Logan Square holiday rentals

We found 824 holiday rentals — enter your dates for availability
Discover a selection of 16 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:4 Dec - 11 Dec

Exterior
Living area
Living area
Interior
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

8% off
AU$7,057
for 7 nights, 1 home
AU$1,008 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Living area
Interior
Private kitchen
Interior
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
AU$6,576
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Dining Area
Top floor kitchen and dining area
Bedroom 3 w/ Queen Bed
Kitchen on Top Floor
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$8,790
for 7 nights, 1 apartment
AU$1,256 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
Living Room with 60 in Smart TV
Exceptional
(91 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$8,671
for 7 nights, 1 home
AU$1,239 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Dining
Private kitchen
Exterior
Exceptional
(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
AU$3,722
for 7 nights, 1 home
AU$532 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Interior
Interior
Property grounds
Private kitchen
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
AU$3,357
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Living room area
3 bedroom unit is top floor of historic greystone
Dining room area
Living room area opens into dining room & kitchen
Exceptional
(98 reviews)

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

Chicago

7% off
AU$6,321
for 7 nights, 1 home
AU$903 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Living area
Interior
Room
Interior
Exceptional
(12 reviews)

Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!

Chicago

11% off
AU$6,341
for 7 nights, 1 villa
AU$906 per night
includes taxes & fees
Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!
Dining
Private kitchen
Interior
Interior
Wonderful
(49 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
AU$4,638
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Living area
Interior
Interior
Private kitchen
Wonderful
(86 reviews)

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

Chicago

5% off
AU$1,487
for 7 nights, 1 apartment
AU$212 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Living area
Living area
Interior
Private kitchen
Exceptional
(13 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

25% off
AU$5,904
for 7 nights, 1 apartment
AU$843 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Interior
Interior
Room
Private kitchen
Exceptional
(17 reviews)

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

Chicago

7% off
AU$2,221
for 7 nights, 1 apartment
AU$317 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Interior
Interior
Private kitchen
Room
Exceptional
(12 reviews)

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

Chicago

7% off
AU$2,974
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Upstairs queen bedroom 2
Downstairs living area
Fun Mirror Wall Upstairs
Kitchen (upstairs)
Exceptional
(98 reviews)

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

Chicago

7% off
AU$12,317
for 7 nights, 1 apartment
AU$1,760 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Exterior
Belmont Harbor
Private kitchen
Living area
Exceptional
(191 reviews)

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

Chicago

14% off
AU$5,576
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Dining
Living area
Room
Interior
Exceptional
(27 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
AU$2,264
for 7 nights, 1 apartment
AU$323 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Private kitchen
Exterior detail
Dining
Living area
Exceptional
(69 reviews)

Wicker Park near Downtown and the Salt Shed Special 149.00 Sept 7-12

Chicago

7% off
AU$2,363
for 7 nights, 1 apartment
AU$338 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 149.00 Sept 7-12
Living area
Kitchen
Living area
Kitchen
Exceptional
(13 reviews)

Large 2-Bedroom w/ Huge Roofdeck view of Skyline

Chicago

8% off
AU$2,306
for 7 nights, 1 apartment
AU$329 per night
includes taxes & fees
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Children’s area
Private kitchen
Exterior
Living area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
AU$3,251
for 7 nights, 1 apartment
AU$464 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

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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Logan Square holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Logan Square to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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