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.

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

Bronzehaus - near McCormick, UChicago & Downtown

Welcome to Bronzehaus – a chic retreat in the heart of historic Bronzeville. Bronzehaus is a newly renovated, thoughtfully designed 2-bedroom, 1-bath garden-level apartment blending comfort and class. Inspired by the rich jazz legacy and artistic soul of the area, this stylish space features modern amenities and a cozy layout. Whether exploring nearby galleries, museums, a day at the beach, or heading downtown - Bronzehaus offers a comforting stay. Come stay where heritage meets hospitality.

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!

Charming 2-bdrm near Obama Library/Hyde Park

Perfect for business travelers, healthcare professionals, and U of C affiliates, this newly renovated and fully furnished 2-bedroom, 1-bath apartment offers comfort and convenience. Located on a peaceful, tree-lined street in the vibrant Woodlawn/Hyde Park neighborhood, the unit features modern amenities including an in-unit washer and dryer, high-speed Wi-Fi, and a dedicated workspace. Public transportation (Metra + CTA) is just steps away and downtown Chicago in just 15 minutes by car.

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

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.

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 June 19, 2026) University of Chicago Hyde Park

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.

Beautifully Remodeled 2B in Historic Hyde Park

2nd-floor unit with two flights of stairs. Older building with radiant heat managed by the building. Enjoy your stay in this charming 2BR/1BA apartment in Hyde Park. Features a comfortable living area, full kitchen, and cozy bedrooms—perfect for families, friends, or business travelers. Close to the University of Chicago, Museum of Science and Industry, and lakefront parks. Easy access to dining, culture, and public transit. A great home base for exploring Chicago!

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Peaceful Hyde Park Studio Near UofChi & Nightlife

Stay in the heart of Hyde Park! This cozy 400 sq. ft. studio features a queen bed, 65" Roku TV, full kitchen, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. Easy access to Metra, CTA buses, and the lakefront make exploring Chicago simple and convenient. Perfect for solo travelers, couples, or weekend getaways seeking comfort and style in a vibrant, historic neighborhood.