Vacation rentals with outdoor seating in Wicker Park, Chicago

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Top-rated outdoor seating rentals in Wicker Park, Chicago

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Superhost

A spacious living area features large sliding glass doors that open to a balcony, allowing natural light to fill the room. Two dark blue bean bags and a glass coffee table are positioned in front of a white sofa, creating a relaxed seating arrangement.

Apartment in Wicker Park

4.94 out of 5 average rating, 144 reviews

Spacious Studio w/Balcony in Bucktown/Wicker Park

My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.

Superhost

The historic brick building features a distinctive green turret and a mix of large windows. The façade showcases intricate architectural details that contribute to the character of the property, with a welcoming entrance and a well-maintained exterior.

Apartment in Wicker Park

4.78 out of 5 average rating, 291 reviews

Private Studio Apt in the Heart of Wicker Park!

*No Hidden Cleaning Fees or Deposits* Enjoy Wicker Park with your own private renovated studio apartment! The apartment comes complete with a large living space, including a twin day bed which can be pulled out and converted into a king size bed. The kitchenette has a fridge & microwave. There is A/C, fast WiFi, TV, new bathroom, laundry facilities and a communal rooftop deck with skyline views. Close to EL train, highway, shopping, restaurants, nightlife, cafes, 606 bike trail and more!

Superhost

The living area features a sleek television mounted on the wall, complemented by a stylish wooden cabinet. A light-colored sofa is positioned in front of a rectangular coffee table, with a decorative bowl resting on it. The space is enhanced by natural light from the windows and greenery.

Apartment in Wicker Park

4.93 out of 5 average rating, 332 reviews

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

Superhost

A vibrant living area features two orange armchairs positioned around a decorative wooden table. A floral wallpaper adorns the wall behind a wall-mounted television, while a rich area rug anchors the space. Natural light filters through sheer curtains, highlighting the room's colors.

Apartment in Wicker Park

4.96 out of 5 average rating, 156 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.

Superhost

A cozy seating area features a round table surrounded by two chairs. A potted plant is positioned nearby, contributing to the fresh atmosphere. A glass coffee table rests on a patterned rug, while a comfortable gray sofa with assorted cushions is present against the wall.

Apartment in Wicker Park

4.98 out of 5 average rating, 287 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Superhost

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, 104 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.

Superhost

A charming brick two-story home is framed by lush greenery and colorful flower beds. The entrance is adorned with light fixtures, and steps lead up to a welcoming porch. The well-maintained garden features a variety of blooming plants, enhancing the inviting ambiance.

Guest suite in Bucktown

4.93 out of 5 average rating, 381 reviews

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed cozy suite with private keyed courtyard entry & small lighted covered patio w/table and chairs (work outside!) New ensuite bathroom w/heated floor, bespoke vanity & fab water pressure. Quiet tree-lined street with free parking, great restaurants, old pubs, shops & transport walkable. Great launch to all Chicago has to offer while enjoying charming Bucktown. Close to Downtown, DePaul, Zoo, Lincoln Pk, Wrigley, United Ctr, Lakefront.

Superhost

An open-concept living and dining area is highlighted by vaulted ceilings and large windows, allowing natural light to fill the space. A comfortable sectional sofa faces a round coffee table, while a wooden dining table with several chairs sits nearby. Decorative accents include artwork and plants.

Vacation home in Wicker Park

4.88 out of 5 average rating, 101 reviews

Penthouse. Historic Wicker Park. Walk | Shop | Eat

Urban Oasis. New Wicker Park Oasis Collection Launched. Brand new furnishings, beds and Decor in this prime Wicker Park location. Enjoy our intimate home with unparalleled access just steps to restaurants, boutique shops, bars & nightlife-one of Chicago's artistic & creative neighborhoods. Blue Line Train runs direct from O'Hare Airport to Downtown, Damen Stop 3 blocks away. Ambient city & train noise is to be expected in and around our home. Reserved Parking available. 1 Dog $35/night.

Superhost

A spacious dining area features a large wooden table surrounded by two long benches. Artwork is displayed on the light gray walls, and natural light floods in from a large window. A small desk and chair are positioned in the corner, adding functionality to the space.

Apartment in Wicker Park

4.88 out of 5 average rating, 169 reviews

Charming Two Bedroom in Wicker Park

Our apartment is on a quiet street in a trendy neighborhood that always has something cool going on. Wicker Park is a hive of activity that draws shoppers hunting for unique finds, foodies looking for the trendiest eats, and bar hoppers searching for late-night buzz. Ideal for couples, solo travelers, business travelers, and small groups looking for a central, comfortable spot. COVID note: We are taking an extra effort to disinfect and sanitize all surfaces during each cleaning.

Superhost

A bright living area features a spacious white sofa, a round wooden coffee table, and a cozy armchair. A circular area rug adds texture to the floor. Natural light enters through large windows, illuminating the room's neutral decor. A dining table is partially visible in the background.

Apartment in Bucktown

4.95 out of 5 average rating, 132 reviews

BRAND NEW Elegant Renovation in Bucktown (Chicago)

Elegant, newly renovated 1 bedroom apartment nestled in the trendy Chicago neighborhood of Bucktown. Our home is the perfect place for you to stay while you explore the city. Located just a few blocks away from vibrant Bucktown restaurants, live music, bars, 606 city trail, and downtown. The Damen blue line subway station is about 10 minute walk from the apartment, giving guests easy access to O’Hare and the rest of the city. Free street parking is also available.

Superhost

A cozy living space is presented, featuring a dark leather couch adorned with accent pillows. A coffee table with a colorful top complements a simple dining setup with two chairs. Framed art pieces decorate the walls, and natural light flows through the nearby window.

Apartment in Wicker Park

4.97 out of 5 average rating, 157 reviews

Cozy Urban Getaway East Village Apartment

Cute, airy space ideal for singles or couples traveling to Chicago as digital nomads or an extended stay! Walkable to hip eateries/tacorias/ bars, yummy coffee shops, boutique grocery stores, open parks--and less than a mile from the Blue Line--which can take you to O'Hare Airport or downtown. Designer kitchen ready for you! Living room features comfy couch and local artists' work. Guests report this is one of the best showers they've experienced!

Superhost

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

Apartment in Wicker Park

4.95 out of 5 average rating, 127 reviews

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.