House holiday rentals in Wicker Park

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.

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Private Roofdeck! Location! Parking! Amazing home!

Large Bucktown home with plenty of space for the whole family! Your group will have the best stay in the perfect location to explore all that Chicago has to offer. Steps away from the 606 walking trail and one block from the Blue Line. This home is situated on a beautiful tree lined street with charming bungalows highlighting Bucktown architecture. The home offers 2 floors of living space with a large kitchen, dining room, living room and 3 bedrooms. Custom bath with w/d. Parking included!

Wicker Park : Stylish Comfort Meets Urban Ease

Welcome to our Wicker Park/West Town condo, a beautifully decorated haven in Chicago's most vibrant neighborhood. Perfect for groups, it sleeps 10 with options for up to 12. Just a 5-min commute to The Loop and a short walk to the L train, our location is unbeatable. Enjoy a fully stocked kitchen, luxurious bath essentials, and strong WiFi. Experience the city's best dining and nightlife, all within walking distance. Book for a blend of comfort and convenience in the heart of Chicago.

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

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).

Beautiful Modern, large, 4BR/4BA Private Home

Fantastic, spacious, light filled house in one of Chicago's coolest neighborhoods. Four large bedrooms, two that are full master suites. Huge kitchen with open floor plan to dining and living area. Additional family room with a wet bar and more dining space as well. Has multiple outdoor decks. Super convenient to the Blue Line if you want to take the train from O'Hare, and really easy to get downtown. Perfect for families, corporate retreats, or large groups.

ALOHA 2.0 | Patio, 2 Parking, Sleeps 23

Look no further for your ultimate city escape! Welcome to ALOHA 2.0 — a 2,000 sq ft vibrant oasis in the ❤️ of Wicker Park. This bold, design-forward retreat combines tropical flair, playful color, and urban luxury to create the perfect stay for large groups, celebrations, and unforgettable weekends in Chicago. Price to high? We understand! Please always reach out to us for a discount. We always want everyone to be able to experience a BANGTEL when possible!

Historic Wicker Park Penthouse - Prime Location!

Experience city living in this stylish 3BD/3BA duplex penthouse! - Private elevator opens to a bright living room with local artwork - Two spacious living rooms for relaxation and entertainment - Fully equipped kitchen with utensils and cookware - Two large decks with stunning Chicago skyline views - King-size pillow-top beds in all bedrooms - Outdoor patio with seating, grill, and fire pit Book your stay with TheDreamRentals today!

Cozy/Spacious WFH Family Friendly w Permit Parking

Bright first-floor private apartment with free parking passes for permit-only street parking. Enjoy the wide-open windows, a private outdoor space, and two bathtubs for ultimate relaxation. Cook for yourself in the fully-equipped kitchen or explore some of the amazing restaurants nearby. Family/baby friendly with included highchair, pack n' play, crib, baby monitor, and more!

Wicker Park 4BD Home: Parking, Theater, & Rooftop

Welcome to TheDreamRentals, an opulent 4-bedroom sanctuary in the city! - Grand foyer and spacious living areas - Chef's kitchen with top-of-the-line appliances - Five luxurious bedrooms with private retreats - State-of-the-art home theater for cinematic experiences - Two rooftop patio decks with panoramic city views Book your stay with TheDreamRentals today!

Paradise on the Park

Located in Chicago’s hot West Town neighborhood. This is a one bedroom one bath unit in a quiet nook directly on Smith Park. Access to the park across the street with pickle ball courts, tennis courts, baseball field, and picnic areas. Situated close to Wicker Park and Bucktown. Plenty of FREE street parking directly across the street on the park side of the street.