Holiday houses in Jackson Park, Chicago

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

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.

UChicago Luxurious King Suite Lakefront

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

The Reset Space • A Minimalist 1BR Oasis

Welcome to The Reset Space • A Minimalist 1BR Oasis, a Dwell Well Here property! 🧘🏾‍♂️✨ Discover a spacious haven nestled in the heart of a historic Chicago neighborhood. We’ve intentionally designed this apartment to be your personal "reset" button—blending the convenience of city living with the quiet, airy comfort you need to recharge. Whether you’re here for a weekend getaway or a deep-work retreat, this minimalist oasis offers the perfect balance of soul, style, and serenity. 🌿🏡

You are my Muse!

Allow the Muse to be your home away from home. It provides luxury and comfort. Its unique decor was chosen with you in mind. The Muse is filled with energy that captures your artistic eye. Each room tells a story. Each piece was carefully selected. It sleeps 4-6 and has space to entertain. The Muse is nestled in the heart of Woodlawn. The expansive unit, has one full and two half baths. Each has a spa-like feel; especially the full bath that is easily accessible through the masons.

Historic Spacious Chicago Home • Free Parking

Esther & Lily is a historic Chicago bungalow where visitors can relax, work, and explore the city. A home away from home, this Guest Favorite features 3 sleeping spaces, a dedicated workspace, dining room, multiple sitting areas, a fully equipped kitchen, free parking, and self check-in. Conveniently located near Hyde Park, the University of Chicago, museums, the lakefront, the Obama Presidential Library, and downtown, Esther's Abode is the perfect home base for your stay.

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.

UChicago Condo | 2 Baths, Private Parking & Entry

Enjoy the convenience of a dedicated private parking space with direct access to your own private entrance. This upgraded and spacious 1-bedroom, 2-bathroom condo near the University of Chicago features hardwood floors, stainless steel appliances, in-unit laundry, two Smart TVs, a cozy reading nook, and a large outdoor patio. Conveniently located near Hyde Park, Lake Michigan, Jackson Park, and the Obama Presidential Center. Perfect for extended stays and remote work.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Luxe Loft vibe | King Suite |4BR 3Ba

Stay in style near Chicago’s best! This luxe 4BR, 3BA loft is perfect for families, professionals, or UChicago guests. Enjoy a king suite with jacuzzi, 3 queen bedrooms with desks, and an open layout with smart TVs, exposed ducts, and dining for 10. Walk to the Obama Presidential Center, Museum of Science & Industry, and lakefront. Adjacent to Hyde Park with quick downtown transit—just 50 min to Indiana Dunes!

Relaxed Hyde Park Studio Getaway Near Downtown

Stay in the heart of Hyde Park in this comfy studio just steps from the University of Chicago, 53rd Street shops, cafés, and the lakefront. The space has a queen bed, full kitchen, Roku TV, and in-unit washer/dryer, making it easy to settle in. Bright and thoughtfully decorated, it’s a perfect spot to relax after exploring the neighborhood. Easy access to Metra and buses gets you downtown in minutes.