historic boulevards, explore local boutiques, or relax in the green spaces that make this area so inviting. With its unique vibe, Logan Square promises a memorable getaway filled with culture and community spirit.

  • Chicago: As a bustling metropolis, Chicago is a vibrant hub of culture and activity. Logan Square is nestled within this expansive city, making it an ideal base for exploration. Visitors flock to Chicago for family-friendly adventures, outdoor activities, and the urban atmosphere. The city's array of attractions includes shopping districts, arena entertainment facilities, and a plethora of theatres. Notable landmarks nearby encompass sports stadiums, popular tourist precincts, and scenic urban parks, ensuring that there’s something for everyone to enjoy.
  • Downtown Chicago: Located approximately 8km from Logan Square, Downtown Chicago is the city's vibrant heart. This neighbourhood offers a lively blend of family-oriented activities, outdoor experiences, and urban charm. Guests will be drawn to its shopping areas, lively arenas, and theatres that showcase world-class performances. With a host of attractions such as tourist precincts, sports facilities, and lush urban parks, Downtown Chicago provides an engaging experience for all visitors seeking the excitement of city life.
  • Palmer Square: Just 966m away from Logan Square, Palmer Square offers a delightful mix of family activities, outdoor enjoyment, and a city-like feel. This charming neighbourhood is known for its recreation parks, music concerts, and vibrant theatre scene. With landmarks including urban parks, sports stadiums, and cultural centres, Palmer Square invites visitors to immerse themselves in the local community spirit while enjoying a variety of recreational opportunities.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to better prices. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated area for you to plan new journeys, manage ongoing arrangements, or review and organise your bookings. Your saved or reserved 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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