Vacation rentals in Jackson Park, Chicago

Bike the Lakefront from a Sleek Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

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.

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

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.

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

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.

Cozy Chicago House near Hyde Park and the Beach!

Relax with the whole family at this peaceful home. Enjoy one king Bed, 2 Queen beds, one full bed, 3 Twin beds, a futon and plenty of lounge space on the couches and recliners. There is a full bathroom on each floor equipped with soaps, and all the needed toiletries. Stainless steel kitchen appliances and an island bar are ideal for prepping meals etc. Enjoy the back patio + Gazebo for the warmer days. Our dining table can be used to play cards, Jenga etc. Welcome! Any questions, ask!

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.

Bright & Cozy Studio in the Heart of Hyde Park

Cozy, sunlit Hyde Park studio just blocks from UChicago. Enjoy a comfy queen bed, private bath, fast Wi-Fi, and a fully stocked kitchen with all essentials. Nestled on a quiet, tree-lined street in a safe, walkable neighborhood near cafés, restaurants, parks, and museums. Easy CTA and Metra access for downtown trips. Perfect for solo travelers, couples, and visiting academics seeking comfort, convenience, and a welcoming, homey atmosphere.

Hyde Park Haven | 2BR Retreat

Your cozy 2BR retreat in the heart of Chicago’s historic Hyde Park neighborhood. What You’ll Love: • 2 Comfortable Bedrooms – Each with a plush Queen bed for restful nights • Bathroom – Clean, modern • Fully Equipped Kitchen – Cook up a storm or enjoy takeout from local gems • Bright Living Space – Kick back, stream your favorites, or plan your next adventure • Wi-Fi + Smart TV – Stay connected or unwind with ease

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!

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.