Vacation rentals with a patio in Woodlawn, Chicago

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Top-rated patio rentals in Woodlawn, Chicago

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Superhost

Apartment in Chicago

4.9 out of 5 average rating, 63 reviews

Eclipse: Apt. in Woodlawn | Near UChicago

Modern 2 bedroom basement apartment has a style of its own and is perfect for your stay in Chicago. It's a central location to explore Chicago w/ vehicle, ideal for working professionals & families visiting students and medical hospital. Driving: Located 6 min to University of Chicago, mins to lakefront and beach. 10 min to Hyde Park restaurants and attractions, 20 min downtown Chicago. Near expressways. Code entry for convenient check-in and free street parking. Please read entire listing!

Apr 9 – 16

G$27,389 GYD per night

Guest favorite

Guesthouse in Hyde Park

5.0 out of 5 average rating, 36 reviews

2 br, 2 bt, detached, UChicago Coachman's House

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.

Dec 29 – Jan 5

G$68,717 GYD per night

Superhost

Guest suite in Chicago

4.8 out of 5 average rating, 61 reviews

Comfortable and Cozy Suite in Quiet Neighborhood

Are you coming to town to visit family, friends or for business? This cozy, clean, comfortable & 420 friendly suite has all you need to escape your everyday. Look no further! This one-bedroom suite is perfect for 1-3 people, small families, or individuals. If you're visiting family or friends and want your personal space or are in town for business and need a comfy bed, wifi, and office space, then this place was designed for you. Kick back and relax in this calm, stylish, 420 friendly space.

Oct 22 – 29

G$14,443 GYD per night

Guest favorite

Home in Chicago

4.95 out of 5 average rating, 19 reviews

Spacius unit in historic gem

Bring the whole family to this great place with lots of room for fun. Two retro arcade games & an air hockey table to enjoy. Spacius apartment with room for everyone to relax comfortably. Super close to everything Chicago has to offer. 12 minutes to the heart of downtown. 5 minutes to the University of Chicago. 8 minutes to McCormick place, Soldier Field, Credit 1 Arena and Sox Stadium 10 mins to the beach/lake 15 mins to the United Center Walking distance to 2 train lines leading downtown

Nov 6 – 13

G$34,781 GYD per night

Superhost

Home in Woodlawn

4.82 out of 5 average rating, 96 reviews

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.

Jan 28 – Feb 4

G$53,650 GYD per night

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 15 reviews

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Remodeled unit with open floorplan, hardwd floors, stainless steel appliances, in-unit washer/dryer, and private parking space. Cozy reading nook and huge outdoor patio. Quiet treelined street, minutes from Hyde Park and within waking distance of Lake Michigan, Jackson Park Golf Course and the upcoming Obama Presidential Library and the 222,000-sq ft Regal Mile Film Studios. Welcome to your new home away from home!

Jul 12 – 19

G$34,760 GYD per night

Superhost

Apartment in Chicago

4.94 out of 5 average rating, 31 reviews

Lovely 3 bedroom rental unit with patio

This stylish 3 bedroom 1 bathroom is perfect for the entire family! The apartment offers comfortable sleeping accommodation's for 5 with 2 dedicated off street parking spaces available; free on-street parking is also available. You will have access to the entire 1st floor unit with patio, except for locked closets. 3 bedrooms have 1 Queen, 1 Full and 1 Twin Size, along with a living room couch (does not contain a sleeper). 3 mins to I-94 and walking distance to METRA commuter train station.

Jul 7 – 14

G$37,171 GYD per night

Guest favorite

Home in Chicago

4.91 out of 5 average rating, 88 reviews

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.

Mar 2 – 9

G$23,884 GYD per night

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 120 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Jun 25 – Jul 2

G$59,345 GYD per night

Superhost

Apartment in Lincoln Park

4.86 out of 5 average rating, 188 reviews

Perfect Lincoln Park Retreat - Walk to Depaul!

This perfectly located 2 BD/2 BA unit is waiting for you to call it home for your trip to gorgeous Lincoln Park! Make yourself comfortable in the sleek and modern interior of this newly renovated garden unit. Enjoy all of the comforts of home, as well as some cool features you don't see every day– such as LED-lit mirrors in both bathrooms! Walk to famous attractions like the historic Kingston Mines blues bar and the Lincoln Park Zoo, as well as the DePaul campus & 'El' train stop.

Jan 26 – Feb 2

G$30,689 GYD per night

Guest favorite

Apartment in Beverly

4.92 out of 5 average rating, 12 reviews

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Dec 12 – 19

G$24,948 GYD per night

Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 50 reviews

Washington Estate minutes from University of CHI

Kick back and relax in this calm, stylish space. The Washington Estate is the professional escape. We provide a 1-bed/2-bath to accommodate a maximum of two guests. Everything you need, full kitchen, WIFI, exercise room, in unit laundry and exterior patio seating for your enjoyment. Gated parking available upon request. Near the historic Hyde Park, the University of Chicago and 8 minutes away from Lake Shore Drive. Walking distance from public transportation.

Oct 1 – 8

G$36,586 GYD per night