Holiday rentals with a patio in Woodlawn, 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.

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

Experience comfort and convenience in our modern stylish home. With 3 spacious bedrooms, 2.5 bathrooms, an open concept kitchen, and a backyard patio, there's plenty of room to relax and unwind. Our home is conveniently located near the highway, shopping, and restaurants. 5 mins from the University of Chicago and the Beach.. 10-15 mins from Hyde Park and Downtown, Soldiers Field, and lots of other sights in Chicago. Perfect place to stay if you are coming with a group!! Book your stay now.

Woodlawn LUXE! Near University of Chicago

Enjoy this newly renovated LUXE 4 bedroom 1 bathroom condo that you and your guest will love on the entire second floor of a two flat building! All bedrooms have LG Smart TV'S! Located with a 5 minute drive to The University of Chicago, Hyde Park, The Cultural Center, The Dusable Museum, and will be walking distance to the new Obama Library. A 30 minute drive to Midway airport 1 hour to Ohare. Chicago’s downtown, McCormick Place, and museums 30 minute drive. Located 4 blocks to Greenline L'

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Private Logan Square Garden Apt

Welcome to our cozy West Logan Square/West Humboldt Park/Hermosa garden apartment! Perfect for tradeshow/business travelers, solo travelers, &couples. Enjoy a comfy queen-size bed, workspace, fast Wi-Fi, and huge Smart TV w Roku. Plenty of power outlets to keep your devices charged. Get ready in bathroom w/ ample counter space & large mirror. Cook in the well-equipped kitchen with full-sized appliances, spices/oil, microwave & coffee/tea bar. Note: Hosts occupy first floor of the home.

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!

Cozy 3 Bedroom Condo near University of Chicago

Come experience this newly renovated, reclaimed red brick 1895 colonial multi-family building. Located 5 mins from the University of Chicago (if walking 1 mile), a 3 block walk to the CTA Green Line 'L' Station heading toward downtown, 10 mins from Sox's Stadium, 5 mins from a grocery store, closely located to restaurants, historic museums & parks, and shopping in Hyde Park (7 mins), 18 mins from downtown Chicago, 25 mins from Midway Airport and 40 mins from O'Hare.

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.