Vacation rentals in Jackson Park, Chicago

2 br, 2 bt, UChicago Coachman's Guesthouse

This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChicago main quad. Situated on a quiet residential street. Full kitchen to prepare your own meals and dedicated laundry. Easy access from O'Hare or Midway airports. Less than 2 blocks from the Metra train to downtown, Mccormick Place, Soldier Field, Wintrust Arena, Grant Park and Millenium Park. Walk to Trader Joe's, Walgreens, restaurants, lakefront, stores, museums and more.

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

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, 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 Griffen Museum of Science and Industry, 20 minutes to Soldier Field, Millinneum Park, Downtown, Navy Pier

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.

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

Modern Soul Retreat: 3BR in Bronzeville/HydePark

Experience a modern sanctuary where design meets history in the heart of Chicago’s legendary Bronzeville. This spacious 3-bd, 2-ba flat blends art, minimalist comfort, and cultural warmth. Steps from Hyde Park, Lake Michigan, and local cafes, the space invites you to unwind, reflect, and reconnect with the soul of the South Side. Featuring curated decor, luxury finishes, and a nod to Bronzeville’s Soulful Metropolis legacy, this home offers a one-of-a-kind stay—equal parts style and heritage.

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.

Explore Chicago • Private Parking • Museum Access

Esther & Lily is a historic Chicago bungalow where visitors can relax, work, move, and explore the city. Coming to Chicago for college move-in, campus visit, museums or a fall getaway? Esther & Lily is a home away from home with 3 sleeping spaces, 2 bathrooms, full kitchen, dining, dedicated workspace, multiple sitting areas, a sun room, free street parking, private driveway, self check-in, and garage access. Flexible check in times from now until November 1st.

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

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 Obama Museum 63rd Street Beach Museum of Science and Industry La Rabida Children’s Hospital University of Chicago Hyde Park

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.

Modern Eco Stay • UChicago • Parking • Backyard

Relax in this eco-friendly South Side retreat designed for comfort, style, and convenience. Located minutes from UChicago, Hyde Park, Jackson Park, the Museum of Science & Industry, and the lakefront, this unit is perfect for families, medical visits, students, and anyone exploring Chicago. With a private entrance, free parking, and a large fenced backyard, this modern space gives you privacy and peace in the city.