
Vacation rentals with outdoor seating in Wicker Park
Find and book unique outdoor seating rentals on Airbnb
Quick stats about vacation rentals with outdoor seating in Wicker Park

Total vacation rentals
Explore 70 vacation rentals in Wicker Park

Nightly prices starting at
Wicker Park vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 6,620 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
70 of Wicker Park vacation rentals include wi-fi 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!
Top-rated outdoor seating rentals in Wicker Park
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Cool Quiet Coach House, Private Access + Patio
Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Modern LOFT Ukrainian Village 2nd floor
Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue

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.

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.

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking
Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! 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! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

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.

Ukrainian Village Garden Retreat | Free Parking
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.

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.

Stylish 2-bedroom flat in Vibrant Bucktown.
* Please be aware the city of Chicago is currently renovating its lead pipes. Construction is inevitable and noise. Its a city there will be noise. Hello and welcome to Bucktown! One of Chicago's most popular neighborhoods. Bucktown is centrally located, just a short commute to downtown and surrounded by the best dining and entertainment options Chicago has to offer. We are also half a mile from the expressway and 1 mile away from the Blue Line which directly connects to O'hare airport.

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.

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.

𓃥Wicker Cozy Corner w/Parking on site
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. 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.
Popular amenities for Wicker Park outdoor seating rentals
House rentals with outdoor seating

City Cottage in Logan Square-Avondale

Entire 3 BR+2 office areas & deck, top floor condo

NEW! 3BR/2.5B Duplex in Noble Sq

Flat in Lincoln Park 2-Flat Central to Everything

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

BoHo House | Chic, 1903 Chicago Workers Cottage

Vintage Designed 3BR Condo Near DePaul University

3 bed/2 bath by United Center w/ private parking
Apartment rentals with outdoor seating

Wicker Park Walk-Up Condo

A Vintage Pink House in the Heart of Chicago

iKlektik House Chicago/BlueJay

Hip Chicago Condo in fun shopping and dining area

Decompress on a Sophisticated Chaise at a Glamorous Hideaway

Stylish 2BR stunner w/ unbeatable location

Wicker Park Historic, Art-Filled, Urban Oasis #2

Sun filled tranquil 2 br great part of Logan Sq.
Condo rentals with outdoor seating

Luxuriously bright 6-bedroom duplex: The Treehouse

Inspired, luxe living in Logan Square on BLVD #1

Logan Square Beauty with 2 Bedrooms W/parking

Chicago Oasis | Spa Bath, Patio & Fireplace

Your Chicago Retreat

Susie's Space. 2BR easy parking & pet friendly

Wrigleyville Updated Condo with Free Parking

Spacious 4 Bedroom Condo
Destinations to explore
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- Rentals with outdoor seating Chicago
- Rentals with outdoor seating Cook County
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- Rentals with outdoor seating United States
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort
- Washington Park Zoo





