
Apartment holiday rentals in Logan Square
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Top-rated apartment rentals in Logan Square
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Logan Square Cozy 2BR Basement Apartment
Beautiful Logan Square Basement 2BR Apartment recently updated, perfect for small groups of friends and family. Fully stocked with all the necessary amenities to make you feel right at home. Incredible location with fenced yard on the historic Boulevard in one of Chicago's trendiest neighborhoods. A variety of walkable amenities include: Blue line train station, bars, restaurants, coffee shops, pharmacy, and grocery store. Quick commute to Downtown, O'Hare. One dog under 80 pounds is welcome.

Serene Logan Sq Apt | Walk to Dining & Blue Line
Step into the vibrant heart of Logan Square and experience the comfort of this classic, Chicago-style apartment, just one block from Logan Square Boulevard. Perfect for guests exploring the city or visiting family in the neighborhood, this updated space blends modern amenities with vintage character. You’re steps from top restaurants, bars, coffee shops, and the Logan Square Farmer’s Market. Downtown attractions like Navy Pier and Millennium Park are easily accessible via the Blue Line or Uber.

2BR Centrally Located in Cozy Hip Logan Square
Explore one of Chicago's most popular neighborhoods, Logan Square, home to hipsters, artists, techies and foodies. I am inclusive and welcome all! The bnb is 1.5 blocks from the El blue line direct from O'hare airport, 25 minutes to downtown Chicago (via El blue line), and a 15 minute drive to the United Center. You can walk to plenty of great restaurants, bars, parkland space, and in the summer, Italian ice and a great farmer's market every Sunday. There is plenty of street parking.

Cozy and Comfy 1BR Apartment in Logan Square!
Welcome to Chicago! Our 1-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. It's professionally designed with modern furniture and located in the trendy Logan Square neighborhood. Designated parking spot is NOT available, but there is plenty of street parking. NOTE: -This is a basement unit with a low ceiling ( HEIGHT: 5.9 ft.). ONLY SUITABLE FOR SOMEONE AROUND or UNDER 5.8 FT. -There are two windows in the bedroom and two windows in the living room for natural light.

Humboldt Park Loft
Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Colorful & Peaceful Boho-Chic Unit in Logan Square
Kick back & relax in your home away from home in our stylish, spacious and peaceful abode in the center of the Logan Square neighborhood, close to downtown and the CTA Blue Line. Featuring incredible natural light, modern amenities & beautiful artwork, the apartment is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Milwaukee Avenue, you're only blocks away from local breweries, restaurants, coffee shops and much more!

Private Logan Square Studio
A private second floor walk up vintage studio apartment right in the heart of Logan Square. Located just half a block north of the picturesque Logan Boulevard and three blocks (5-8 minute walk) from the Logan Square blue line stop which is great for getting around the city. Logan Square is a 15 minute train ride into the loop and 20 minutes out to O'Hare. This studio is convenient for the weary O'Hare traveler or perfect for a private getaway from the hustle of Chicago.

Bright & Cozy 1-Bedroom Apartment in Logan Square
Bright and charming top floor apartment in the trendy Logan Square neighborhood. Located on a quiet tree lined residential street with multiple restaurants, bars, and coffee shops within walking distance. The CTA blue line station is an easy 20min walk or 10min bus ride away. Or hop on a Divvy Bike; the rental station is located at the end of the block. The 606 Bloomingdale Trail is less than 2 blocks away and is your direct route to endless amenities and destinations.

Bright, Spacious 2BR Apt In Heart of Logan Square!
Live like a local in this charming 2 bed, 1 bath garden apartment in a classic Chicago two-flat in Logan Square. Renovated top to bottom, the space is stylish, cozy, and full of character. Just a 5-min walk to the Blue Line, top restaurants, cafes, and shops. Grab coffee from a nearby café and explore the city, or hit the Sunday farmers market for local flavor. Logan Square is one of Chicago’s most vibrant neighborhoods—and this home puts you right in the heart of it.

Right in the heart of Logan Square.
BEST LOCATION IN LOGAN SQUARE!! Brand new stylish 3 bed, located in the heart of the highly desirable Logan Square neighborhood. This luxurious space is situated right by the historic Logan Square Boulevard, literally 10 STEPS AWAY from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Logan Square Garden
This 3-bedroom garden apartment anchors a Victorian home in one of Chicago's coolest neighborhoods. It's convenient, clean & cozy on a quiet, tree-lined residential block, steps from restaurants, nightlife, retail, etc. We're 5 blocks from the Logan Square CTA Blue Line stop, midway between O'Hare & downtown Chicago. Private entry, new kitchen and bath, Wi-Fi, desks & comfy beds. Nice and affordable for a couple, but the apartment can accommodate up to 5.

Cool City Comfort - Logan Sq. - O’Hare CTA
Our 1st floor apartment and it’s location in Avondale/Logan Square will leave you impressed. Only a quick walk to the Logan Sq CTA Blue Line stop and our street is full of families and long time residents. Free street parking. 5 guests total are allowed, but additional fee for more than 3 guests. If you are a family larger than 3 traveling with children, fee is negotiable, please mention it. PLEASE read the ADDITIONAL RULES and OTHER DETAILS TO NOTE.
Popular amenities for Logan Square apartment rentals
Weekly apartment rentals

Evanston 2BR 2Bth 1 Blk to Beach

iKlektik House Chicago/BlueJay

Spacious Studio w/Balcony in Bucktown/Wicker Park

💙⚾️ 💙Great Apt, 3 miles West of Wrigley Field 💙⚾️💙

Explore Lincoln Park from a Polished Apartment

Attic apartment in a hip neighborhood!

Cozy Bucktown/Logan Square Close to everything

3br W/ Elevator, Patio & Laundry Near the Red Line
Private apartment rentals

Chic retreat near the best of Lakeview & Wrigley

Pilsen Modern Chic Retreat

Ina's Beachwood Inn In the Heart of Wicker Park

Prime Logan Square apartment

Quirky Quarters at Wrigley

Logan Video Game Studio

Lovely top floor Apt in Logan Sq

Modern+Spacious W/King Bed, Walk to Town-Park Free
Apartment rentals with a hot tub

Spacious and Ideally located in the Lakeview area

Super Paradise+65 Amenities*Downtown 15 Min

Jacuzzi , private master bath and master bedroom

Spacious 2bdm unit 15min to Dwtn

Chicago Chinatown Center A

Belmont Pleasures - hot tub / arcade gaming room

The Downtown Oasis (Indoor Pool • Fitness Center)

Bronzeville Escape
Quick stats about flat rentals in Logan Square

Total holiday rentals
Explore 270 holiday rentals in Logan Square

Nightly prices starting at
Logan Square holiday rentals start at $26Â SGD per night before taxes and fees

Verified guest reviews
Over 27,000 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
270 of Logan Square holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Logan Square rentals

4.8 Average rating
Logan Square stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a fireplace Logan Square
- Rentals with a patio Logan Square
- Rentals with a firepit Logan Square
- Hotel rooms Logan Square
- Fitness-friendly rentals Logan Square
- Apartment rentals Logan Square
- Pet-friendly rentals Logan Square
- Rentals with outdoor seating Logan Square
- Family-friendly rentals Logan Square
- Rentals with a washing machine and dryer Logan Square
- Flat rentals Chicago
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Wilmot Mountain Ski Resort
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach





