Logan Square holiday homes
We found 780 holiday rentals — enter your dates for availability
Discover a selection of 16 homes, 55 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 Jul - 25 Jul
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$15,130
NZ$15,130
NZ$2,161 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,396
NZ$11,396
NZ$1,628 per night
includes taxes & fees
Image gallery for Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

1010 out of 10 rating
Exceptional
(8 reviews)
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Chicago, IL
12% off
Price is NZ$7,470
NZ$7,470
NZ$1,067 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home

1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
12% off
Price is NZ$11,054
NZ$11,054
NZ$1,579 per night
includes taxes & fees
Image gallery for Large 2-Bedroom w/ Huge Roofdeck view of Skyline

9.29.2 out of 10 rating
Wonderful
(5 reviews)
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Chicago, IL
9% off
Price is NZ$5,407
NZ$5,407
NZ$772 per night
includes taxes & fees
Image gallery for Spacious Downtown Chicago Condo with Spa Bath, King Bed, Patio, 3 Blocks to L

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Spacious Downtown Chicago Condo with Spa Bath, King Bed, Patio, 3 Blocks to L
Chicago, IL
6% off
Price is NZ$5,869
NZ$5,869
NZ$838 per night
includes taxes & fees
Image gallery for Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

1010 out of 10 rating
Exceptional
(34 reviews)
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
8% off
Price is NZ$4,059
NZ$4,059
NZ$580 per night
includes taxes & fees
Image gallery for Luxury 4-Bedroom Retreat in Chicago

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury 4-Bedroom Retreat in Chicago
Chicago, IL
32% off
Price is NZ$16,072
NZ$16,072
NZ$2,296 per night
includes taxes & fees
Image gallery for Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10
Chicago, IL
8% off
Price is NZ$23,294
NZ$23,294
NZ$3,328 per night
includes taxes & fees
Image gallery for Modern 4 Bedroom Apt Next to Park&Pool | Lakeview

9.89.8 out of 10 rating
Exceptional
(55 reviews)
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
Chicago, IL
11% off
Price is NZ$8,923
NZ$8,923
NZ$1,275 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Chicago, IL
8% off
Price is NZ$4,180
NZ$4,180
NZ$597 per night
includes taxes & fees
Image gallery for Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Chicago, IL
16% off
Price is NZ$3,748
NZ$3,748
NZ$535 per night
includes taxes & fees
Image gallery for Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

8.08.0 out of 10 rating
Very good
(5 reviews)
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Chicago, Illinois
8% off
Price is NZ$22,074
NZ$22,074
NZ$3,153 per night
includes taxes & fees
Image gallery for Wicker Park. 3-Level Home. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage.

9.89.8 out of 10 rating
Exceptional
(20 reviews)
Wicker Park. 3-Level Home. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage.
Chicago, IL
8% off
Price is NZ$13,777
NZ$13,777
NZ$1,968 per night
includes taxes & fees
Image gallery for Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown

1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
Chicago, IL
12% off
Price is NZ$5,062
NZ$5,062
NZ$723 per night
includes taxes & fees
Image gallery for *Comfortable & Spacious Home Close to Downtown*

9.49.4 out of 10 rating
Exceptional
(14 reviews)
*Comfortable & Spacious Home Close to Downtown*
Chicago, IL
8% off
Price is NZ$9,683
NZ$9,683
NZ$1,383 per night
includes taxes & fees
Image gallery for Modern 2 King BR Apt, Relax in Style!!

9.69.6 out of 10 rating
Exceptional
(44 reviews)
Modern 2 King BR Apt, Relax in Style!!
Chicago, IL
8% off
Price is NZ$3,990
NZ$3,990
NZ$570 per night
includes taxes & fees
Image gallery for 33rd-Floor 2000ft² PH Near Fulton Market|TheHarper

9.29.2 out of 10 rating
Wonderful
(5 reviews)
33rd-Floor 2000ft² PH Near Fulton Market|TheHarper
Chicago, IL
8% off
Price is NZ$26,287
NZ$26,287
NZ$3,755 per night
includes taxes & fees
Image gallery for Chic, Cozy home, by Blue Line Train Stop + Free parking

9.49.4 out of 10 rating
Exceptional
(46 reviews)
Chic, Cozy home, by Blue Line Train Stop + Free parking
Chicago, IL
5% off
Price is NZ$3,006
NZ$3,006
NZ$429 per night
includes taxes & fees
Image gallery for Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Chicago, IL
16% off
Price is NZ$12,919
NZ$12,919
NZ$1,846 per night
includes taxes & fees
Image gallery for Light and bright 3BD duplex in Avondale, Chicago

1010 out of 10 rating
Exceptional
(22 reviews)
Light and bright 3BD duplex in Avondale, Chicago
Chicago, IL
16% off
Price is NZ$4,613
NZ$4,613
NZ$659 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Logan Square
Map Attractions

1
Illinois Centennial Memorial Column
Find the best place to stay - Logan Square
Bright/Cozy/Hip 2/1 Apt | Logan Square
Sleeps 5 · 2 bedrooms · 1 bathroom
7.87.8 out of 10
Goodgood
11 reviews(11 reviews)
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Family-friendly, stylish Chicago Apartment in Logan Square
Sleeps 7 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Chicago Dickens place 1 bd. Garden unit Centralized loc.
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
30 reviews(30 reviews)
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
271 reviews(271 reviews)
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Logan Square?
The most in-demand types of holiday homes in Logan Square are apartments. Prefer something different? Bookabach offers a variety of options to match our guests’ requirements, so you’ll see holiday homes in all sizes and shapes. The ideal fit is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Logan Square?
The average price for a holiday home in Logan Square is determined by several factors, including length of stay, property type and season. Whether you’re thinking about a villa with space for extended family or a quaint cabin just enough for two, just add your dates of travel to view stays that offer great value.
How much does it cost to rent a beach house in Logan Square?
The average price for a holiday home near the beach in Logan Square depends on when you’re travelling and the size and type of property you’re looking for. Find prices quickly and easily on Bookabach by entering your dates of travel. Then use the handy filter tool to choose the number of bedrooms and amenities that you require, like WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Logan Square?
Good news! Yes. You’ll have your pick of 42 holiday homes that allow pets in Logan Square. Plenty of our pet-friendly holiday homes come with space outdoors for your fur child to play around in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find a pad that’ll get tails wagging on Bookabach.
Can I rent a house with a pool in Logan Square?
Check the “pool” box in our handy filter tool and choose from five houses with private pools in Logan Square on Bookabach. Morning swim, sunset soak or midnight dip? Downtime is up to you when your holiday property has its own swimming pool.
What are popular home amenities in Logan Square?
Some of the most popular home amenities people search for in Logan Square are a garden, nearby museums and a fireplace. Whether you’re on the road with family, your besties or even pets, Bookabach holiday homes provide the best amenities for making new memories with the people that matter most.
Are there large group holiday homes in Logan Square?
Logan Square has six holiday properties that can host 10 or more people. These stays come with the space you need to enjoy good times with loved ones.
Are there holiday homes in Logan Square that welcome kids?
With 42 family-friendly holiday properties available in Logan Square, now is a great time to introduce the kiddos to the excitement of travel. Click on our “Properties good for families” filter box to search for stays loaded with amenities ideal for holidaying families, such as kitchens, private pools, entertainment areas and bunk beds.
What are the top attractions for families in Logan Square?
Keeping the kids happy during your Logan Square holiday is simple with these leading family-friendly attractions:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there one-bedroom holiday homes in Logan Square?
You’ll find seven one-bedroom properties in Logan Square to choose from. A one-bedroom holiday property is a wonderful option if it’s only two of you or if you’re travelling solo. Throw in more space, convenience and privacy than a hotel, and you’re bound to have a break to remember.
Can I find two-bedroom holiday homes in Logan Square?
Gather your besties and enjoy peace, privacy and comfort in one of the 16 two-bedroom holiday homes Logan Square has to offer.
Are there holiday homes with WiFi in Logan Square?
Logan Square has six holiday homes with WiFi, so you can stay connected when you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Bookabach homes make it a cinch to get online.
How can I find holiday homes with air conditioning in Logan Square?
You can choose from 39 holiday homes with air conditioning in Logan Square offering that cooling breeze and extra comfort level. Enter your preferred travel dates and then use our handy filters to help you find stays with air conditioning.
How old do you have to be to rent a holiday home in Logan Square?
The minimum age is generally 16, 18 or 21. It can differ from one property to another on Bookabach, so look at the rules of your preferred Logan Square holiday home before booking your escape.
How long can I rent a holiday home in Logan Square for?
It’s up to the Logan Square property. To look at a list of options offering extended stays, simply enter your travel dates and number of guests into Bookabach’s search page. You can look forward to having the whole place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space to run around in. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.