House holiday rentals in Wicker Park

4.98 out of 5 average rating, 162 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Unwind on the private rooftop deck, soak in the luxurious jacuzzi tub or take a relaxing steam shower after you host a dinner party in your own spacious dining room. Then watch a movie in the entertainment center with popcorn machine and 75 inch TV. Bedrooms are as follows: Master - king 2nd - twin and crib 3rd- queen 4th - twin over full bunk 5th - king and twin over twin bunk We also have a large, U shaped, 40 inch deep Cloud sectional from RH that can sleep 2-3 and 2 air mattresses. Stunning newly renovated home in a fantastic Wicker Park Location! Wicker Park is the Brooklyn of Chicago with tons of unique shops, restaurants full of character and innovative bars. The entire home is yours, giving you rarely found complete privacy in the middle of the city for you, your family, friends and colleagues to enjoy! Expertly designed with gourmet kitchen and multiple living rooms, your party will have plenty of room to spread out during your stay in the Windy City. Utilizing the finest materials & craftsmanship available, some of the premium features include: hardwood flooring on entire 1st and 2nd levels, 10' ceilings, beautiful moldings, sensational gourmet kitchen with large center island, premium stainless appliances and quartz counters, extra-large bedrooms including luxurious master suite with lavish marble baths, steam shower and expansive walk-in closet. Five full bedrooms and 4 bathrooms. The master bedroom has a King bed and very large ensuite bathroom. Bedroom 2 has a twin bed and a crib (upon request), bedroom 3 has a queen bed and a daybed. Bedrooms 2 and 3 share a hall bath. Bedroom 4 has bunk beds and bedroom 5 has a king bed and a daybed. Bedrooms 4 and 5 share a bathroom. The basement has a large entertainment area with a wine fridge, popcorn machine and 75 inch TV. **For those with infants and toddlers, in addition to a crib, we also have a SNOO bassinet and a Bugaboo cameleon stroller for your use. **If you would like to use any of these, please specify in your booking so that we can have them out and available to you. Otherwise, we keep them out of the way for guests who are not needing them. If you need parking please let me know in advance ** We have keyless entry for super easy check in. I am always available by phone, texting is best, but we want you to have the most convenience possible. That’s why we have keyless entry for seamless check in. No hassle for late arrivals, etc. Simply type in the code provided after confirmation and you’re all set! The neighborhood is the most buzzed about in Chicago, with trendy restaurants, shops, and bars within an easy walk, not to mention the beautiful park. Blue line is only a few blocks, which gives direct access to O'Hare International Airport. Uber and Lyft are always minutes away, and a Divvy bike station is right around the block. Chicago is a great city to explore. We are in the living breathing heart where locals reside so you’ll get the best the city has to offer!

4.92 out of 5 average rating, 287 reviews

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.

4.98 out of 5 average rating, 111 reviews

Home in Lincoln Park

Flat in Lincoln Park 2-Flat Central to Everything

Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

4.96 out of 5 average rating, 180 reviews

Home in North Park

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.97 out of 5 average rating, 115 reviews

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

4.93 out of 5 average rating, 160 reviews

Home in Avondale

BoHo House - A Chic, 1903 Chicago Workers Cottage

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee and snacks, and secure 2-car garage parking!

4.98 out of 5 average rating, 160 reviews

Home in Berwyn

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

4.95 out of 5 average rating, 100 reviews

Home in Logan Square

City Cottage in Logan Square-Avondale

Our two-bedroom home has been beautifully appointed for a relaxing stay. You'll have access to all the amenities of home with a private backyard space. The location is conveniently located between Avondale and Logan Square neighborhoods. It's a 14-minute walk to either the Belmont Blue Line or Logan Square Blue Line stops that take you to Downtown or O'Hare Airport. Walk to great restaurants, coffee shops, bars, music venues, vintage boutiques, Logan Square Farmers Market, and more!

4.91 out of 5 average rating, 126 reviews

Home in Logan Square

Kid friendly 2 bedroom w/ private office

Come enjoy a hip trip to Logan Square, Chicago! Minutes from local bars, restaurants, parks, the bike trail, and public transit, our toddler friendly, 2 bedroom 1st floor apartment has all you need! Cozy bedrooms and brightly lit common spaces make our space inviting and relaxing. Enjoy a private dedicated work from home space with large windows and tons of light. A front porch swing is also great for a morning cup of coffee or adult beverage wind down. We can't wait to host you!

4.97 out of 5 average rating, 260 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).

4.98 out of 5 average rating, 126 reviews

Home in Humboldt Park

Charming single-family home for 6! FREE Parking!

*NOTE: Updated April 2024 to include our whole house. Previous reviews were from our basement studio that hosts now occupy. **Our calendar is open for Thurs-Sun stays; inquire for longer stays/different dates. Just steps from the 606 elevated trail giving you access to some of Humboldt Park, Logan Square, and Wicker Park’s hottest restaurants, bars, and attractions. Perfect for families, couples, or groups of 6.