Holiday houses in Kathy Osterman Beach

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

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.

lakefront apartment

This is located steps away from Ardmore Avenue Beach on Sheridan Rd (chicago city street noise), with it's running and biking trails seen from apartment. Less than 5 min walk to bus and train stops - easy access to a variety of areas and attractions, including the Magnificent Mile and the John Hancock Center. Also a few blocks away from Loyola University (beautiful serene view points of the lake). The apartment is cozy with intentional design touches that will make you feel right at home.

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont 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.

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

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.

Urban Garden Retreat, Chic Andersonville Getaway

Fully renovated 2-bedroom, 1-bath garden level apartment just steps away from all the amazing restaurants and shops in the Andersonville neighborhood. 95 Walk Score (Very Walkable) 72 Transit Score (Excellent Transit) 75 Bike Score (Very Bikeable with a Divvy bike rental 0.2 miles away) 0.7 miles to the lake 0.8 miles to Little Vietnam 1.1 miles to Loyola University 2.5 miles to Wrigley Field

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...