Vacation rentals in Jackson Park, Chicago

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Top-rated vacation rentals in Jackson Park, Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A private courtyard is showcased, featuring a combination of seating arrangements including a sectional sofa and a circular table with chairs. Surrounding greenery adds a natural touch, while the two-story guest house stands in the background, offering a comfortable outdoor space for relaxation.
Guesthouse in Hyde Park
4.94 out of 5 average rating, 87 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.

Superhost
The living area features hardwood flooring and blue upholstered sofas with cushions. A light, modern coffee table sits in front of the seating area. The space is illuminated by natural light through nearby windows, enhancing its airy feel.
Condo in South Shore
4.83 out of 5 average rating, 12 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 favorite
The living room features a comfortable gray sofa and a wooden coffee table set on a soft area rug. A Smart HDTV is positioned against a wall, while natural light enters through a large window adorned with light curtains. Decorative lighting fixtures enhance the space.
Vacation home in Jackson Park Highlands
4.94 out of 5 average rating, 82 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

Superhost
An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.
Condo in Woodlawn
4.92 out of 5 average rating, 50 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 favorite
Private room in Hyde Park
4.95 out of 5 average rating, 133 reviews

Top location, sunny UofC Prof on campus home

NO closer accommodation to the U of c campus, large wrap around deck with garden and small semi private deck. convenient access to lakefront, Obama house, Science and Industry museum, public transport. Excellent do it yourself morning breakfast in large kitchen, sparkling clean home. Newly renovated room, marble bathroom floors. More like a traditional bed and breakfast than airbnb. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Guest favorite
A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.
Apartment in Hyde Park
4.93 out of 5 average rating, 125 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. 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.

Top guest favorite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in South Side
4.99 out of 5 average rating, 126 reviews

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.

Guest favorite
A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.
Private room in Hyde Park
4.92 out of 5 average rating, 285 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Guest favorite
Apartment in South Shore
4.75 out of 5 average rating, 8 reviews

Lakeside Chic: An Urban Oasis

Welcome to 7424 S. South Shore Drive Unit 110 Airbnb! Nestled in Chicago's historic South Shore, this cozy retreat is steps from Lake Michigan's shoreline. Explore the nearby South Shore Cultural Center for arts, stroll through Jackson Park, and savor diverse dining options. With easy access to downtown attractions, this location offers the perfect blend of relaxation and urban exploration. Your ideal Chicago getaway starts here!

Superhost
A modern bedroom features a plush, spacious bed with a tufted teal headboard. Decorative pillows add a subtle pop of color, while a sleek bedside lamp sits on a wooden nightstand. Neutral walls enhance the serene ambiance of the room.
Hotel room in Grant Park
4.78 out of 5 average rating, 405 reviews

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Guest favorite
The kitchen features wooden cabinetry, stainless steel appliances, and a variety of countertop equipment. A small mat lies on the floor, and a step stool is positioned near the fridge. Natural light enters through a window, complemented by potted plants on the countertop.
Private room in Woodlawn
4.93 out of 5 average rating, 164 reviews

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)

Top guest favorite
A welcoming living room features a large wooden table surrounded by plants and comfortable seating. Natural light floods the space through expansive windows, enhancing the earthy tones of the decor. A cozy sofa and a vintage armchair create an inviting atmosphere for relaxation.
Private room in Hyde Park
4.96 out of 5 average rating, 520 reviews

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.

Popular amenities for Jackson Park, Chicago vacation rentals

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  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Jackson Park