Vacation rentals with a patio in Wicker Park, Chicago

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Top-rated patio rentals in Wicker Park, Chicago

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Guest favorite

Apartment in Chicago

4.84 out of 5 average rating, 58 reviews

Quiet Bucktown Suite Easy Parking

Quiet Bucktown Garden Apartment in A+ location. Don't be fooled by other listings right next to loud trains/bars. Private suite equipped with full bath, fridge, large couch, and queen-sized bed + free public laundry with soap provided. Walk in any direction to get to some of Chicago's best bars and restaurants or hop on the blueline subway 3 blocks away and zip downtown to explore some tourist attractions. Very easy, free street parking on the block. NO SMOKING/VAPING OR DRUG USE ON THE PROPERTY

Sep 14 – 21

R2,352 ZAR per night

Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 144 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #1

Entire 2 bedroom apartment in art-filled, Wicker Park building 5 min. Uber to downtown Chicago. Public transportation 3 blocks away. Restaurants, shops, parks, and nightlife within walking distance. Space includes -Brand new bathroom, walk in shower -1 bdrm w/ queen size bed - large closet -1 bdrm w/ single size bed, desk, shelf space -Pull out queen size couch bed -Fully equipped kitchen -AC -Personal back porch -Beautiful garden w/ outdoor furniture -1 parking space included + parking passes

Sep 3 – 10

R3,929 ZAR per night

Guest favorite

Townhouse in Wicker Park

5.0 out of 5 average rating, 17 reviews

𓃥Wicker Cozy Corner

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking and EV charging. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.

Nov 5 – 12

R4,430 ZAR per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 100 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Jul 25 – Aug 1

R4,878 ZAR per night

Guest favorite

Apartment in West Town

5.0 out of 5 average rating, 25 reviews

Wicker Park Walk-Up Condo

Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

Feb 5 – 12

R3,503 ZAR per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 18 reviews

Funky Logan Lair

This gem is located in West Logan in the heart of everything Logan has to offer. The space is the basement unit of an owner-occupied single-family home with private entrance. One bedroom unit with a queen-size bed and living room with connecting kitchenette & bathroom with stand-up shower. The space includes a full size washer and dryer. Located next to the 606 Trail. Private entrance, Easy access to CTA and Divvy Bike Rentals, Free Wi-Fi, Fridge, microwave, toaster & Nespresso(with pods)

Jan 9 – 16

R2,189 ZAR per night

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 49 reviews

Colorful Bucktown Apartment

Enjoy a stylish experience at this centrally-located apartment. Close to all of the neighborhood amenities including the 606 trail, shopping district, highly reviewed restaurants, blue line "el" train, neighborhood parks, and more. Walk to everything you need or jump on the blue line to get downtown quickly. Our colorful space is perfect for your city stay. Enjoy comfortable spaces including an oversized bedroom, cozy living room, fully appointed bathroom, dining area, and a kitchenette.

Sep 9 – 16

R3,284 ZAR per night

Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 110 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this prime, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Jun 15 – 22

R7,570 ZAR per night

Guest favorite

Apartment in Chicago

4.93 out of 5 average rating, 184 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

This charming 2 bedroom/1 bath garden apartment is located in Ukrainian Village, a friendly neighborhood on Chicago's near West side! Steps to the restaurants and bars on bustling Division Street, our home is located on a quiet residential side street, so you will have the best of both worlds. Drive to downtown in just 10 - 15 minutes! For any type of traveler, our home is the perfect oasis. Don't miss out, book today! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Feb 16 – 23

R3,138 ZAR per night

Guest favorite

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

R2,053 ZAR per night

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 200 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

May 20 – 25

R5,219 ZAR per night

Guest favorite

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

R2,314 ZAR per night