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Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Edgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

1910 Beautiful Restoration! Walk to Beach!

Welcome to this thoughtfully preserved 110 year old, original Chicago brick home, just 3 blocks from the Lake Michigan shoreline. Lots of charm and character in this storied home with a serene backyard oasis in the heart of the city! While this historical gem is the perfect private getaway for you & family, its location makes it easy to get around. You are: 1 Block to L train, Sushi, Thai, Coffee, Loyola 15 min: Wrigley 18 min: Downtown *We also have a 2nd unit to house a total of 16.

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Private Garden Apartment GATED FREE Parking

This garden apartment is within the main house. Your cozy apartment has its own entrance with has a nice sized bedroom with queen bed, along with a living room with a coffee table, a new Crate and Barrel deep cozy sofa that can sleep a third guest, bathroom with a shower, and an office room with a desk, STOCKED mini fridge and coffee/tea station and mini oven. Free gated parking will also be available 24/7.

Jean's House—Restored Historic Andersonville Craftsman

Renovated for AirBNB, the 2 bedroom, 1 bath unit has a full kitchen and in-unit washer and dryer; as well as bay windows that overlook the new park across the street. The unit is located in the heart of Andersonville and comfortably hosts 4 guests. Take a short stroll to discover the many restaurants, cafes, and independent stores of Andersonville, known as the “Shop Local Capital of Chicago”.

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

Andersonville Garden Living

This is an amazing garden level apartment right off Clark st. with all the shops and restaurants right down the block. Grab a coffee at the Coffee Studio or a drink at Little Bad Wolf . This unit has a brand new kitchen and has a Smart TV with Netflix and a huge living room to hang out, and new bathroom with a large shower. It also has a private bedroom and access to laundry.