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Vacation rentals with a patio in Woodlawn, Chicago

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Top-rated patio rentals in Woodlawn, Chicago

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Apartment in Chicago

4.9 out of 5 average rating, 62 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!

Jan 27 – Feb 3

€ 149 per night

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.

Sep 21 – 28

€ 97 per night

Guesthouse in Chicago

5.0 out of 5 average rating, 34 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

€ 394 per night

Home in Chicago

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.

Nov 13 – 20

€ 331 per night

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!

Mar 30 – Apr 6

€ 220 per night

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.

Apr 19 – 26

€ 216 per night

Home in Chicago

4.91 out of 5 average rating, 87 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.

Jan 9 – 16

€ 143 per night

Apartment in Chicago

4.87 out of 5 average rating, 45 reviews

Chateau de Woodlawn Peaceful 3 bedroom apartment.

Keep it simple at this peaceful and centrally-located 3 bedroom apartment. We offer comfortable seating and beds in the living room, dining room, and bedrooms. Use the full service kitchen to prepare your favorite meals. A private office space is available or relax on the patio with a meal, a book, or a nap. Within 10 mins from Washington Park nature path, 2 miles of the lakefront beach, 5 mins drive from the Hyde Park shopping and restaurant district and University of Chicago.

Nov 3 – 10

€ 167 per night

Apartment in Chicago

4.83 out of 5 average rating, 209 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Jan 10 – 17

€ 135 per night

Condo in Woodlawn

4.94 out of 5 average rating, 32 reviews

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.

Jan 27 – Feb 3

€ 234 per night

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.

Jan 31 – Feb 7

€ 226 per night

Apartment in Cicero

4.98 out of 5 average rating, 201 reviews

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

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Dec 11 – 18

€ 135 per night

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Popular amenities for Woodlawn, Chicago patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in West Town

4.93 out of 5 average rating, 184 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

Feb 16 – 23

€ 213 per night

Apartment in Oak Park

4.91 out of 5 average rating, 103 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Aug 24 – 31

€ 171 per night

Apartment in Berwyn

4.87 out of 5 average rating, 137 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Jul 9 – 16

€ 111 per night

Apartment in Forest Park

4.85 out of 5 average rating, 110 reviews

Home away from home downstairs

Aug 24 – 31

€ 126 per night

Apartment in Chatham

4.92 out of 5 average rating, 12 reviews

Your Oasis of Elegance in Greater Grand Crossing

Jul 11 – 18

€ 122 per night

Apartment in Chicago

4.89 out of 5 average rating, 9 reviews

Beverly Cottage Loft

Jul 23 – 30

€ 148 per night

Apartment in Chicago

4.88 out of 5 average rating, 34 reviews

Bronzeville/ UofC Greystone Free parking, wifi

Oct 26 – Nov 2

€ 145 per night

Apartment in Chicago

5.0 out of 5 average rating, 19 reviews

The Dearborn Suite 2

Jul 17 – 24

€ 271 per night

House rentals with a patio

Home in Chicago

4.96 out of 5 average rating, 200 reviews

Division St Designer Home In Heart of Wicker Park

May 20 – 25

€ 329 per night

Home in Chicago

4.95 out of 5 average rating, 19 reviews

Spacius unit in historic gem

Aug 21 – 28

€ 201 per night

Home in Woodlawn

4.88 out of 5 average rating, 42 reviews

Cozy Chicago House near Hyde Park!

Apr 4 – 11

€ 346 per night

Home in Hyde Park

5.0 out of 5 average rating, 13 reviews

Modern Family Townhouse

Dec 26 – Jan 2

€ 379 per night

Home in Chicago

4.91 out of 5 average rating, 43 reviews

Cozy Bright Quiet Boho-Chic House in Bridgeport

Mar 21 – 28

€ 161 per night

Home in Chicago Ridge

4.9 out of 5 average rating, 50 reviews

Quiet cul-de-sac with huge fenced in backyard

Nov 24 – Dec 1

€ 159 per night

Home in Chicago

4.93 out of 5 average rating, 70 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Nov 8 – 15

€ 415 per night

Home in South Chicago

5.0 out of 5 average rating, 41 reviews

Spacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens

Apr 4 – 11

€ 575 per night

Condo rentals with a patio

Condo in Chicago

4.96 out of 5 average rating, 118 reviews

Private hot tub - King bed suite - Free parking

Jun 7 – 14

€ 382 per night

Condo in Chicago

4.98 out of 5 average rating, 102 reviews

Interior designer duplex 2bd 2bath w/ prvt office

Apr 16 – 23

€ 370 per night

Condo in Chicago

4.96 out of 5 average rating, 99 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Sep 19 – 26

€ 367 per night

Condo in Chicago

4.95 out of 5 average rating, 128 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Jan 11 – 18

€ 780 per night

Condo in Chicago

4.95 out of 5 average rating, 110 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Jun 15 – 22

€ 488 per night

Condo in Wrigleyville

4.82 out of 5 average rating, 176 reviews

Can't Beat This 2min Walk to Wrigley!

Mar 11 – 18

€ 518 per night

Condo in Chicago

4.82 out of 5 average rating, 187 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Jul 8 – 15

€ 945 per night

Condo in Wicker Park

4.82 out of 5 average rating, 309 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Aug 24 – 31

€ 339 per night

Quick stats about vacation rentals with a patio in Woodlawn, Chicago

Total rentals
90 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
€ 19 before taxes and fees

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