Vacation rentals with a patio in Wicker Park

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in Wicker Park

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite
A modern living area is shown featuring a light-colored sectional sofa and a wall-mounted television. Natural light enters through large windows, and a small indoor plant adds a touch of greenery. A low coffee table sits in front of the seating area, enhancing the inviting atmosphere.
Apartment in Noble Square
4.97 out of 5 average rating, 108 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.

Top guest favourite
A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.
Apartment in Roscoe Village
4.95 out of 5 average rating, 223 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Top guest favourite
A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.
Apartment in Lincoln Park
4.99 out of 5 average rating, 143 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Top guest favourite
A cozy living room features a gray sectional sofa and a teal accent chair, complemented by patterned curtains. A TV is positioned on a low stand, with framed artwork on the walls. Natural light filters through multiple windows, enhancing the vibrant decor.
Apartment in Wicker Park
4.98 out of 5 average rating, 124 reviews

Colorful Bucktown Garden 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.

Top guest favourite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park
4.97 out of 5 average rating, 133 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Top guest favourite
A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.
Condo in Wicker Park
4.94 out of 5 average rating, 184 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, 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)

Guest favourite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in West Town
4.96 out of 5 average rating, 165 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Guest favourite
The living area features an orange sofa paired with black chairs and a dining table, creating a modern and welcoming space. Natural light filters through the sheer curtains, illuminating the hardwood floors and a stylish area rug that enhances the contemporary decor.
Apartment in Noble Square
4.91 out of 5 average rating, 99 reviews

Pristine Chicago Home | 3BD |2BA |Free Parking (2)

Free Parking!! Step into luxury in this modern loft with 3 bedrooms, and 2 bathrooms & experience the feeling of being at home in a bright and spacious haven amidst the bustling city. This sophisticated loft is situated at the heart of Chicago's most iconic landmarks. 7-minutes drive to Downtown attractions. Relax in this neat loft and get a taste of authentic Chicago living. Take advantage of all the city has to offer, creating memories that last a lifetime! 1 king bed 2 queen beds

Guest favourite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in West Town
4.98 out of 5 average rating, 190 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Top guest favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.97 out of 5 average rating, 272 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).

Top guest favourite
A welcoming living area features a leather sofa paired with a decorative throw, complemented by a glass coffee table atop a patterned area rug. Natural light filters through the bright windows, illuminating the bookshelf filled with various books and houseplants adorning the space.
Apartment in Humboldt Park
4.98 out of 5 average rating, 120 reviews

Stylish Retreat – 2 min to Transit, Fast WiFi

Modern 2-bedroom apartment in vibrant Humboldt Park/West Bucktown, steps to public transit and top restaurant hot spots. Neighboring Wicker Park and Logan Square—two of Chicago’s trendiest areas. One block from Humboldt Park with walking trails, lagoon, and nature paths. Walkable location with public transport, cafés, shops, and groceries nearby. Fast WiFi, smart TV's, luxury bed linens, and a fully equipped kitchen, perfect for work or play.

Top guest favourite
The living area features a plush, gray sofa paired with a deep blue accent chair. A light-colored coffee table rests on a patterned rug, while warm lighting is provided by wall-mounted fixtures. A small bookshelf and decorative items add a personal touch to the space.
Condo in Wicker Park
4.84 out of 5 average rating, 372 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Popular amenities for Wicker Park accommodations with an outdoor patio

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Quick stats about vacation rentals with a patio in Wicker Park

  • Total vacation rentals

    Explore 120 vacation rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 8,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    120 of Wicker Park vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wicker Park rentals

  • 4.9 Average rating

    Wicker Park stays are highly rated by guests—averaging 4.9 out of 5!

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