Holiday houses in Jackson Park, Chicago

South Shore Dr Retreat

Enjoy easy access to everything from this perfectly located home base. Walking distance to a 9 hole golf course, beach, and famous Lake Michigan lakefront bike and walking path. Commuters dream with easy access to Chicago bus line and Metra train station. You are close to the following Chicago locations: Lake Michigan lakefront path La Rabida Children’s Hospital 63rd Street Beach Museum of Science and Industry Obama Museum(opening planned in first half of 2026) University of Chicago Hyde Park

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

Luxury Condo | Spa Bath | Full Kitchen | FREE PRKG

Enjoy a luxurious escape in this modern Bronzeville home where style meets comfort. Designed with contemporary finishes, cozy textures, and a serene vibe, it’s perfect for couples, families, friends, or business travelers. Easily accessible to UChicago, McCormick Place, Soldier Field, Shedd Aquarium. With quick freeway access to I-90 & Lakeshore Drive, Downtown Chicago is just minutes away! Relax, unwind, and enjoy free street parking plus all the essentials for a premium Chicago stay.

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Modern Haven in Little Village

Step into The Artistic Brick Loft, featuring modern amenities and artistic flair. The bedroom includes ample storage and unique décor. The living area boasts an exposed brick wall, chic furniture, and captivating artwork. The kitchen offers modern appliances and a dining area. The bathroom features a sleek design with a walk-in shower. In-unit laundry and easy street parking compared to other city locations ensure a hassle-free stay. Enjoy comfort and style.

Bright & Cozy Studio in the Heart of Hyde Park

Cozy, sunlit Hyde Park studio just blocks from UChicago. Enjoy a comfy queen bed, private bath, fast Wi-Fi, and a fully stocked kitchen with all essentials. Nestled on a quiet, tree-lined street in a safe, walkable neighborhood near cafés, restaurants, parks, and museums. Easy CTA and Metra access for downtown trips. Perfect for solo travelers, couples, and visiting academics seeking comfort, convenience, and a welcoming, homey atmosphere.

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Stylish Studio Getaway – Close to University

Welcome to your serene retreat in the heart of Hyde Park. This beautifully appointed studio apartment offers a harmonious blend of historic charm and modern amenities, perfect for solo travelers, visiting scholars, or couples exploring Chicago.