Pet-friendly holiday rentals in Wicker Park

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!

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.

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.

Luxury Designer Penthouse Loft | Sleeps 20

Designer Penthouse in the heart of Wicker Park! Sleeps up to 20 people! Enjoy your own private loft in Chicago's hip and trendy Wicker Park-one of the city's centers nightlife, restaurants and cultural scene. This 4,500 square foot penthouse sits on an entire floor features 18 foot open vaulted ceilings, authentic loft feel, 4 bedrooms/3 bathrooms, and is perfect for families, professionals visiting the city on work trips, and everything in between. The cityscape views are truly unbeatable!

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.

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.

Clean, Bright Chicago Apt in Bucktown/Logan Square

The whole group will enjoy easy access to everything from this centrally located place. The Western Blue line stop that takes you to downtown Chicago is 2 blocks away. Downtown is a 15 minute ride away if you decide to rent a car. This is the only apartment in the building and sits right above the BEST Grilled Chicken restaurant in Chicago. The apartment is walking distance to many delicious restaurants and local coffee shops. You can find some of the best food in Chicago just steps away.

Private coach house near transit shops & nightlife

This newly renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

Strictly Commercial Storefront: Humboldt, Bucktown

Enjoy a private entrance to your street-level storefront apartment at the intersection of Bucktown, Wicker Park, Humboldt Park and Logan Square neighborhoods. Easy access to transport. Rest in comfort and check out the 606 elevated trail, Humboldt Park, restaurants, shopping, and nightlife. Well-outfitted apartment features exposed brick, unique lighting, and lofted bedroom. Anthropologist? Watch the street scene through one way glass. You can see out, but your subjects can't see in.

Sophisticated Twnhm in Prestigious S. Lincoln Park

Welcome to our awesome townhome, nestled in a peaceful residential neighborhood, offering both convenience and serenity. Located with easy access to public transportation, you can explore all that Chicago has to offer. There are multiple levels to this townhome with stairs. A bedroom and bathroom on the ground floor, kitchen and living/dinning room on the middle floor, and the master bedroom with master bathroom on the top floor. A mini roof top to enjoy Chicago nights as well.

Logan Square Video Game Loft

Treat yourself to a unique stay in this hip video game themed studio. Enjoy the comfort of this large, bright space—and the games and artwork on display—during your trip. Explore the happening neighborhood scene in the Logan/Bucktown/Wicker Park area via the 606 walking trail (right outside the door) or walk two blocks to the Blue Line el stop for easy access to downtown or the airport. *Please be sure to review the Other Things to Note section as well as our house rules.

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.