Apartment holiday rentals in Woodlawn

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

Quaint Apt near UChicago, Wifi + Parking + Laundry

Unwind at our stylish and cozy 3-bedroom, 2-bathroom apartment located just steps from the University of Chicago in the vibrant Woodlawn neighborhood. The space features, an open-floor plan, hardwood floors, a fully equipped kitchen, plenty of natural light. It's the perfect place for a family or a group of friends who want a quiet place to relax while still being close to food, fun and tourism in Chicago. Ideal for family vacations, group trips, traveling professionals or students.

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.

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!

Private Duplex w/ Games + Theater | Near UChicago

Enjoy our spacious 2-level home this fall and winter, perfect for families and groups. The lower level is your entertainment hub with a 120" projector, retro arcade, ping pong, board games, reclining sectional, 1 bedroom, and 1 bath. Upstairs features two bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen with coffee, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all.

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

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.

Beautiful European Apartment

Enjoy this comfortable 1600 sf European Styled 3 bedroom (Queen Beds in each room) 1 bath apartment with lots of natural light. Formal dining room,comfortable living room with attached sunroom. Quite neighborhood and 3 blocks away from Public “Elevated Train” line and “Buses” to anywhere in Chicago. The apartment is walking distance from University of Chicago and the beautiful Washington Park. The park has wonderful Walking/Running Paths and Pool (Seasonal).

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Sleek Apt near U of Chicago!

Come stay at our inviting apartment, minutes from the University of Chicago and hospital! Ideal for families, students, scholars, and travelers. Sleeps 6 (1 twin memory foam floor mattresses and 1 pull out couch). Free street parking! Explore nearby: Museum of Science and Industry, Robie House, golf, lake, and Hyde Park's charming shops/eateries. Easy public transport to Downtown Chicago for city adventures!