Vacation rentals in Jackson Park, Chicago

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Top-rated vacation rentals in Jackson Park, Chicago

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Guest favourite

Guesthouse in Hyde Park

4.94 out of 5 average rating, 82 reviews

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.

Condo in South Shore

4.6 out of 5 average rating, 5 reviews

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

Guest favourite

Vacation home in South Shore

4.94 out of 5 average rating, 80 reviews

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

Guest favourite

Condo in Woodlawn

4.96 out of 5 average rating, 46 reviews

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!

Guest favourite

Apartment in Woodlawn

5 out of 5 average rating, 11 reviews

Charming 2-bdrm near University of CHI Campus

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.

Guest favourite

Townhouse in South Shore

4.95 out of 5 average rating, 19 reviews

Gated 3-Level Apt, Near Hospitals and Downtown

This modern 3-bedroom, 1.5-bathroom South Shore retreat spans three levels, is travel friendly and well equipped for a comfortable stay in Chicago. Situated in the highly desirable historic Jackson Park Highlands neighborhood, this home provides convenient access to local/national attractions and public transportation. This townhouse strikes the perfect balance of comfort, convenience, affordability and location - making this an excellent option for your next stay in sweet home Chicago!

Guest favourite

Apartment in Hyde Park

4.93 out of 5 average rating, 119 reviews

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. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Top guest favourite

Apartment in South Shore

4.94 out of 5 average rating, 18 reviews

Comfy 3Bdrm near LSD,Obama Center, UIC, Sci Museum

South Shore located along Chicago’s shoreline, with stunning views of Lake Michigan. This location is a perfect stay. Guest will enjoy easy access to everything from this centrally located apartment. Minutes to University of Chicago or nearby beaches. One block from Metra Train Station to downtown or the north suburbs. Less than a mile from Obama Library or the Science Museum. Or travel the Nearby Lakeshore drive to downtown in just 15 minutes. Jewel Osco grocery located nearby.

Superhost

Apartment in South Shore

4.77 out of 5 average rating, 39 reviews

South Shore Oasis

Discover South Shore's charm in this renovated 1-bed basement apt within the owner's home, perfect for UChicago visitors—parents, graduates, and professionals. Though outside Hyde Park, it's just a 5-min walk to transit, offering quick access to campus and downtown. Enjoy the lakefront, bike trail, and beach nearby. Separate entrance ensures privacy, with the owner on-site for local tips. Experience tranquility with easy access to excitement. Book now for memorable stays!

Loft in South Shore

4.83 out of 5 average rating, 29 reviews

Historical Basement by Jackson Park; Metra/Parking

Stay in our historical XIX Century home in Chicago's iconic African American district! Imagine living like locals in this up-and-coming neighborhood. Enjoy: • Proximity to Hyde Park, Lake Shore Drive, Starbucks, market, laundromat, fast food • Steps to Jackson Park Hospital • 22-min Metra train ride to downtown • 15-min drive downtown • Close to Obama Presidential Center, Museum of Science & Industry, Jackson Park Highlands & Golf Course • Free designated parking

Guest favourite

Apartment in Hyde Park

4.83 out of 5 average rating, 6 reviews

Peaceful Hyde Park Studio; Near UChicago & Lake

Welcome to our cozy Hyde Park studio, perfect for 2 guests! Just minutes from the University of Chicago and the beautiful lakefront, this space offers comfort and convenience in one of Chicago’s most historic neighborhoods. Explore the vibrant 53rd St strip filled with cafes, shops, and local charm. Whether you're here for study, leisure, or a bit of both, enjoy a peaceful stay in the heart of Hyde Park.

Guest favourite

Condo in Woodlawn

4.95 out of 5 average rating, 56 reviews

The Modern Woodlawn 2 Bed 2 Bath

Enjoy a stylish experience at this centrally-located place. Minutes from University of Chicago, the upcoming Obama Presidential Library, Golfing at the South Shore Country Club, Lake Michigan, Public Transportation and Downtown Chicago. There is an ALDI grocery store around the corner. Jewels Grocery Store is a few minutes drive by car. Free Street Parking.