Logan Square holiday homes

We found 827 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

Room
Interior
Exterior
Living area
Exceptional
(11 reviews)

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

Chicago

7% off
NZ$12,964
for 7 nights, 1 home
NZ$1,852 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Exterior
Dining
Interior
Private kitchen
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
NZ$6,315
for 7 nights, 1 home
NZ$902 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Bedroom 1 - King Bed
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
NZ$14,355
for 7 nights, 1 home
NZ$2,051 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
2 spots come with the unit- occupied by the van and SUV in this photo.
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
NZ$12,836
for 7 nights, 1 apartment
NZ$1,834 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Dining room area
Living room area
Exceptional
(100 reviews)

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

Chicago

7% off
NZ$7,978
for 7 nights, 1 home
NZ$1,140 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Room
Interior
Interior
Private kitchen
Wonderful
(90 reviews)

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

Chicago

5% off
NZ$2,176
for 7 nights, 1 apartment
NZ$311 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Room
Interior
Interior
Dining
Exceptional
(18 reviews)

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

Chicago

7% off
NZ$3,183
for 7 nights, 1 apartment
NZ$455 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Kitchen (upstairs)
Downstairs living area
Downstairs living room
Fun Mirror Wall Upstairs
Exceptional
(99 reviews)

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

Chicago

7% off
NZ$15,973
for 7 nights, 1 apartment
NZ$2,282 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Interior
Room
Private kitchen
Exceptional
(12 reviews)

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

Chicago

7% off
NZ$3,687
for 7 nights, 1 apartment
NZ$527 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Living area
Belmont Harbor
Living area
Private kitchen
Exceptional
(192 reviews)

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

Chicago

14% off
NZ$8,399
for 7 nights, 1 home
NZ$1,200 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Exterior detail
Living area
Dining
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11

Chicago

7% off
NZ$3,200
for 7 nights, 1 apartment
NZ$457 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11
Exterior
Room
Interior
Living area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
NZ$4,332
for 7 nights, 1 apartment
NZ$619 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Logan Square

  • Logan Square Park: This green oasis invites visitors for leisurely strolls, picnics, and outdoor activities, perfect for families and nature lovers.
  • Architectural Gems: Marvel at the stunning architecture of local churches and historic buildings that reflect the rich heritage of the neighbourhood.
  • Cultural Vibe: Immerse yourself in the local art scene, featuring galleries and street art that showcase the area's vibrant creativity.
  • Local Cuisine: Enjoy a diverse array of eateries offering everything from casual bites to gourmet dining experiences.
  • Community Spirit: Experience the warm, welcoming atmosphere of this tight-knit neighbourhood, known for its lively streets and friendly locals.

Top attractions near Logan Square

Logan Square in Chicago, Illinois, offers a vibrant urban experience suitable for families and city enthusiasts alike. Visitors can explore Logan Square Park, enjoy the architectural beauty of local churches and skyscrapers, and immerse themselves in the unique culture of the neighbourhood. This area is perfect for outdoor activities and discovering local charm, making it an ideal stop for anyone looking to enjoy the rich community spirit of Chicago.

  • Logan Boulevard: This beautiful tree-lined avenue is perfect for strolling, featuring stunning architecture and vibrant local shops, cafés, and breweries.
  • Logan Square Farmers Market: A lively market offering fresh produce, artisan goods, and local delicacies, showcasing the community’s agricultural talent.
  • The Congress Theatre: A historic venue that hosts a variety of performances, from concerts to film screenings, reflecting the neighbourhood's cultural diversity.

Things to do recommended for couples

For a romantic getaway in Logan Square, explore the charming boulevards hand-in-hand, savour artisanal coffee at local cafes, and enjoy a leisurely bike ride along the picturesque parks. Don't miss a cosy dinner at a trendy eatery, offering delightful cuisine and intimate ambiance.

Things to do recommended for families

Families will love exploring the enchanting playgrounds at Logan Square, visiting the vibrant farmers market, and enjoying the interactive exhibits at the nearby Chicago Children's Museum. Don't miss the beautiful parklands for a relaxing picnic amid nature.

Things to do recommended for groups

Explore the vibrant Logan Square Farmers Market for local produce and crafts, or join a guided mural tour to admire the area's stunning street art. Unwind at one of the many unique breweries or grab a bite at a trendy eatery to savour the local flavours.

*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

When planning your trip, whether you're travelling with a group, as a family, with pets, or seeking longer stays, it's important to filter according to your key priorities. Here are some helpful Vrbo booking tips tailored just for you.

  • Traveling to Logan Square with a group: Consider the amount of sleeping spaces you'll require, along with features like a fully-equipped kitchen or an outdoor area for a get-together. Luckily, on Vrbo you can refine your search to include all of these and more.
  • Traveling to Logan Square with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside 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: Some families wouldn’t consider a trip complete without their furry companion. If that’s you, then explore Vrbo listings that welcome pets. Many of these accommodations offer pet bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Logan Square: If you're in search of holiday rentals that offer great deals for stays of a month or more, you've come to the right spot. 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

Discover the vibrant urban charm of Logan Square in Chicago, a neighbourhood that offers a blend of family-friendly vibes and city sophistication. Stroll its tree-lined streets, enjoy lush parks, and explore local art and culture. This destination invites you to experience both lively streets and serene corners, making it a perfect base for urban adventures and relaxed moments in the heart of Chicago.

  • Chicago: Chicago, a vibrant metropolis, is known for its stunning architecture and rich cultural scene. Situated around Logan Square, it offers a myriad of attractions that appeal to families and outdoor enthusiasts alike. Visitors can explore the bustling shopping areas, enjoy arena entertainment, or take in a show at one of the many theatres. Notable landmarks include iconic sports stadiums and expansive urban parks, providing ample opportunities for recreation and relaxation. The city’s diverse culinary landscape and dynamic neighbourhoods make it an exciting destination to experience urban life.
  • Downtown Chicago: Located approximately 8km from Logan Square, Downtown Chicago is a bustling hub that embodies the city's energy and charm. This area is perfect for family outings, outdoor activities, and city exploration. Visitors can indulge in shopping, catch a thrilling game at a sports facility, or enjoy a theatrical performance. The proximity to major attractions like urban parks and tourist precincts makes it a convenient base for exploring the city’s highlights. The vibrant atmosphere and stunning skyline contribute to a memorable travel experience.
  • Bucktown: Bucktown, just 3km from Logan Square, is a trendy neighbourhood that combines artistic flair with a family-friendly vibe. Known for its lively theatre scene and music concerts, this area offers a unique cultural experience. Visitors can unwind in local recreation parks or attend events at various conference venues. The blend of urban parks and entertainment options makes Bucktown an inviting spot for those seeking both relaxation and activity in a charming setting.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverage
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudyAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly High
May57.0°F (13.9°C)Light RainMostly SunnyAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly Low
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as this can lead to varying prices. Additionally, extending your stay often brings about 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 space where you can create new journeys, continue planning, or review and organise your bookings. Properties you’ve saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

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.
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.
Are all fees included in the Logan Square holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Logan Square holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Logan Square holiday homes?
You can find great discounts on holiday homes in Logan Square on Bookabach, 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.
Can I change or cancel my Logan Square holiday home booking on Bookabach?
To find Logan Square holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Logan Square?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Logan Square holiday home?
Book your Logan Square holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Logan Square?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Logan Square to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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