Vacation rentals with outdoor seating in Wrigleyville, Chicago

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Top-rated outdoor seating rentals in Wrigleyville, Chicago

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Guest favorite

A cozy sleeping area features a neatly made bed with soft gray pillows and a decorative green bolster. A bedside lamp and a small plant add touches of comfort, while a piece of framed artwork hangs on the white wall above the bed.

Guest suite in Pilsen Historic District

4.99 out of 5 average rating, 118 reviews

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

Superhost

A covered outdoor seating area features two colorful chairs, one turquoise and one green, positioned around a small side table. The entrance door is partially visible, framed by wooden posts and illuminated by natural light.

Apartment in West Town

4.86 out of 5 average rating, 400 reviews

Explore the City from an Elegant, Urban Retreat

- Queen Size bed in the private bedroom for two guests. - Sofa Bed with Full Size mattress for the 3rd and 4th guests (light weight and easy to setup). - Additional portable twin size cot can be set up per request. - Private Bathroom has a ceiling speaker and night light. - Living Room has an HD cinema projector with 100" screen. - A private garden with a gas grill and patio dining table/chairs. - Entry gate and door are Keyless/ Secured Key-coded. - Attached Private Parking space is available per request (subject to availability). - Easy Street Parking: Street parking is zoned (Chicago Residential Zone Parking) and we provide daily zone permits for parking on the street in front of the apartment. - Garden Space offers gas grill for Summer/Fall cookout (Share with two other apartments in the building). Text or phone call for quick reply The apartment is near the popular West Loop and West Town neighborhoods and close to public transit. Downtown parks, museums, and shops are less than two miles away. There's a Divvy Bikes station and a Starbucks across the street. Short walk to public transit ("L", bus, or Divvy bikes) 1 min drive to I-90/94. Less than 2 miles to downtown parks, museums, and shopping destinations. Less than 10 min drive to Lincoln Park, Old Town, and 5 min drive to Wicker Park, and Bucktown.

Guest favorite

A shared backyard features a vibrant Japanese maple tree alongside lush greenery and flowering plants. A wooden deck is seen above, with stairs leading up. A pergola with a grill is positioned to the right, creating a welcoming outdoor space.

Apartment in Ukrainian Village

4.92 out of 5 average rating, 191 reviews

iKlektik House Chicago / BlueJay

Enjoy the warm heated floors and check out this home's amazing craftsmanship and artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM The apartment is located in West Town. CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

Superhost

A tranquil seating area features two lounge style couches and a low glass table made from natural wood. Soft neutral tones dominate the space, complemented by natural light filtering through sheer curtains. Decorative elements, such as a potted plant and wall mirrors, add subtle interest.

Apartment in Chicago

4.84 out of 5 average rating, 279 reviews

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

Guest favorite

A private patio features two wicker chairs and a small black table, surrounded by a wooden railing. The view showcases the rooftops of neighboring buildings, with a clear blue sky in the background and the Chicago skyline faintly visible.

Apartment in Wicker Park

4.96 out of 5 average rating, 144 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.

Guest favorite

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, 147 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)

Top guest favorite

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 West Town

4.97 out of 5 average rating, 149 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!

Guest favorite

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Guest favorite

An inviting outdoor space is captured, featuring a black and white patterned couch adorned with bright yellow pillows. A pink coffee table stands prominently on a patterned rug, surrounded by potted plants, creating a vibrant atmosphere. The area is bordered by exposed brick walls.

Home in Wicker Park

4.9 out of 5 average rating, 200 reviews

Tropical Penthouse in Wicker Park w/Backyard Patio

Find us on Insta @bangtel Named "Top 10 Luxury Properties in Chicago" by Time Out. Need a tropical escape? Just add water, a flamingo, and a palm tree to this luxe escape in the heart of Wicker Park. We have plenty of sleeping arrangements for 14 guests. Need more room? Check out ALOHA 2.0 that sleeps 23 guests. Follow us on IG @bangtel —link in IG BIO! *NEW listing link - airbnb.com/h/aloha-bangtel

Superhost

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

Guest favorite

The exterior view of the custom Prairie-inspired home is presented, featuring a stone facade and wooden accents. Turquoise doors serve as the entrance, flanked by light fixtures. Lush greenery surrounds the pathway leading to the front, while blooming trees and shrubs enhance the serene setting.

Home in Justice

4.93 out of 5 average rating, 224 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

3 Kings | 1 Queen | 1 Full | 3 air beds | 2 Pack 'n Plays No charge for: cleaning, extra people, or any other hidden fees. 20% weekly discount applied to 7+ nights. 20% monthly discount. Less than 5 mins to I-294, I-55. 30 mins to Chicago & O'Hare Airport. 15 mins to Midway Airport. 5 mins to Cook County’s forest preserves w/ bike, walking, and horse trails.

Guest favorite

A two-story coachhouse features a yellow exterior with white railings along a spacious porch. A stairway leads up to the porch from the ground level, and a single door is visible at the base of the steps. Surrounding trees are bare, indicating winter.

Guesthouse in Oak Park

4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!